Dimethylformamide → N-(4,6-dichloropyridin-3-yl)-N2-(3-methylbutyl)alaninamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-bromo-N-(4,6-dichloropyridin-3-yl)propanamide (500 mg, 1.68 mmol) in DMF (4 mL) was added potassium carbonate (465 mg, 3.36 mmol) and isoamylamine (4, 0.512 mg, 5.88 mmol), the reaction mixture was then heated to 80° C. and stirred at the same temperature for 2 h. The reaction mixture was then cooled to rt, diluted with water (20 mL) and extracted with ethyl acetate (25 mL×3). The combined organic phases were washed with water, dried over Na2SO4 and evaporated to give a crude residue, which was purified by silica gel column chromatography (eluent: 25% ethyl acetate in hexane) to give desired product (Yield: 69%). 1HNMR (CDCl3, 300 MHz) δ 0.91-0.98 (m, 6H), 1.39-1.43 (m, 3H), 1.60-1.75 (m, 2H), 2.59-2.76 (m, 2H), 3.22-3.31 (m, 2H), 7.41 (s, 1H), 9.51 (s, 1H), 10.20 (br s, 1H).

Provenance & Evidence