Category: 206551-41-9

Related Products of 206551-41-9,Some common heterocyclic compound, 206551-41-9, name is Methyl 3-bromo-2-fluorobenzoate, molecular formula is C8H6BrFO2, 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 70 mL pressure vial containing 2-chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)pyridin-3-amine (Step 1 of Example 54, 500 mg, 2.24 mmol), methyl 3-bromo-2-fluorobenzoate (Oakwood, 781 mg, 3.35 mmol) and Cs2CO3 (728 mg, 2.24 mmol) in dioxane (10 mL) was added 1,1?-bis(diphenylphosphino)ferrocene (62.0 mg, 0.11 mmol), Pd(OAc)2 (85 mg, 0.38 mmol) and Xantphos (65 mg, 0.11 mmol). N2 was bubbled through the reaction mixture for 2 min. The vial was sealed and heated to 100° C. for 24 h. BrettPhos precatalyst (100 mg, 0.12 mmol) and additional methyl 3-bromo-2-fluorobenzoate (781 mg, 3.35 mmol) were added. N2 was bubbled through the reaction mixture for 2 min, and then heating was continued at 110° C. for 24 h. Additional BrettPhos precatalyst (100 mg, 012 mmol) was added and stirring was continued at 120° C. for 5 h. BrettPhos precatalyst (100 mg, 0.12 mmol) was again added and the reaction mixture was heated at 120° C. for 5 h. After cooling to room temperature, the mixture was diluted with CHCl3 and filtered through Celite® rinsing with CHCl3. The filtrate was concentrated and purified using ISCO silica gel chromatography (40 g column, gradient from 0percent to 100percent EtOAc/CH2Cl2) to give the title compound (140 mg, 17percent) as a white solid. 1H NMR (400 MHz, CDCl3) delta 7.90 (d, J=2.1 Hz, 1H), 7.74 (ddd, J=8.0, 6.5, 1.7 Hz, 1H), 7.52-7.44 (m, 1H), 7.24 (d, J=0.9 Hz, 1H), 7.17 (t, J=2.0 Hz, 1H), 6.34 (s, 1H), 3.97 (d, J=0.7 Hz, 6H), 2.32 (s, 3H); LCMS (M+H)=376.3; HPLC RT=2.23 min (Column: Chromolith ODS S5 4.6×50 mm; Mobile Phase A: 10:90 MeOH:water with 0.1percent TFA; Mobile Phase B: 90:10 MeOH:water with 0.1percent TFA; Temperature: 40° C.; Gradient: 0-100percent B over 4 min; Flow: 4 mL/min).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-bromo-2-fluorobenzoate, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Norris, Derek J.; Delucca, George V.; Gavai, Ashvinikumar V.; Quesnelle, Claude A.; Gill, Patrice; O’Malley, Daniel; Vaccaro, Wayne; Lee, Francis Y.; DeBenedetto, Mikkel V.; Degnan, Andrew P.; Fang, Haiquan; Hill, Matthew D.; Huang, Hong; Schmitz, William D.; Starrett, JR., John E.; Han, Wen-Ching; Tokarski, John S.; Mandal, Sunil Kumar; (220 pag.)US2016/176864; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 206551-41-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 206551-41-9 name is Methyl 3-bromo-2-fluorobenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 1: Methyl 3-((2-chloro-5-(1 ,4-dimethyl- 1H-1 ,2,3-triazol-5-yl)pyridin-3- yl)amino)-2-fluorobenzoateTo a 70 mL pressure vial containing 2-chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5- yl)pyridin-3-amine (Step 1 of Example 54, 500 mg, 2.24 mmol), methyl 3-bromo-2-fluorobenzoate (Oakwood, 781 mg, 3.35 mmol) and Cs2CO3 (728 mg, 2.24 mmol) in dioxane (10 mL) was added 1,1 ?-bis(diphenylphosphino)ferrocene (62.0 mg, 0.11 mmol), Pd(OAc)2 (85 mg, 0.38 mmol) and Xantphos (65 mg, 0.11 mmol). N2 was bubbled through the reaction mixture for 2 mm. The vial was sealed and heated to 100 °C for 24h. BrettPhos precatalyst (100 mg, 0.12 mmol) and additional methyl 3-bromo-2-fluorobenzoate (781 mg, 3.35 mmol) were added. N2 was bubbled through the reactionmixture for 2 mm, and then heating was continued at 110 °C for 24 h. Additional BrettPhos precatalyst (100 mg, 012 mmol) was added and stirring was continued at 120°C for 5 h. BrettPhos precatalyst (100 mg, 0.12 mmol) was again added and the reaction mixture was heated at 120 °C for 5 h. After cooling to room temperature, the mixturewas diluted with CHC13 and filtered through Celite® rinsing with CHC13. The filtrate was concentrated and purified using ISCO silica gel chromatography (40 g column, gradient from 0percent to 100percent EtOAc/CH2C12) to give the title compound (140 mg, 17percent) as a white solid. ?H NMR (400 MHz, CDC13) oe 7.90 (d, J=2.1 Hz, 1H), 7.74 (ddd, J=8.0, 6.5, 1.7 Hz, 1H), 7.52 – 7.44 (m, 1H), 7.24 (d, J=0.9 Hz, 1H), 7.17 (t, J2.0 Hz, 1H), 6.34 (s, 1H),3.97 (d, J=0.7 Hz, 6H), 2.32 (s, 3H); LCMS (M+H) = 376.3; HPLC RT = 2.23 mm(Column: Chromolith ODS S5 4.6 x 50 mm; Mobile Phase A: 10:90 MeOH:water with0.1percent TFA; Mobile Phase B: 90:10 MeOH :water with 0.1percent TFA; Temperature: 40 °C;Gradient: 0-100percent B over 4 mm; Flow: 4 mL/min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-bromo-2-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 206551-41-9, name is Methyl 3-bromo-2-fluorobenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C8H6BrFO2

