Category: 128071-79-4

Electric Literature of 128071-79-4 ,Some common heterocyclic compound, 128071-79-4, molecular formula is C6H5BrFN, 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 sealable reaction flask containing a solution of Intermediate 15E (9.90 g,33.7 mmol) in Dioxane (195 mL) was added 4-bromo-2-fiuoro-3-methvlpyridine (6.21 g, 32.7 mmoi), Water (65.0 mL) and Na2CO3 (13.86 g, 131 inmol). After the mixture was degassed with Argon for 10-15mm, Pd(Ph3P)4 (1.888 g, 1634 mmoi) was added, the flask was sealed and the mixture was heated to 100 C for 24 hours, then allowed to slowly cool to rt. Reaction was diluted with EtOAc and water, plus sonication to break up solids, then transferred to a sep funnel. The layers were separated and the aqueous layer was extracted once more with EtOAc. The organic layers were combined, washed with brine, dried over anhyd Na2SO4, filtered and concentrated in vacuo to afford a dark brown residue. Purified on silica gel colunm chromatography to give Intermediate 23A (7.23 g, 26.1 minol, 80% yield). LC-MS Anal. Calc?d for CI6H20FNO2 277.15, found [M+Hj 278.2, Tr = 104 mm (Method A).

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. 128071-79-4, 4-Bromo-2-fluoro-3-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHERNEY, Emily Charlotte; SHAN, Weifang; ZHANG, Liping; NARA, Susheel Jethanand; HUANG, Audris; BALOG, James Aaron; (129 pag.)WO2018/39512; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 128071-79-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.128071-79-4, name is 4-Bromo-2-fluoro-3-methylpyridine, molecular formula is C6H5BrFN, molecular weight is 190.013, as common compound, the synthetic route is as follows.

A mixture of 4-bromo-2-fluoro-3-picoline (1.90 g, 10 mmol, 1.0 eq), pyrazole (1.36 g, 20 mmol, 2.0 eq) and potassium carbonate (2.80 g, 20 mmol, 2.0 eq) in DMSO (20 mL, 0.5 M) was stirred at 70 C. After 16 h, the reaction mixture was added to brine and extracted with EtOAc (3x). The combined extracts were washed with brine, dried (MgS04), filtered and concentrated. The crude material was purified using chromatography on silica gel (0-50% EtO Ac/hexanes) to provide the title compound as a white crystalline solid (2.23 g, 94%). NMR (400 MHz, CDCl3) d 8.12 (d, J= 5.1 Hz, 1H), 8.09 (d, J= 2.2 Hz, 1H), 7.75 (d, J= 1.3 Hz, 1H), 7.51 (d, j= 5.2 Hz, 1H), 6.45 (dd, j= 2.3, 1.9 Hz, 1H), 2.56 (s, 3H). ES-MS [M+H]+ = 238.3.

The chemical industry reduces the impact on the environment during synthesis 128071-79-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig W.; CONN, P. Jeffrey; ENGERS, Darren W.; ENGERS, Julie L.; BENDER, Aaron M.; LONG, Madeline; (120 pag.)WO2019/241467; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 128071-79-4, 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. 128071-79-4, name is 4-Bromo-2-fluoro-3-methylpyridine. A new synthetic method of this compound is introduced below.

To a reaction flask containing a solution of ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)cyclohex-3-en-l-yl)acetate (5.93 g, 20.17 mmol) in Dioxane (120 mL) were added 4-bromo-2-fluoro-3-methylpyridine (3.72 g, 19.58 mmol), Water (40.0 mL) and Na2C03 (8.30 g, 78 mmol). After the mixture was degassed with Ar for 10 min, Pd(Ph3P)4 (1.131 g, 0.979 mmol) was added. The flask was sealed and the mixture was heated to 100 C over night. The reaction mixture was cooled down and diluted with EtOAc and water, plus sonication to break up solids, then transferred to a separation funnel. The layers were separated and the aqueous layer was extracted once more with EtOAc. The organic layers were combined, washed with brine, dried over anhyd Na2S04, filtered and concentrated in vacuo to afford a white precipitate in a pale gold residue. The extract was purified via silica gel flash column chromatography, eluting with 0-25% ethyl acetate in hexane to give (0534) Intermediate 27B (gold pale oil, 5.01 g, 17.72 mmol, 91% yield). LC-MS Anal. Calc’d for C16H20FNO2 277.15, found [M+H] 278.1. Tr = 1.02 min (Method A). NMR (400MHz, chloroform-d) delta 7.94 (d, J=5.0 Hz, 1H), 6.89 (dd, J=5.1, 0.9 Hz, 1H), 5.79 – 5.49 (m, 1H), 4.18 (q, J=7.1 Hz, 2H), 2.55 – 2.28 (m, 4H), 2.26 – 2.11 (m, 5H), 2.00 – 1.86 (m, 2H), 1.55 – 1.41 (m, 1H), 1.29 (t, J=7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,128071-79-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; ZHANG, Liping; HUANG, Audris; SHAN, Weifang; WILLIAMS, David K.; ZHU, Xiao; GUO, Weiwei; (213 pag.)WO2018/209049; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 128071-79-4, 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. 128071-79-4, name is 4-Bromo-2-fluoro-3-methylpyridine. A new synthetic method of this compound is introduced below.

To a reaction flask containing a solution of ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)cyclohex-3-en-l-yl)acetate (5.93 g, 20.17 mmol) in Dioxane (120 mL) were added 4-bromo-2-fluoro-3-methylpyridine (3.72 g, 19.58 mmol), Water (40.0 mL) and Na2C03 (8.30 g, 78 mmol). After the mixture was degassed with Ar for 10 min, Pd(Ph3P)4 (1.131 g, 0.979 mmol) was added. The flask was sealed and the mixture was heated to 100 C over night. The reaction mixture was cooled down and diluted with EtOAc and water, plus sonication to break up solids, then transferred to a separation funnel. The layers were separated and the aqueous layer was extracted once more with EtOAc. The organic layers were combined, washed with brine, dried over anhyd Na2S04, filtered and concentrated in vacuo to afford a white precipitate in a pale gold residue. The extract was purified via silica gel flash column chromatography, eluting with 0-25% ethyl acetate in hexane to give (0534) Intermediate 27B (gold pale oil, 5.01 g, 17.72 mmol, 91% yield). LC-MS Anal. Calc’d for C16H20FNO2 277.15, found [M+H] 278.1. Tr = 1.02 min (Method A). NMR (400MHz, chloroform-d) delta 7.94 (d, J=5.0 Hz, 1H), 6.89 (dd, J=5.1, 0.9 Hz, 1H), 5.79 – 5.49 (m, 1H), 4.18 (q, J=7.1 Hz, 2H), 2.55 – 2.28 (m, 4H), 2.26 – 2.11 (m, 5H), 2.00 – 1.86 (m, 2H), 1.55 – 1.41 (m, 1H), 1.29 (t, J=7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,128071-79-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; ZHANG, Liping; HUANG, Audris; SHAN, Weifang; WILLIAMS, David K.; ZHU, Xiao; GUO, Weiwei; (213 pag.)WO2018/209049; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem