Sources of common compounds: Methyl 3-(4-fluorophenyl)propiolate

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 42122-44-1.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 3-(4-fluorophenyl)propiolate

To a solution of N-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide (9.0 g, 30.0 mmol) in DCM (100 mL) was added (O-(mesitylsulfonyl)hydroxylamine) (20 g, 92 mmol) in DCM (20 mL) dropwise quickly at 0C under N2, and stirred for 2 h at room temperature. After concentrated and the residue was dissolved in MeOH, and re-concentrated again. The residue was dissolved in DMF (20 mL), and then added slowly dropwise to a mixture of methyl 3-(4-fluorophenyl)propiolate (6 g, 34 mmol) and K2C03 (21 g, 154 mmol) in DMF (100 mL) at 0C under N2. The mixture was stirred overnight at room temperature. The reaction mixture was then concentrated in vacuo and the resulting residue was suspended in H20 and extracted with DCM. The organic layer was washed with H20, brine and concentrated in vacuo. The residue obtained was purified using flash column chromatography on silica gel (eluted with PE / EtOAcfrom 5 / 1 to 3 / 1) to give methyl 5-(benzyloxy)-2-(4-fluorophenyl)-6-(N-methylmethylsulfonamido)pyrazolo [1 ,5-a]pyridine-3 -carboxylate (3.5 g, yield: 24%). ?H-NMR(CDC13, 400 MHz) oe 8.54 (s, 1H), 7.70-7.74 (m, 2H), 7.68 (s, 1H), 7.42-7.44 (m, 5H), 7.13 (t, J= 8.8 Hz, 2H), 5.24 (s, 2H), 3.80 (s, 3H), 3.29 (s, 3H), 2.81 (s, 3H). MS (M+H): 484.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 42122-44-1.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda, L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/123793; (2014); A1;,
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Introduction of a new synthetic route about 42122-44-1

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Related Products of 42122-44-1, A common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, molecular formula is C10H7FO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a cooled solution (0 C, ice bath) containing 3-(3-(N-(2-(tert- butyldimethylsilyloxy)ethyl)methylsulfonamido)pyridin-4-yl)-N-(2-phenylpropan-2- yl)benzamide (0.090 g, 0.12 mmol) and dichloromethane (2 mL) was added O- (mesitylsulfonyl)hydroxylamine (0.080 g, 0.37 mmol) in dichloromethane (2 mL) quickly, dropwise. The solution was maintained at 0 C for 15 min, removed from the cooling bath and maintained at ambient temperature for 2 h. The solution was concentrated, dissolved in methanol (5 mL) and re-concentrated to afford l-amino-3- ( -(2-hydroxyethyl)methylsulfonamido)-4-(3-(2-phenylpropan-2- ylcarbamoyl)phenyl) pyridinium 2,4,6-trimethylbenzenesulfonate as a light yellow foam (470, MH+). The product thus obtained was dissolved in DMF (2.4 mL) and added slowly dropwise over 20 min to a cooled mixture (0C, ice bath) containing potassium carbonate (0.070 g, 0.50 mmol), methyl 3-(4-fluorophenyl)propiolate (0.030 g, 0.19 mmol) and DMF (2.0 mL). The mixture was kept in the cooling bath with stirring and allowed to proceed for 15 h at ambient temperature. The mixture was filtered and concentrated. Purification on silica gel (0-100% ethylacetate/hexanes, 60 min gradient) afforded methyl 2-(4-fluorophenyl)-6-( -(2- hydroxyethyl)methylsulfonamido)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl) pyrazolo[l,5-a]pyridine-3-carboxylate as a yellow residue. 1H NMR (500 MHz,CHLOROFORM-D) delta ppm 8.72 (s, 1 H), 8.24 (s, 1 H), 8.16 (s, 1 H), 7.97 – 8.00 (m, 1 H), 7.89 (t, J=7.93 Hz, 1 H), 7.77 – 7.84 (m, 2 H), 7.50 – 7.59 (m, 2 H), 7.40 – 7.49 (m, 3 H), 7.23 – 7.33 (m, 3 H), 7.12 – 7.19 (m, 3 H), 3.83 (s, 3 H), 3.62 – 3.71 (m, 1 H), 3.39 – 3.46 (m, 1 H), 3.30 – 3.39 (m, 1 H), 3.18 – 3.23 (m, 3 H), 2.63 – 2.72 (m, 1 H), 1.78 (t, J=12.21 Hz, 6 H). LCMS: retention time: 2.403 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters- Sunfire, 5u, CI 8, 4.6 x 50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3CN / 90% H20 / 10 mM TFA and solvent B was 10% H20 / 90% CH3CN / 10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode, m/z 645 (MH+).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PRACITTO, Richard; KADOW, John, F.; BENDER, John, A.; BENO, Brett, R.; GRANT-YOUNG, Katharine; HAN, Ying; HEWAWASAM, Piyasena; NICKEL, Andrew; PARCELLA, Kyle, E.; YEUNG, Kap-Sun; CHUPAK, Louis, S.; WO2011/112186; (2011); A1;,
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New learning discoveries about C10H7FO2

