Month: July 2021

These common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, 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. Application In Synthesis of Methyl 3-bromopropiolate

To a stirring solution of1,8-dihydroxynaphthalene (2) (1.74 g, 10.9 mmol) and methyl 3-bromopropiolate32 (2.65 g, 16.3 mmol)in anhydrous CH2Cl2 (40 mL) was added DABCO (2.66 g, 21.8 mmol) at 0 C under an argon atmosphere.After being stirred at room temperature for 3 h, the reaction mixture was treated with 1 M aqueous HCl.The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with brine,dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel chromatographyeluting with 25% EtOAc/hexane to yield the title compound (2.17 g, 8.96 mmol, 82%) as a white solid. Rf0.34 (20% EtOAc/hexane). Mp 115-118 C. IR nu (neat, cm-1): 1721, 1654, 1602, 1419, 1381, 1281, 1248,1131, 1089, 815, 799, 753. 1H-NMR (400 MHz, CDCl3): delta 7.52 (d, J = 8.3 Hz, 1H), 7.51 (d, J = 8.3 Hz,1H), 7.45 (dd, J = 8.3, 7.6 Hz, 1H), 7.42 (dd, J = 8.3, 7.3 Hz, 1H), 7.13 (d, J = 7.3 Hz, 1H), 6.93 (d, J =7.6 Hz, 1H), 4.97 (s, 1H), 3.75 (s, 3H). 13C-NMR (100 MHz, CDCl3): delta 166.2, 158.6, 144.4, 144.1, 133.6,128.0, 127.8, 121.9, 121.7, 110.6, 108.4, 107.6, 78.2, 50.9. HRMS (ESI, [M+H]+): calcd for C14H11O4,243.0652; found, 243.0653

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

Reference:
Article; Tsukamoto, Hirokazu; Nomura, Yumi; Doi, Takayuki; Heterocycles; vol. 99; 1; (2019); p. 549 – 565;,
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Application of 4911-54-0,Some common heterocyclic compound, 4911-54-0, name is Ethyl 4-methylpent-4-enoate, molecular formula is C8H14O2, 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 flame-dried flask that was purged under argon for 20 min was added LiAlH4 followed by 150 mL of anhydrous THF. The reaction mixture was cooled to 00C and a solution of compound 7 in THF (20 mL) was added slowly. The resulting solution was allowed to warm to room temperature and was stirred for 3 h until the starting material was completely consumed as indicated by TLC. The reaction was quenched by slow addition of the mixture to 300 mL of ice cold IM NaOH. The mixture was then allowed to stir for another hour and was filtered through Celite. A large amount of diethyl ether was used for rinsing. The filtrate was treated with water and extracted twice with diethyl ether. The combined organic phase was dried over Na2SO4 and evaporated in vacuo to give a residue which was purified via distillation at 20 mm Hg (bp 65-68 0C) to afford compound 8 as a yellow oil (9.5 g, 0.095 mol, 79%) (Mazzocchi et al. (1983) J. Org. Chem. 48, 2981-2989).1H NMR (500 MHz, CDCl3) delta 1.47 (br, IH), 1.69-1.74 (m, 5H), 2.1 (t, J = 7.5 Hz, 2H), 3.66 (t, J = 6.5 Hz, 2H), 4.71 (d, J = 0.8 Hz, IH), 4.73 (d, J = 0.8 Hz, IH), 4.73 (d, J = 0.4 Hz, IH); 13C NMR (125 MHz, CDCl3), delta 22.22, 30.41, 33.98, 62.64, 1 10.08, 145.40.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-methylpent-4-enoate, its application will become more common.

