Category: 369-26-6

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 3-amino-4-fluorobenzoate

Into a 100-mL round-bottom flask, was placed methyl 3-amino-4-fluorobenzoate (1 g, 5.91 mmol), HCl (6 M, 10 mL). This was followed by the addition of a solution of NaNO2 (630 mg, 9.13 mmol) in water (2 mL) dropwise with stirring at 0oC. The resulting solution was stirred for 20 min at 0oC. The above mixture was added to a saturated solution of SO2 in AcOH (20 mL) and CuCl2 (800 mg, 5.95 mmol) dropwise with stirring at 0oC. The resulting solution was stirred for 1 h at RT. The reaction was then quenched by the addition of 20 mL of water. The resulting solution was extracted with 3×20 mL of ethyl acetate and the organic layers combined and dried over anhydrous Na2SO4, then concentrated under vacuum. This resulted in 1.5 g (crude) of the title compound as a yellow oil. The crude product was used in the next step.

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; IFM THERAPEUTICS, INC; GLICK, Gary; GHOSH, Shomir; ROUSH, William R.; (185 pag.)WO2017/184623; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8FNO2

Step 2: Methyl 4-fluoro-3-(imidazo[1 ,2-a]pyridine-3-carboxamido)benzoateA solution of methyl 3-amino-4-fluorobenzoate (5 g, 29.6 mmol) in pyridine (200 ml) was treated with imidazo[1 ,2-a]pyridine-3-carbonyl chloride. HCI (step 1 )(6.43 g, 29.6 mmol) and the mixture was stirred at RT for 2 days. The mixture was poured into water (30 ml) and a small exotherm was observed. After cooling to RT, the resulting precipitate was filtered and dried in a vacuum oven to afford the title compound; LC-MS: Rt 0.81 mins; MS m/z 314.2 {M+H}+; Method 2minl_C_v0031 H NMR (400 MHz, DMSO-d6) delta 10.30 (1 H, s), 9.44 (1 H, d), 8.63 (1 H s), 8.34 (1 H, dd), 7.83 (1 H, m), 7.78 (1 H, d), 7.54 (1 H, m), 7.48 (1 H, m), 7.20 (1 H, t), 3.90 (3H, s)

According to the analysis of related databases, 369-26-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; IRM LLC; BRUCE, Ian; CHAMOIN, Sylvie; COLLINGWOOD, Stephen Paul; FURET, Pascal; FURMINGER, Vikki; LEWIS, Sarah; LOREN, Jon Christopher; MOLTENI, Valentina; SAUNDERS, Alex Michael; SHAW, Duncan; SVIRIDENKO, Lilya; THOMSON, Christopher; YEH, Vince; JANUS, Diana; WEST, Ryan; WO2013/30802; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

369-26-6, name is Methyl 3-amino-4-fluorobenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: Methyl 3-amino-4-fluorobenzoate

POCI3 (44 mu, 0.470 mmol) was added to methyl 3-amino-4-fluorobenzoate (53.0 mg, 0.313 mmol) and 4-ethylbenzoic acid (47.0 mg, 0.313 mmol) in MeCN (2 ml) and the mixture was heated at 100 °C for 30 min. Solvents were evaporated and residue purified by flash chromatography using 10-20percent) EtOAc in hexanes. Yield: 18.5 mg (20percent>); white solid. The amide from above (18.5 mg, 0.061 mmol) and Lawesson’s reagent (32 mg, 0.078 mmol) in toluene (2 ml) was heated at 110 °C for 2 d. Solvent was evaporated and residue purified by flash chromatography using 20-35percent EtOAc in hexanes as eluent. Yield: 7.1 mg (39percent). Hydroxylamine potassium salt in MeOH (ca 1.7 M, 1.5 ml) was added to the ester from above and the mixture was heated at 60 °C for 45 min before quenched with AcOH (0.5 ml). The title compound was isolated by reversed phase chromatography (Kinetex CI 8, 5 muiotaeta, 21.2 x 100 mm, flow 25 ml/min, gradient 0.1percent TFA in water / acetonitrile over 15 minutes). Yield; 5.1 mg (72percent); white solid.

The synthetic route of 369-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KANCERA AB; HAMMER, Kristin; JOeNSSON, Mattias; KRUeGER, Lars; (230 pag.)WO2017/108282; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 369-26-6 as follows. name: Methyl 3-amino-4-fluorobenzoate

Methyl 3-amino-4-fluorobenzoate (2 g, 13 mmol) and pyridine (2.1 g, 76.4 mmol) were suspended in DCM (25 mL), and to the stirring solution was slowly added 2-trifluoromethyl- benzenesulfonyl chloride (3.24 g, 13 mmol) at room temperature. After stirring for 2 h, the reaction mixture was washed with water and then extracted with DCM. The combined organic layers were dried over Na2SOzI, filtered, and concentrated in vacuo. The crude residue was suspended in water (30 mL) followed by slow addition of NaOH (1.1 g, 28 mmol), and the mixture heated at reflux overnight. After cooling to room temperature, the reaction mixture was extracted with DCM. The layers were separated. The aq. layer adjusted to pH 5 with aq. 5N HCl, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford the final product as a solid (4.0 g, 83percent overall). LC-MS (ES) m/z = 364.1 (M+H)+ 1H NMR (400 MHz, DMSO-d6) delta ppm 10.61 (br, 1 H), 10.37 (br, 1 H), 8.78 (m, 1 H), 8.37 (m, 1 H), 8.01 (m, 2 H), 7.71 (m, 2 H), 7.31 (m, 2 H).