The synthetic route of 42122-44-1 has been constantly updated, and we look forward to future research findings.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C10H7FO2

The product thus obtained was dissolved in DMF (2,4 mL) and added slowly dropwise over 20 min to a cooled mixture (00C, ice bath) containing potassium carbonate (0.070 g, 0.50 mmol), methyl 3-(4-fluorophenyl)propiolate (0.030 g, 0.19 mmol) and DMF (2.0 mL). The mixture was kept in the cooling bath with stirring and allowed to proceed for 15 h at ambient temperature. The mixture was filtered and concentrated. Purification on silica gel (0-100% ethyl acetate/hexanes, 60 min gradient) afforded methyl 2-(4-fluorophenyl)-6-(N-(2- hydroxyethyl)methylsulfonamido)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl) pyrazolo[lj5-a]pyridme-3-carboxylate as a yellow residue. IH NMR (500 MHz, CHLOROFORM-D) delta ppm 8.72 (s, 1 H), 8.24 (s, 1 H), 8.16 (s, 1 H), 7.97 – 8.00 (m, 1 H), 7.89 (t, J-7.93 Hz, 1 H), 7,77 – 7.84 (m, 2 H), 7.50 – 7.59 (m, 2 H)5 7.40 – 7.49 (m, 3 H), 7.23 – 7.33 (m, 3 H)9 7.12 – 7.19 (m, 3 H), 3.83 (s, 3 H), 3.62 – 3.71 (m, 1 H), 3.39 – 3.46 (m, 1 H), 3.30 – 3.39 (m, 1 H), 3.18 – 3.23 (m, 3 H), 2.63 – 2.72 (m, 1 H), 1.78 (t, J=I 2.21 Hz, 6 H). LCMS: retention time: 2.403 min. LC data was recorded on a Shimadzu LC-IOAS liquid chromatograph equipped with a Waters- Sunfre, 5u, C 18, 4.6 x 50 mm column using a SPD-10AV UV- Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3CN / 90% H2O / 10 mM TFA and solvent B was 10% H2O / 90% CH3CN / 10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode, m/z 645 (MH+).

The synthetic route of 42122-44-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PRACITTO, Richard; KADOW, John F.; BENDER, John A.; BENO, Brett R.; GRANT-YOUNG, Katharine A.; HAN, Ying; HEWAWASAM, Piyasena; NICKEL, Andrew; PARCELLA, Kyle E.; YEUNG, Kap-Sun; CHUPAK, Louis S.; WO2010/30538; (2010); A2;,
Ester – Wikipedia,
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Research on new synthetic routes about Methyl 3-(4-fluorophenyl)propiolate

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 42122-44-1.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 3-(4-fluorophenyl)propiolate

To a stirred solution of 1-aminopyridin-l-ium 2,4-dinitrophenolate (3.7 g, 13.30 mmol) and Intermediate 59A (2.4 g, 13.47 mmol) in THF (25 mL) was added DBU (4.06 mL, 26.9 mmol) dropwise at 0 C over a period of 10 min. and the resulting brown color solution was stirred at RT for 12 h. THF was removed completely under reduced pressure, crude product was diluted with water (100 mL) and the aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined the organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified by silica gel chromatography (40 g REDISEP column, eluting with 2% methanol in chloroform). Collected fractions were concentrated together to afford Intermediate 59B (2.7 g, 74%) as a yellow solid. MS(ES): m/z = 271 [M+H]; 1H NMR (400 MHz, chloroform-d) delta ppm 8.52 (dd, J= 6.90, 1.07 Hz, 1H), 8.20 (dd, J= 8.94, 1.04 Hz, 1H), 7.76 – 7.85 (m, 2H), 7.43 (ddd, J= 8.97, 6.90, 1.07 Hz, 1H), 7.09 – 7.21 (m, 2H), 6.98 (td, J= 6.89, 1.22 Hz, 1H), 3.82 – 3.89 (m, 3H)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 42122-44-1.

