Category: esters-buliding-blocks

Reference of 878207-28-4, These common heterocyclic compound, 878207-28-4, name is Methyl 2-bromo-4,5-difluorobenzoate, 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.

Methyl 4-(5-(benzyloxy)-1H-indol-1-yl)-2-bromo-5-fluorobenzoate [0220] A mixture of 5-benzyloxy indole (11.2g, 0.05 mmol), methyl 2-bromo-4,5-difluoro-benzoate (12.6g, 0.05 mol) and Cs2C03 (24.4g, 0.075 mol) in DMF (150 mL) was stirred at 100 C under N2 atmosphere overnight. The mixture was cooled to room temperature and then filtrated. The filtrate was poured into 150 mL water. A gradual formation of a cream-colored precipitate was observed. Filtration gave the desired intermediate product as a cream-colored solid which is pure enough for further reaction (Yield: 17g, 74.8%). 1HNMR (500 MHz, DMSO-d6) delta: 8.02 (d, J=7 Hz, IH), 7.98 (d, J=l lHz, IH), 7.60 (s, IH), 7.48 (d, J=7.5 Hz, 2H), 7.39 (t, J=7.5 Hz, 2H), 7.32 (t, J=7 Hz, IH), 7.26 (d, J=8.5 Hz, 2H), 6.96 (d, J=8.5 Hz, IH), 6.68 (s, IH), 5.14 (s, 2H) and 3.91 (s, 3H) ppm.

Statistics shows that Methyl 2-bromo-4,5-difluorobenzoate is playing an increasingly important role. we look forward to future research findings about 878207-28-4.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; ZHANG, Yong-kang; ZHOU, Huchen; DING, Charles; PLATTNER, Jacob, J.; FREUND, Yvonne; WO2011/63293; (2011); 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. 4606-07-9, name is Ethyl cyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl cyclopropanecarboxylate

Example 2: Preparation of 2-bromo-1-cyclopropyl-2-(2-fluorophenyl) ethanone: Tetrahydrofuran (90 mL), magnesium turnings (4.4 g), and iodine are charged into a round bottom flask under nitrogen atmosphere at 28C. A solution of 2-bromopropane (22.07 g) in tetrahydrofuran (60 mL) is added to the reaction mass at 20C in 30 minutes and stirred at the same temperature for 1 hour. The solution of 2-(2-fluoro phenyl)acetic acid (11 g) [having less than 0.06% of 2-(3- fluorophenyl)acetic acid impurity] in tetrahydrofuran (20 mL) is added to the reaction mass at 20C in 30 minutes. The reaction mass is heated to 65C and stirred at the same temperature for 3 hours. The reaction mass is cooled to 5C. Ethyl cyciopropanecarboxylate (7.8 g) is added to the reaction mass in 10 minutes at 5C. The reaction mass is heated to 70C and stirred at the same temperature for 3 hours. The reaction mass is cooled to 20C. Water (10 mL) and 2N hydrochloric acid (90 mL) are added to the reaction mass at 20C and stirred for 20 minutes. The organic and aqueous layers are separated. The aqueous layer is extracted with dichloromethane twice (10 mL x 2). The combined organic layer is washed with saturated solution of sodium bicarbonate. The organic layer is dried over sodium sulfate. The solvent is evaporated under vacuum at 40C to get residue (6.8 g). Chloroform (130 ml) is added to the residue at 28C. N- bromo succinamide (7.8 g), azobisisobutyronitrile (0.39 g) and p-toluenesulfonic acid (0.19 g) are added to the reaction mass at 28 C. The reaction mass is heated to 65C and stirred at the same temperature for 4 hours. The reaction mass is cooled to 5C and stirred at the same temperature for 1 hour. The reaction mass is filtered at 5C to remove unwanted residue if any. The filtrate is washed with aqueous solution of sodium bisulfate (50 mL). The organic and aqueous layers are separated. The aqueous layer is extracted with chloroform (10 mL). The organic layers are combined and evaporated at 65C to get residue. Yield: 18.2 g; 2-bromo-1-cyclopropyl-2-(3-fluorophenyl)ethanone impurity. 0.051% by HPLC.

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 4606-07-9.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; ANUMULA, Raghupathi Reddy; GILLA, Goverdhan; AALLA, Sampath; METIL, Dattatray, Shamrao; KURELLA, Srinivas; CHARAGONDLA, Kavitha; WO2012/18791; (2012); A2;,
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Synthetic Route of 26759-46-6, 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. 26759-46-6, name is Methyl 2-amino-4,5-dimethoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a 100 mL three-necked flask were added 1.5 g (6.2 mmol) of methyl 6-amino-3,4_-dimethoxybenzoate, 3 mL (75.5 mmol) of formamide, 3 mL (32.77 mmol) Oxygen Phosphorus and 25 mL of toluene were mixed and heated to reflux. TLC was carried out for 5 h and the reaction was completed. The mixture was taken out to obtain a brown solid. After adding water, the pH value was neutralized with ammonia water. A precipitate of yellowish brown color was precipitated. : EpsilonAlpha = 5: 1, V / V) to obtain a white flocculent solid 1.2 g, yield 78.7%, mp: 184-1860C.

The synthetic route of Methyl 2-amino-4,5-dimethoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guizhou University; Yang Song; Zhang Dongyang; Hu Deyu; Xue Wei; Chen Ling; Liu Bin; Zhou Lei; Li Zhenxing; Wu Zhibing; (20 pag.)CN105037279; (2017); B;,
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These common heterocyclic compound, 35005-25-5, name is Isopropyl 3-aminobenzoate, 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. Formula: C10H13NO2

General procedure: To a suspension of carboxylic acid (100mg) and DMAP (6 eq) in DCM (0.2 M) under nitrogen at -15C was added T3P (3 eq)dropwise over a period of 20 min. The resulting mixture was stirred at -15Cuntil a solution was obtained (2h) and the aniline (3 eq) was added dropwise.The reaction mixture was stirred at -15 C for 1h, slowly warmed to roomtemperature and stirred overnight. Saturated aq. NaHCO3 was thenadded and the aqueous layer extracted with EtOAc. The organic phase was washedwith saturated aq. NH4Cl (x 2), NaHCO3 and brine, driedover Na2SO4, filtered and concentrated under vacuum. Theresidue was dissolved in DCM and purified by flash chromatography (DCM/MeOH97/3 to 92/8).

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

Reference:
Article; Boland, Sandro; Bourin, Arnaud; Alen, Jo; Geraets, Jacques; Schroeders, Pieter; Castermans, Karolien; Kindt, Nele; Boumans, Nicki; Panitti, Laura; Vanormelingen, Jessica; Fransen, Silke; Van De Velde, Sarah; Defert, Olivier; Bioorganic and Medicinal Chemistry Letters; vol. 25; 18; (2015); p. 4005 – 4010;,
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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. 5445-17-0, name is Methyl 2-bromopropanoate, A new synthetic method of this compound is introduced below., Computed Properties of C4H7BrO2

To a suspension of K2CO3 (3.6 g, 26.5 mmol) and tert- butyl piperazine-1-carboxylate (1.0 g, 5.3 mmol) in CH3CN (15 mL) was added methyl 2- bromopropanoate (2.2 g, 13.4 mmol). The reaction was stirred at 80 C for 10 hours. TLC showed that the reaction was complete. The reaction mixture was allowed to cool to room temperature, then the solid filtered off and solvent removed under vacuum. The residue was purified by silica gel column chromatography (CH2Cl2/MeOH = 50:1) to give tert-butyl 4-(1-methoxy-1-oxopropan-2-yl)piperazine-1- carboxylate (2-2) as a brown oil (1.4 g, yield: 99%).

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; KURA ONCOLOGY, INC.; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WU, Tao; LI, Liansheng; WANG, Yi; REN, Pingda; GREMBECKA, Jolanta; CIERPICKI, Tomasz; KLOSSOWSKI, Szymon; POLLOCK, Jonathan; BORKIN, Dmitry; (198 pag.)WO2017/161028; (2017); A1;,
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Synthetic Route of 148547-19-7, 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. 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of methyl 4-bromo-3-methylbenzoate (ABCR, 5 g, 21.8 mmol) in dry 1 ,4- dioxane(100 ml_), were added dry Cs2CO3 (10.65 g, 32.7 mmol) and piperidine (2.2 g, 26 mmol). The mixture was degassed with N2 for 10 min. BINAP (0.67 g, 1.1 mmol) and palladium(ll)acetate (0.24 g, 1.1 mmol) were added under N2 and the resulting mixutre was refluxed for 15h. The reaction mixture was filtered through a pad of celite and the filtrate was evaporated. The crude product was purified by flash chromatography, affording the title product as a off-white solid (4.9 g, 96%). 1H NMR (CDCI3, 400 MHz) delta 7.82-7.84 (m, 2H), 6.97-6.99 (d, 1 H), 3.92 (s, 3H), 2.90-2.93 (m, 4H), 1.67-1.76 (m, 4H), 1.62-1 .63 (m, 2H). LC/MS (Method A): 233.9 (M+H)+. HPLC (Method B) Rt 4.18 min (Purity: 95.4%).

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

Reference:
Patent; MERCK SERONO S.A.; WO2009/43889; (2009); A2;,
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Adding a certain compound to certain chemical reactions, such as: 6290-49-9, name is Methyl 2-methoxyacetate, 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 6290-49-9, Safety of Methyl 2-methoxyacetate

3,5-Difluoropyridine (5.0 g, 43.45 mmol) in THF was cooled to -720C (external -8O0C). LDA (23.9 mL, 1.1 eq.) was added drop-wise so that the internal temp did not increase more than 30C during addition. The reaction mixture turned into a deep brownish, thick phase and was stirred for 30 minutes at this temperature. TMS-Cl (43.4 mL, 43.45 mmol) was added drop-wise in a relatively fast fashion. The reaction became a clear and light yellow solution. LDA (23.9 mL, 1.1 eq.) was added drop-wise in a quicker version, and the reaction mixture was allowed to stir for 2h. Methyl 2-methoxyacetate (5.59 mL, 56.48 mmol) was added quickly through a syringe. The reaction mixture was quenched at -780C by adding 20 ml of saturated NH4Cl solution. Evaporation of the organic extracts under reduced pressure gave a colored residue. Purification utilizing ISCO (0-25% EtOAc/hexanes), gave the title compound (3 g). LCMS: 188 [M+H]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 2-methoxyacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; ALMEIDA, Lynsie; CHUAQUI, Claudio, Edmundo; GUAN, Amy; IOANNIDIS, Stephanos; LAMB, Michelle; PENG, Bo; SU, Qibin; WO2010/20810; (2010); A1;,
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Synthetic Route of 58656-98-7, These common heterocyclic compound, 58656-98-7, name is tert-Butyl 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.

N,N-Dimethyl-3-oxo-1,2-dihydroindazole-5-carboxamide (900 mg; 4.39 mmol; 1.00 eq.), 1-methyl-2-pyrrolidinone (5.00 mL), cesium carbonate (4.29 g; 13.16 mmol; 3.00 eq.) andtert-butyl 4-fluoro-benzoate (2.58 g; 13.2 mmol; 3.00 eq.) were stirred at 110 C for4 hours. The reaction mixture was cooled, diluted with 50 mL of ethyl acetate. The organic layer was washed with brine (20 mL), water ( 20 mL), dried over MgSO4and concentrated.tert-Butyl 4-(5-(dimethylcarbamoyl)-3-oxo-2,3-dihydro-1H-indazol-1-yl)benzoate is isolated without further purification as a beige solid (900 mg; 53.8%)1H NMR (DMSO-d6) delta: 1.58 (s, 9H), 3.01 (s, 6H), 7.58 (dd,J =8.8, 1.7 Hz, 1H), 7.90 – 7.84 (m, 3H), 7.95 (d,J =8.8 Hz, 1H), 8.08 – 8.03 (m, 2H), 11.77 (s, 1H).MS-ESIm/z382 [MH+].

Statistics shows that tert-Butyl 4-fluorobenzoate is playing an increasingly important role. we look forward to future research findings about 58656-98-7.