According to the analysis of related databases, 369-26-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; LAFRANCE, Louis, Vincent; LEBER, Jack, Dale; LI, Mei; VERMA, Sharad, Kumar; WO2010/126922; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 369-26-6, 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. 369-26-6, name is Methyl 3-amino-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a 40 mL reaction vessel was charged 8-chloro-N-(2-fluorobenzyl)-N-(2- hydroxyethyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamide (I-73) (0.10 mmol) and CH2Cl2 (10 mL) followed by the addition of commercial Dess-Martin Periodinane (Sigma- Aldrich, 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H-one, 0.20 mmol) and buffered with solid sodium bicarbonate (0.20 mmol). The milky white suspension was rapidly stirred for 2 hrs and then the reaction was then directly diluted with ethyl acetate (150 mL) and washed with water (3 x 15 mL). The resulting organic extract was concentrated to a residue (in vacuo) and used directly without delay or further manipulation. The residue was dissolved in 9:1 MeOH/AcOH (5 mL) and treated with methyl-3-amino benzoate (0.40 mmol). The resulting reaction was then stirred at room temperature for 30 mins. and then treated with sodium cyanoborohydride (1.0 mmol, portion-wise over 30 mins.) followed by stirring at room temperature for an additional 1 hr. The resulting reaction was diluted with ethyl acetate (150 mL) and washed with water (3 x 25 mL). The resulting organic extracts were concentrated in vacuo and then directly subjected to reverse phase chromatography using TFA-modified (0.05 percent) water/ACN (35 to 80 percent). All fractions were reduced to dryness under vacuum and subjected to a free base event using polymer immobilized carbonate (SPE-C03H Varian cartridge, 0.90 nominal load with MeOH mobilizer, 10 mL) to give methyl 3-((2-(8-chloro-N-(2- fluorobenzyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)ethyl)amino) benzoate (63-lnt) as a white solid. 1H NMR (400 MHz, d4-MeOH): delta 7.48-7.19 (m, 8H), 7.03- 6.92 (3H), 7.18 (app d, J = 8.0 Hz, 1 H), 6.62 (app dt, J = 12.2, 8.0 Hz, 1 H), 5.30-5.20 (m, 2H), 4.83 (br s, 2H), 4.21 (t, J = 5.0 Hz, 2H), 3.85 (s, 3H), 3.74 (s, 3H), 3.38 (t, J = 5.0 Hz, 2H). Mixture of rotamers. MS (m/z): 549.2/551.2 (M+H)+(chlorine isotope pattern).

The synthetic route of Methyl 3-amino-4-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; CHIANELLI, Donatella; LIU, Xiaodong; MOLTENI, Valentina; NELSON, John; ROLAND, Jason; RUCKER, Paul; TULLY, David; WO2015/69666; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 369-26-6, 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. 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture solution of 3-amino-4-fluoro-benzoic acid methyl ester (26 g, 153.8 mmol), 3-bromo-benzaldehyde (28.5 g, 153.8 mmol) and p-toluenesulfonic acid (590 mg, 3.2 mmol) in toluene (200 mL) was heated to reflux for 12 hours. Then the reaction mixture was cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 3-[(3-bromo-benzylidene)-amino]-4-fluoro-benzoic acid methyl ester (51.7 g, quant.) as a pale-white solid: MS calcd. for C15H11BrFlNO2 337.16, obsd. (ESI+) [(M+H)+] 336.0 338.0

The chemical industry reduces the impact on the environment during synthesis Methyl 3-amino-4-fluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chen, Li; Feng, Lichun; Huang, Mengwei; Liu, Yongfu; Wu, Guolong; Wu, Jim Zhen; Zhou, Mingwei; US2011/257151; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, 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. Recommanded Product: Methyl 3-amino-4-fluorobenzoate

To a solution of imidazo[1 ,2-a]pyridine-3-carboxylic acid (1 ) (10 g, 61 .73 mmol) in dichloromethane (300 ml_) was added DMF (2 ml_) and oxalyl chloride (18 g, 141 .73 mmol) at 0-10 °C. The resulting solution was stirred overnight at room temperature and concentrated under vacuum. The solid obtained was added into a solution of methyl 3- amino-4-fluorobenzoate (7) (10 g, 59.17 mmol) and TEA (20 g, 198.02 mmol) in dichloromethane portionwise. The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum and diluted with of methanol (250 ml_). The solids were collected by filtration and washed with sat. Na2C03 (2×200 ml_) and methanol (2×50 ml_) to yield methyl 4-fluoro-3-(imidazo[1 ,2-a]pyridine-3- carboxamido)benzoate (8) as a light yellow solid.