Reference:
Patent; KARUPPIAH Arul Mozhi Selvan Subbiah; KUMARAVEL Selvakumar; MAHESHWARAPPA Shilpa Holehatti; RACHAMREDDY Chandrasekhar Reddy; VELAPARTHI Upender; WITTMAN Mark D; WO2015/195880; (2015); A1;,
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The important role of C10H7FO2

Some common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, molecular formula is C10H7FO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: Methyl 3-(4-fluorophenyl)propiolate

Some common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, molecular formula is C10H7FO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: Methyl 3-(4-fluorophenyl)propiolate

To a solution ofN-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide (9.0 g, 30.0mmol) in DCM (100 mL) was added (0-(mesitylsulfonyl)hydroxylamine) (20 g, 92 mmol) inDCM (20 mL) dropwise quickly at 0C under N2, and stirred for 2 hat room temperature. Afterconcentrated and the residue was dissolved in MeOH, and re-concentrated again. The residuewas dissolved in DMF (20 mL), and then added slowly dropwise to a mixture ofmethyl3-(4-15 fluorophenyl)propiolate (6 g, 34 mmol) and K2C03 (21 g, 154 mmol) in DMF (100 mL) at 0Cunder N2 . The mixture was stirred overnight at room temperature. The reaction mixture wasthen concentrated in vacuo and the resulting residue was suspended in H20 and extracted withDCM. The organic layer was washed with H20, brine and concentrated in vacuo. The residueobtained was purified using flash column chromatography on silica gel (eluted with PE I EtOAc20 from 5 I 1 to 3 I 1) to give methyl 5-(benzyloxy)-2-( 4-fluorophenyl)-6-(Nmethylmethylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxylate (3.5 g, yield: 24%). 1H-NMR(CDCh, 400 MHz) 8 8.54 (s, 1H), 7.70~7.74 (m, 2H), 7.68 (s, 1H), 7.42~7.44 (m, 5H), 7.13 (t, J= 8.8 Hz, 2H), 5.24 (s, 2H), 3.80 (s, 3H), 3.29 (s, 3H), 2.81 (s, 3H). MS (M+Ht: 484.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 42122-44-1, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/121416; (2014); A1;,
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The important role of 42122-44-1

According to the analysis of related databases, 42122-44-1, the application of this compound in the production field has become more and more popular.

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 42122-44-1 as follows. category: esters-buliding-blocks

Example 2.42- (4-Fluoro-phenvl)-6-methanesulfonvl-3- (4-methanesulfonyl-phenyl)-pyrazolof 1. 5-blpvridazine(i) 2- (4-Fluoro-phenvl)-6-methvlsulfanvl-pyrazolo1, 5-blpvridazine-3-carboxvlic acid methyl ester Solidt-butoxycarbonyl-O-mesitylenesulfonylhydroxylamine’ (7. 8g) was added portionwise with stirring to TFA (25mL) over 10min then stirred for a further 20 minutes. The solution was poured onto ice(-200mL) and left until the ice melted. The resulting white solid was filtered off, washed with water, and dissolved in DME(100mL). The solution was dried over 4A mol. sieves for 1.5 hours, filtered then added to a solution of3-methylthio-pyridazine2 (2.6g) indichloromethane (35mL) and the reaction stirred at room temperature for 20h. The intermediate salt was isolated by filtration as light brown crystals (3. 87g), suspended in acetonitrile(100mL) and methyl3- (4-fluoro-phenyl)-prop-2-ynoic acid (2. 02g) added. 1,8- Diazabicyclo [5.4. 0] undec-7-ene (2. 1mL) was added dropwise and the reaction was stirred at room temperature for 20 hours. The resulting crystalline precipitate was filtered off, washed and dried (770mg). Concentration of the filtrate gave a second crop (430mg). The residues were partioned between water and ethyl acetate(100mL each) and the aqueous layer was extracted with ethyl acetate (20mL). The combined organics were washed with water, brine and dried. Removal of solvent gave a brown oil which was purified by flash chromatography on silica (300g) eluting with cyclohexane/ethyl acetate (3: 1) to give a further quantity of product (247mg). The three crops were combined to give the title compound (1.45g) as a light brown solid.