Reference:
Article; Ouvry, Gilles; Bouix-Peter, Claire; Ciesielski, Fabrice; Chantalat, Laurent; Christin, Olivier; Comino, Catherine; Duvert, Denis; Feret, Christophe; Harris, Craig S.; Lamy, Laurent; Luzy, Anne-Pascale; Musicki, Branislav; Orfila, Danielle; Pascau, Jonathan; Parnet, Veronique; Perrin, Agnes; Pierre, Romain; Polge, Gaelle; Raffin, Catherine; Rival, Yves; Taquet, Nathalie; Thoreau, Etienne; Hennequin, Laurent F.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5802 – 5808;,
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Related Products of 653-92-9, 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. 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Step 1 : Triethylamine (13 mL, 9.44 g, 93.3 mmol), potassium isopropenyltrifluoroborate (18.0 g, 121 .6 mmol) and PdCl2(dppf).CH2Cl2 (1.38 g, 1.70 mmol) were added to a solution of compound 479 (21.8 g, 93.6 mmol) in n-propanol (640 mL) and the mixture was heated at reflux for 17 hours. TLC analysis (10% 2-butanone in heptane) showed starting material remaining and PdCl2(dppf).CH2Cl2 (0.69 g, 0.84 mmol) was added and heating continued for a further 4 hours. After cooling to room temperature the mixture was concentrated to -100 mL in vacuo and diluted with EtOAc (400 mL) before being washed with 1 M HCI (250 mL) and brine (250 mL). The combined aqueous washings were extracted with EtOAc (100 mL) and this was washed with brine (75 mL). The combined organic layers were dried (MgS04) and concentrated in vacuo to give a dark brown oil. Purification by column chromatography (1500 mL silica, 4% EtOAc in heptane) gave the desired product (8.63 g, 47%) as a colorless liquid, contaminated with methyl 4-fluorobenzoate (<10%), and a mixture of the desired product and starting material (5.05 g) also contaminated with methyl 4-fluorobenzoate. Further purification by column chromatography (500 mL silica, 4% EtOAc in heptane) gave a further 1.60 g (9%) of the desired product contaminated with methyl 4-fluorobenzoate (<10%). The product was further purified by Kugelrohr distillation, discarding the forerun (70C, 4 mmHg), and then increasing the temperature to 95C to collect the compound 480 (95% recovery) containing <5% methyl 4- fluorobenzoate. 1 H NMR (400 MHz, CDCI3) delta 7.84 (dd, J = 8.7, 5.9 Hz, 1 H) 6.99 (ddd, J = 8.6, 8.0, 2.6 Hz, 1 H) 6.93 (dd, J = 9.4, 2.6 Hz, 1 H) 5.12 (p, J = 1.6 Hz, 1 H) 4.85 (dq, J = 1.8, 0.9 Hz, 1 H) 3.85 (s, 3H) 2.07 (t, J = 1 .2 Hz, 3H). LCMS m/z 195 [M+H]+. The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-4-fluorobenzoate. I believe this compound will play a more active role in future production and life. Reference:
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); A1;,
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Application of 1687-29-2, These common heterocyclic compound, 1687-29-2, name is Cis-dimethyl cyclohexane-1,2-dicarboxylate, 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.

SOCl2 (15.45 g, 129.8 mmol) was added to a mixture of cis-1,2-cyclohexanedicarboxylic anhydride (200 g, 1298 mmol) and methanol (1400 mL) at 20 °C.There ac-tion mass was refluxed for 3?4 h. Methanol was concentrated completely, the residue was diluted with methyl-tert-butyl ether(MTBE, 1000 mL), sodium bicarbonate solution was added to it. The organic layer was separated and washed with water and brine solution. The organic layer was distilled completely to furnish 8. The residue was dissolved in fresh methanol (1040 mL), and sodium methoxide (28 g, 519.4 mmol) was added. The reaction mass was refluxed for 4h, and methanol was distilled completely under reduced pressure. To the residue, 13percent aqueous NaOH solution (2000 mL)was added. Reaction mass was maintained for 3?4 h at 75 °C and cooled to 0?5 °C. The reaction mass pH was adjusted to 2.0 at 0?5 °C with concentrated HCl (900 mL). The obtained solid was filtered and the wet cake was washed with excess water (1500 mL) and dried under reduced pressure to give a white solid. Yield: 87percent. HRMS (ESI TOFMS): calcd. for C8H12O4Na, 173.0814; found, 173.0821. HPLC conditions: chemical column: Zorbax SB CN (150×4.6 mm)×(3.5mu); mobile phase: A: 0.1percent H3PO4 in H2O/MP; B: ACN, purity by HPLC (area under curve): 94.3percent; (trans) retention time: 6.98 and 2.1percent; (cis) retention time: 7.579. Chiral column: Chiral PAK IC (250×4.6 mm) 5.0 mum; mobile phase: n-hexane/IPA/TFA (950:50 l:1); diluent: methanol/MP (1:1); flow rate: 1.0 mL/min; column temperature: 25 °C; inj. vol.: 10 mul. Wave length: 210 nm. Purity by HPLC (area under curve) 40.35percent (R,S isomer), retention time 16.065; and 56.18percent (R,S isomer) retention time 20.269.

The synthetic route of 1687-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ravi Ganesh; Pachore, Sharad S.; Pratap; Umesh; Basaveswara Rao; Murthy; Suresh Babu; Synthetic Communications; vol. 45; 23; (2015); p. 2676 – 2682;,
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