The synthetic route of Methyl 3-amino-4-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; NOVARTIS PHARMACEUTICALS UK LIMITED; LIANG, Fang; GIBNEY, Michael; YEH, Vince; LI, Xiaolin; MOLTENI, Valentina; SHAW, Duncan; BERMAN, Ashley Mitchell; LEWIS, Sarah; LOREN, Jon; FURMINGER, Vikki; WO2013/33620; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 369-26-6, Computed Properties of C8H8FNO2

To the solution of compound 7-bromoimidazo[1,2-a]pyridine-3-carboxylic acid (Intermediate 1) (1.26 Kg, 5.23 mol) in DMAC (15 L) was added dropwise SOCl2 (1.86 kg, 15.6 mol) at 10 °C in 30 min. To the resulting mixture warmed to 20°C was added compound methyl 3-amino-4-fluorobenzoate (884 g, 5.23 mol) in DMAC (3.0 L) over 30 min. After addition, the reaction temperature went up to 30 °C. HPLC showed the reaction went to completion within 5 min. To the reaction mixture was added water (20 L) over 20 min. The mixture was filtered and dried under vacuum to afford the title compound as a white solid; 1 H NMR (400 MHz, DMSO-d6) delta 3.87 (s, 3 H) 7.57 (dd, J=7.28, 2.01 Hz, 1 H) 7.51 (dd, J=10.16, 8.66Hz, 1 H) 7.90 (td, J=4.33, 2.38 Hz, 1 H) 8.29 (m, 2H) 8.90 (s, 1 H) 9.43 (d, J=7.53 Hz, 1 H) 10.78 (s, 1 H) Rt 6.90 mins; MS m/z 394.0 {M+H}+; Method 10 min LC

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; NOVARTIS AG; BRUCE, Ian; CHAMOIN, Sylvie; COLLINGWOOD, Stephen Paul; FURET, Pascal; FURMINGER, Vikki; LEWIS, Sarah; LOREN, Jon; LV, Lin; MOLTENI, Valentina; SAUNDERS, Alex Michael; SHAW, Duncan; TURNER, Roy; YEH, Vince; WO2014/132220; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 369-26-6, These common heterocyclic compound, 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, 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.

HATU (116 mg, 0.305 mmol) was added to picolinic acid (37.5 mg, 0.305 mmol) and DIPEA (66 mu, 0.381 mmol) in DMF (2 ml). After 15 min, methyl 3-amino-4-fluorobenzoate (43 mg, 0.254 mmol) in DMF (1 ml) was added. The mixture was stirred at ambient temperature for 10 d before solvent was evaporated and residue dissolved in EtOAc. The solution was washed with sat. NaHC03, dried (MgS04) and evaporated. Half of the crude material from above (0.127 mmol) was dissolved in dioxane (1.5 ml) and MeCN (1.5 ml). Potassium carbonate (35 mg, 0.254 mmol) was added and the mixture was heated at 180 ¡ãC for 2 h in a microwave reactor. Silica gel was added and solvents evaporated. The dry silica was applied on a flash column which was eluted with 35-50percent) EtOAc in hexanes. Yield: 6 mg (18percent>); colourless oil.

Statistics shows that Methyl 3-amino-4-fluorobenzoate is playing an increasingly important role. we look forward to future research findings about 369-26-6.

Reference:
Patent; KANCERA AB; HAMMER, Kristin; JOeNSSON, Mattias; KRUeGER, Lars; (230 pag.)WO2017/108282; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 369-26-6,Some common heterocyclic compound, 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, molecular formula is C8H8FNO2, 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.

Intermediate 37: 2-Propen-1-yl {5-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}carbamate; Step A: Methyl 4-fluoro-3-{[(2-propen-1-yloxy)carbonyl]amino}benzoate; To a solution of methyl 3-amino-4-fluorobenzoate (109 g, 644 mmol) in THF (2000 mL), saturated NaHCO3 (68 g, 805 mmol) was added. Then 2-propen-1-yl chloridocarbonate (93 g, 773 mmol) was added dropwise at 0 C. The mixture was stirred at rt for 2 h. The solution was extracted with EtOAc (500 mL¡Á3). The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product (160 g, 98%), which was used in the next step directly. 1H NMR (400 MHz, CDCl3) delta ppm 8.72-8.81 (m, 1H), 7.71-7.79 (m, 1H), 7.09-7.16 (m, 1H), 6.87-6.94 (br, 1H), 5.91-6.03 (m, 1H), 5.41 (d, J=17.1 Hz, 1H), 5.28 (d, J=10.5, 1H), 4.70 (d, J=10.5 Hz, 1H), 4.70 (d, J=5.5 Hz, 2H), 3.90 (s, 3H).

The synthetic route of 369-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics