Analyzing the synthesis route of 5-Bromo-2-methoxynicotinic acid

According to the analysis of related databases, 54916-66-4, the application of this compound in the production field has become more and more popular.

Electric Literature of 54916-66-4, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

As shown in step 4(b)-i of Scheme 4(b), HATU (8.194 g, 2.55 mmol) and DIPEA (5.570g, 7.507 mL, 43.10 mmol) was added to a solution of 5-bromo-2-methoxypyridine-3- carboxylic acid (5 g, 21.55 mmol) in DMF (50 mL). The resulting solution was stirred for 10 minutes followed by the addition of ethanamine hydrochloric acid (1.757 g, 2.196 mL, 21.55 mmol). The resulting solution was stirred at room temperature for 5 hours. To the reaction mixture was added water (100 mL) and ethyl acetate (100 mL). The organic layer was separated and dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (0-2% methanol in dichloromethane gradient) to produce 5-bromo-N-ethyl-2-methoxynicotinamide as off white solid (Compound 2015, 3.4g): 1H NMR (DMSO-d6) delta 8.41 (d, J = 2.5 Hz, 1H), 8.31 (s, 1H), 8.20-8.13 (m, 1H), 3.95 (s, 3H), 3.35-3.23 (m, 2H), 1.11 (t, J = 7.2 Hz, 3H).

According to the analysis of related databases, 54916-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; ARONOV, Alex; COME, Jon, H.; DAVIES, Robert, J.; PIERCE, Albert, C.; WANG, Jian; NANTHAKUMAR, Suganthini; CAO, Jingrong; BANDARAGE, Upul, K.; KRUEGER, Elaine; TIRAN, Amaud, Le; LIAO, Yusheng; MESSERSMITH, David; COLLIER, Philip, N.; GREY, Ronald; O’DOWD, Hardwin; HENDERSON, James, A.; GRILLOT, Anne-Laure; WO2011/87776; (2011); A1;,
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