Reference:
Patent; PARHAMI, Farhad; KIM, Woo-Kyun; WO2008/82520; (2008); A2;,
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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. 57486-67-6, name is Methyl 2-(2-fluorophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 2-(2-fluorophenyl)acetate

21.4 ml (21.4 mmol) of lithium hexamethyldisilazide (1.0 M in THF) were initially charged in THF (30 ml) under argon and a solution of 3.00 g (17.8 mmol) of methyl 2-fluorophenylacetate in THF (15 ml) was added dropwise at -78 C. The reaction mixture was stirred at -78 C. for 1 h, and then a solution of 3.80 g (21.4 mmol) of the compound from example 1A in THF (15 ml) was added dropwise. The solution was stirred at -78 C. for 1 h, then brought to RT, and saturated aqueous ammonium chloride solution was added in portions. The mixture was diluted with water and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was stirred with MTBE, the solid was filtered off and the filtrate was concentrated. Silica gel chromatography (mobile phase: cyclohexane-ethyl acetate: 30:1, 20:1) of the residue gave 3.66 g (87% pure, 57% of theory) of the title compound. The crude product was reacted without further purification. [0195] LC-MS (method 1): Rt=1.05 min; MS (ESIpos): m/z=310 (M+H)+. [0196] 1H NMR (400 MHz, DMSO-d6): delta=3.66 (s, 3H), 6.25 (s, 1H), 7.20-7.28 (m, 4H), 7.31-7.38 (m, 1H), 8.15-8.23 (m, 1H), 8.68-8.71 (m, 1H).

According to the analysis of related databases, 57486-67-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Follmann, Markus; Stasch, Johannes-Peter; Redlich, Gorden; Ackerstaff, Jens; Griebenow, Nils; Knorr, Andreas; Wunder, Frank; Li, Volkhart Min-Jian; Mittendorf, Joachim; Schlemmer, Karl-Heinz; Jautelat, Rolf; US2013/267548; (2013); A1;,
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Electric Literature of 623-47-2, These common heterocyclic compound, 623-47-2, name is Ethyl 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.

To 2 mL of CH2Cl2 were added 1 mmol of arylboronic acid and1.2 mmol of terminal alkyne, then 0.01 mmol of palladium nanoparticles(1 mol%), 0.1 mmol of PPh3 (10 mol%), 1 mmol of Ag2O and 2 mmol of Cs2CO3 were added in turn. The mixture was heated at 35 C with stirring under a nitrogen atmosphere for the appropriate time (see Table 2, monitored by TLC or GC) till reaction was completed, then centrifuged. The solution was separated and the precipitate was washed with ether (5 mL x 3). The solutions were combined and washed with water, dried over anhydrous Na2SO4 and purified by column chromatography on silica gel with hexaneeethyl acetate (10:1) as eluent to yield the product. The precipitate was further washed sufficiently with methanol and ether, then dried, and the palladium nanoparticles were recovered.

The synthetic route of 623-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nie, Xiaopeng; Liu, Suli; Zong, Yan; Sun, Peipei; Bao, Jianchun; Journal of Organometallic Chemistry; vol. 696; 8; (2011); p. 1570 – 1573;,
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Reference of 139911-28-7,Some common heterocyclic compound, 139911-28-7, name is Ethyl 2-bromo-5-fluorobenzoate, molecular formula is C9H8BrFO2, 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.

Ethyl 2-(2-Methyl-4-fluorophenyl)-5-fluorobenzoate Tetrakis(triphenylphosphine)palladium(0) (0.02 eq, 0.31 g) was added to a vigorously stirred solution of ethyl 2-bromo-5-fluorobenzoate (1.0 eq, 3.3 g, 0.013 mol) and 2-methyl-4-fluorophenylboronic acid (1.2 eq, 0.016 mol, 2.4 g) in 45 mL of toluene, 22 mL of 2M aqueous sodium carbonate, and 11 mL of ethanol and the mixture was refluxed for 9 h. The cooled reaction mixture was poured into 50 mL each of water, ammonium hydroxide, and 2M aqueous sodium bicarbonate and then filtered through Celite. The filtrate was extracted with ethyl acetate and the organics were dried (MgSO4) and concentrated to yield 3.9 g of a yellow oil. Chromatography (silica gel, 20% ethyl acetate/hexane) gave 3.4 g (92%) of product as a light colored oil. 1 H NMR (CDCl3, 60 mHz) delta 7.7 (dd, 1 H), 7.5 (m, 1 H), 7.25- 6.75 (m, 4 H), 4.0 (q, 2 H), 2.0 (s, 3 H), 1.0 (t, 3 H); IR (CDCl3 solution) 3130, 2220, 1700, 1450, 1080 cm-1; MS m/z 276 (M+), 201 (base peak).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-bromo-5-fluorobenzoate, its application will become more common.

Reference:
Patent; Alcon Laboratories, Inc.; US5070100; (1991); A;,
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Electric Literature of 25597-16-4, These common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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.

[0530] To a solution of 3-CHLORO-6-HYDROXY-2, 4-dimethylbenzaldehyde (6.9 g, 37.4 mmol) in 80 mL of DMF was added dried finely powdered K2CO3 (11.36 g, 82.2 mmol). With mechanical stirring, the reaction was heated to 65 C. To the suspension was added dropwise ethyl trifluorocrotonate (7.54 g, 44.9 mmol). The stirring reaction was heated at 90 C for 1.5 h. K2C03 was filtered from the cooled reaction. From the reaction under vacuum, DMF was removed. The resulting residue was dissolved in 400 mL EtOAc. The organic solution was washed with 100 mL 1 M KHS04, 70 mL OF SATD. KHC03, 100 mL brine, followed by drying over MGS04, and concentrating under vacuum. The crude desired product (13.8 g) of was isolated. After employing flash chromatography conditions, pure compound (9.8 g, 78 %) of was isolated and its structure confirmed by NMR and LC-MS.

Statistics shows that Ethyl 4,4,4-trifluorocrotonate is playing an increasingly important role. we look forward to future research findings about 25597-16-4.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
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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. 24398-88-7, name is Ethyl 3-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H9BrO2

EXAMPLE 11. Synthesis of Ethyl 3-(5-Aminopyrimidin-2-ylamino)Benzoate(Intermediate 6); [0140] To a solution of 2-amino-5-nitropyrimidine (550 mg, 3.9 mmol) in 35 mL anhydrous 1,4-dioxane were added ethyl 3-bromobenzoate (1.8 g, 7.9 mmol), Xantphos, (230 mg, 0.4 mmol), Pd2(dba)3 (180 mg, 0.2 mmol) and Cs2CO3 (2.6 g, 8 mmol). The reaction mixture was stirred at 1000C for 5 h under argon. The solvent was removed under reduced pressure. The resulting solution was extracted with CHCl3 (3 x 50 mL) and saturated NaHCO3 (50 mL). The organic layer was separated, washed with brine, dried over Na2SO4 and filtered. The organic solvent was removed and the crude product was purified by silica gel column with CHCl3 as an eluent. The precipitated yellow solid was isolated by washed with chloroform and dried in vacuo (700 mg, 62%). 1H NMR (DMSO- de): delta 1.33 (t, J= 7.1 Hz, 3H), 4.33 (q, J = 7.1 Hz, 2H), 7.54 (t, J = 8.0 Hz, IH), 7.60-7.90 (m, IH), 7.95-8.10 (m, IH), 8.37 (t, J= 1.9 Hz, IH)3 9.26 (s, 2H)5 11.00 (s, IH).[0141] The above product was hydrogenated in 100 mL methanol/ethyl acetate (v/v: 1:1) using Pd/C (10%, 1 g) for 2 h. The palladium catalyst was removed by filtration, and the solvent was evaporated. The crude product was purified by silica gel column with 5% CH3OH / CHCl3 as an eluent to yield an off-white solid. MS (ES+): m/z 259 (M+H)+.

According to the analysis of related databases, 24398-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TARGEGEN, INC.; WO2008/8234; (2008); A1;,
Ester – Wikipedia,
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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. 14064-10-9, name is Diethyl 2-chloromalonate, A new synthetic method of this compound is introduced below., SDS of cas: 14064-10-9

Step 1: 3,4-Dihydro-3-oxo-2H-pyrido[3,2-b]-1,4-oxazin-2-carboxylic Acid Ethyl Ester. Diethyl chloromalonate (9.73 g, 50 mmol) was added to a stirred mixture of 3-hydroxy-2-aminopyridine (5.51 g, 50 mmol), triethylamine (6.97 mL, 50 mmol) and EtOH (100 mL) at room temperature. The mixture was heated at reflux for 17 h and allowed to attain room temperature. The precipitate formed was filtered off, washed with EtOH and dried to give the product as a white solid: yield 3.85 g (35percent); mp 160-162° C. Anal. (C10H10N2O4) C, H, N.