In a 500 mL flask was placed 1 ,1-diotamethylethyl carbamate (6 03 g, 51 5 mmol), methyl 3-bromo-2-fluorobenzoate (10 g, 42 9 mmol), Pd2(dba)3 CHCI3 (0 89 g, 0 86 mmol), xantphos (1 49 g, 2 57 mmol) and cesium carbonate (16 8 g, 51 5 mmol) The flask was sealed with a rubber septum, placed under high vac, and toluene (200 mL) was added Three cycles of high vac/N2 were performed and the reaction 25 mixture was stirred at 90 C overnight The reaction was filtered through a pad of celite with EtOAc washing and concentrated To the residue was added DCM (200 mL) followed by TFA (50 mL, 649 mmol), and the mixture was stirred at rt for 1 h The volatiles were removed under reduced pressure and the residue was taken up in EtOAc and washed with saturated NaHCO3 and brine The organic layer was dried over sodium sulfate and stripped onto silica and column chromatographed on silica with 5% to 50% EtOAc Hexane to give 5 53 g (76%) of the title compound of Step B 1H-NMR (400 MHz, DMSO-d6) delta 6 92 – 7 01 (m, 3 H), 5 37 (s, 2 H), and 3 81 (s, 3 H) MS (ESI) 170 [M+H]+

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; GLAXOSMITHKLINE LLC; ADJABENG, George; BAUM, Erich; BIFULCO, Neil; DAVIS-WARD, Ronda, G.; DICKERSON, Scott, Howard; DONALDSON, Kelly, Horne; HORNBERGER, Keith; PETROV, Kimberly; RHEAULT, Tara, Renae; SAMMOND, Douglas, McCord; SCHAAF, Gregory, M.; STELLWAGEN, John; UEHLING, David, Edward; WATERSON, Alex, Gregory; WO2010/104899; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 206551-41-9, These common heterocyclic compound, 206551-41-9, name is Methyl 3-bromo-2-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.

Example 198 3-Bromo-2[-(4-methoxybenzenesulfonyl)amino]-benzoic acid methyl ester To 0.096g (0.5 mmol) of 4-methoxyphenylsulphonamide in 3mL of DMF was added in one portion 0.020g (0.50 mmol) of 60percent sodium hydride and the reaction was stirred at 25-C for 15 min. Then, 0.135g (0.58 mmol) of methyl 3-bromo-2-fluorobenzylate was added to the solution in one portion and the resulting mixture was heated at 90 ¡ãC (bath temperature) for 18h. The reaction was cooled to room temperature, acidified with 1N HCl and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica eluding with 30percent-50percent ethyl acetate/hexane to provide 0.037g (19percent) of the desired product. 1H-NMR(CDCl3): 8 ppm (s, 1H, NH), 6.8-7.8 ppm (m, 7H, Ar), 3.9 ppm (s, 1H, OMe), 3.7 ppm (s, 1H, OMe).

The synthetic route of 206551-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; EP938471; (2001); B1;,
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 206551-41-9 as follows. Application In Synthesis of Methyl 3-bromo-2-fluorobenzoate

Methyl 3-bromo-2-fluorobenzoate (500 mg, 2.15 mmol) dissolved in diethyl ether (15 mL) was cooled to 0 ¡ãC and treated with lithium aluminum hydride (81 mg, 2.13 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 6h. The reaction mixture was againcooled to 0 ¡ãC and methanol was added dropwise slowly followed by water. The reaction mixture wasdiluted with ethyl acetate and washed with water. The organic layer was concentrated to give (3-bromo- 2-fluorophenyl)methanol.

According to the analysis of related databases, 206551-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; APPLEBY, Todd; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; GUERRERO, Juan A.; JABRI, Salman Y.; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; NOTTE, Gregory; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (724 pag.)WO2018/195321; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 206551-41-9, A common heterocyclic compound, 206551-41-9, name is Methyl 3-bromo-2-fluorobenzoate, molecular formula is C8H6BrFO2, 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.

REFERENCE EXAMPLE 83 To a mixture of methyl 3-bromo-2-fluorobenzoate (117 mg), 2-thiopheneboronic acid (83 mg) and 1,2-dimethoxyethane (2 ml) were added a 2M aqueous solution of sodium carbonate (0.83 ml) and tetrakis(triphenylphosphine)palladium(0) (29 mg) at ambient temperature. The mixture was heated for 3 hours at 90¡ã C. After cooling, the reaction mixture was diluted with ethyl acetate (30 ml), and washed with water (20 ml*3) and brine (20 ml). The organic layer was dried over magnesium sulfate and filtered. After evaporation, the residue was chromatographed on a silica gel eluding with a mixture of ethyl acetate and n-hexane to give methyl 2-fluoro-3-(2-thienyl)benzoate (99 mg). Mass: 237 (m/z, (M+H)+) NMR(DMSO-d6, delta): 3.89 (3H, s), 7.1-7.3 (1H, m), 7.39 (1H, t, J=7.8 Hz), 7.6-7.9 (3H, m), 8.0-8.2 (1H, m).

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; Yamada, Akira; Spears, Glen; Hayashida, Hisashi; Tomishima, Masaki; Ito, Kiyotaka; Imanishi, Masashi; US2003/176454; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 206551-41-9, These common heterocyclic compound, 206551-41-9, name is Methyl 3-bromo-2-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.

Step B: Methyl 3-amino-2-fluorobenzoate; In a 500 mL flask was placed 1,1-dimethylethyl carbamate (6.03 g, 51.5 mmol), methyl 3-bromo-2-fluorobenzoate (10 g, 42.9 mmol), Pd2(dba)3.CHCl3 (0.89 g, 0.86 mmol), xantphos (1.49 g, 2.57 mmol) and cesium carbonate (16.8 g, 51.5 mmol). The flask was sealed with a rubber septum, placed under high vacuum, and toluene (200 mL) was added. Three cycles of high vacuum/N2 were performed and the reaction mixture was stirred at 90 C. overnight. The reaction was filtered through a pad of celite with EtOAc washing and concentrated. To the residue was added DCM (200 mL) followed by TFA (50 mL, 649 mmol), and the mixture was stirred at rt for 1 h. The volatiles were removed under reduced pressure and the residue was taken up in EtOAc and washed with saturated NaHCO3 and brine. The organic layer was dried over NaSO4, stripped onto silica and column chromatographed on silica with 5% to 50% EtOAc:Hexane to give 5.53 g (76%) of the title compound of Step B. 1H-NMR (400 MHz, DMSO-d6) delta 6.92-7.01 (m, 3H), 5.37 (s, 2H), and 3.81 (s, 3H). MS (ESI): 170 [M+H]+.

The synthetic route of 206551-41-9 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