According to the analysis of related databases, 42122-44-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/48999; (2005); A2;,
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Extracurricular laboratory: Synthetic route of 42122-44-1

The synthetic route of 42122-44-1 has been constantly updated, and we look forward to future research findings.

Reference of 42122-44-1,Some common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, molecular formula is C10H7FO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

c Methyl 2-(4-fluorophenyl)-pyrazolo[1,5-a]pyridine-3-carboxylate A stirred solution of methyl 3-(4-fluorophenyl)propiolate (8.02 g, 45 mmol) and 1-aminopyridinium iodide (10 g, 45 mmol) in dry acetonitrile (150 mL) was cooled to about 0 C. A solution of 1,8-diazabicycloundec-7-ene (13.7 g, 90 mmol) in dry acetonitrile (50 mL) was added dropwise over 1 h. The mixture was allowed to stir at room temperature for about 18 h. The reaction mixture was cooled in an ice bath for about 30 min and the precipitate was collected by filtration and washed with cold acetonitrile (10 mL). The solid was dried under reduced pressure to give the title compound as a white solid, 8.48 g (70%). 1H NMR (CDCl3) delta 8.50 (d, 1H, J=8.4 Hz), 8.18 (d, 1H, J=8.8 Hz), 7.78 (m, 2H), 7.42 (t, 1H, J=8.4 Hz), 7.13 (t, 2H, J=8.8 Hz), 6.97 (td, 1H, J=6.8, 1 Hz). MS (+ve ion electrospray) 271 (100), (MH+).

The synthetic route of 42122-44-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alberti, Michael John; Baldwin, Ian; Cheung, Mui; Cockerill, Stuart; Harris, Philip; Jung, David; Peckham, Gregory; Peel, Michael; Badiang, Jennifer; Stevens, Kirk; Veal, James; US2004/53942; (2004); A1;,
Ester – Wikipedia,
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A new synthetic route of 42122-44-1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 42122-44-1, its application will become more common.

Some common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, molecular formula is C10H7FO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 42122-44-1

EXAMPLE 1 Intermediate A To a solution of methyl 4-(fluorophenyl)propynoate (J. Org. Chem. 1987, 52(16), 3662-8) (13 g, 73 mmol) in methanol (60 ml) was added water (60 ml) followed by methylhydrazine (4 ml, 77 mmol), the mixture was stirred for 6 hrs at 60 C. then left to stand overnight. The solid was filtered and washed with water then a minimum volume of methanol and dried overnight, affording 7.7 g of 5-(4-fluorophenyl)-1-methyl-1,2-dihydropyrazol-3-one (55%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 42122-44-1, its application will become more common.

Reference:
Patent; Castro Pineiro, Jose Luis; Collins, Ian James; Harrison, Timothy; US2005/143369; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Research on new synthetic routes about 42122-44-1

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 42122-44-1.

These common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 42122-44-1

To a stirred solution of the product of Step AD2 (9 g, 0.05M) in dry toluene (90 ml) under nitrogen, nitro ethane (8.5 ml, 0.050M) was added, followed by triethylamine (3.4 ml, 0.025M). Then a solution of phenyl isocyanate (6 g, 0.05M) in dry toluene was added to the RM at 80 C. After the addition was over the stirring was continued for overnight at 80 C. The RM was cooled under ice bath, filtered and the filtrate was concentrated under vacuum. The resulting mass was taken in ethyl acetate (75 ml) and washed with water (2¡Á20 ml), 5% NH4OH (40 ml), dried over anhydrous sodium sulphate and concentrated under vacuum to get crude product which was purified by column chromatography over silica gel (60-120) using PE/EtOAC (9.9/0.1) as eluent to afford isoxazole ester 3.7 g (32%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 42122-44-1.

Reference:
Patent; Gerritz, Samuel; Shi, Shuhao; Zhu, Shirong; US2006/287287; (2006); A1;,
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