The synthetic route of 14064-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Biovitrum AB; US6465467; (2002); B1;,
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Synthetic Route of 40876-98-0, These common heterocyclic compound, 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, 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.

General procedure: A mixture of compound 1 (1 equiv) and aldehyde (1 equiv) together with an equimolar amount of amine in ethanol was refluxed towards completion (0.5 – 2 hours). Iced-water was added to the mixture after cooling and HCl was then added dropwise to pH 1. Filter the solid while appear. Traces aldehyde in the crude product was washed with water and ether to give (4a-k). Ethyl 4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate (4a) White solid; 60%; m.p. 106-109oC. IR (ATR) n/cm-1: 3344 (OH), 2986 (NH, amide), 1782 (C=O, ester), 1687 (C=C), 1670 (-N-C=O, amide), 1302 (C-N); 1H-NMR (400 MHz, CDCl3): delta 4.91-4.85 (2H, s, CH2), 4.39-4.32 (2H, q, J= 7.2 Hz, CH2), 1.38-1.31 (3H, t, J= 7.1 Hz, CH3); 13C-NMR (100 MHz, CDCl3,): delta 166.54 (COH), 164.23 (C=O) 151.29 (C=O), 116.09 (quat. C), 66.26 (OCH2), 62.09 (CH2), 14.34 (CH3); Anal. Calcd. for C7H9NO4: C, 49.12; H, 5.30; N, 8.18; O, 37.39. Found: C, 49.30; H, 4.65; N, 7.04; O, 39.01; GCMS m/z(EI, + ve): found 172.00 ([M]+), C7H9NO4 calculated 172.06

The synthetic route of 40876-98-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bacho, Muhamad Zulfaqar; Hamzah, Ahmad Sazali; Kamarulzaman, Firdaus; Mohammat, Mohd Fazli; Shaameri, Zurina; Wibowo, Agustono; Oriental Journal of Chemistry; vol. 36; 2; (2020); p. 309 – 319;,
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Reference of 457097-93-7, A common heterocyclic compound, 457097-93-7, name is Methyl 4-amino-3-(trifluoromethoxy)benzoate, molecular formula is C9H8F3NO3, 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 500 mL round-bottom t1ask was added methyl4-amino-3-(trifluoromethoxy)5 benzoate (7.1 g, 30.19 mmoL 1.0 equiv.), AcOH (100 mL), and NaSCN (12.1 g, 149.25mmol, 5.0 equiv .), followed by the dropwise addition of a solution of bromine (9.6 g, 60.07mrnol, 2.0 equiv.) in AcOH (50 rnL) at 0 C over 1 hr. The mixture vvas stirred at 0 C for 2h, and then at 40 C overnight The reaction mixture vas cooled to 0 C, and a second batchofNaSCN (12.2 g, 150.49 mmol, 5.0 equiv.) was added, followed by the dropwise addition10 of a solution of bromine (9.6 g, 60.07 mmol, 2 0 equiv.) in AcOFf (50 mL) over l hr. Again,the reaction mixture was stirred at 0 C tor 2 h, and then at 40 C for 3 days. The resultingmixture was diluted Vith 200 mL of water and the pH value of the aqueous solution wasadjusted to 9 with sodium hydroxide. The resulting solids were collected by filtration,·washed ·with ·water (20 mL x 2), and dried in an oven at 60 C for 6 h to provide of rnethyl 2-15 amino-4-(trifluoromethoxy)-1 ,3-benzothiazole-6-carboxy late A-4b (54 g, 61 %) as a brornsolid.

The synthetic route of 457097-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
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