Benzylamine → 2-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

Participants

Reaction Steps

To a solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid (3.00 g, 13.5 mmol) in methylene chloride (20 mL) was added benzyl amine (1.60 mL, 14.9 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent, 6.57 g, 14.86 mmol) and N,N-diisopropylethylamine (4.71 mL; 27.02 mmol) and the mixture was stirred under nitrogen at room temperature for 16 hr. The reaction mixture was diluted with methylene chloride (100 mL), washed with water (100 mL) and brine (2×100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (hexanes:ethyl acetate, 1:1) to provide 2-bromo-4-methyl-thiazole-5-carboxylic acid benzyl amide (3.50 g, 83% yield) as a yelloW solid. 1H NMR (400 MHz, CDCl3) δ 7.47-7.55 (m, 5H), 6.25 (bs, 1H), 4.75 (d, J=8.0 Hz, 2H), 2.79 (s, 3H); MS (M+H)+=312.1; Rt=1.31 min.

Provenance & Evidence