Triethylamine → 3-bromo-N-methoxy-N-methylpicolinamide

Participants

Reaction Steps

To a solution of 3-bromopyridine-2-carboxylic acid (3-1; 250 mg, 1.24 mmole) in CH2Cl2 (5 mL) was added Et3N (0.21 mL, 3.72 mmole) then isobutyl chloroformate (0.19 mL, 1.49 mmole) at 0° C. After 30 minutes N,O-dimethylhydroxylamine hydrochloride (181 mg, 1.86 mmole) was added. After 15 minutes the mixture was warmed to RT. After 18 hr the mixture was diluted with H2O and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column (50% EtOAc/hexanes) gave the title compound (3-2) as a clear oil: 1H-NMR (500 MHz, CDCl3) δ 8.56 (m, 1H), 7.92 (m, 1H), 7.24 (m, 1H), 3.58 (s, 3H), 3.42 (s, 3H).

Provenance & Evidence