2-Amino-3-bromopyridine → Benzyl 4-[2-[(3-bromopyridin-2-yl)amino]-2-oxoethyl}-3,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

Trimethylaluminum (0.91 g, 12.61 mmol) was added to a solution of benzyl 4-(2-methoxy-2-oxoethyl)-3,6-dihydropyridine-1(2H)-carboxylate (2.43 g, 8.41 mmol) and 3-bromopyridin-2-amine (1.60 g, 9.25 mmol) in dichloroethane (45 mL) at 0° C. The reaction mixture was slowly warmed to 55° C. After 18 h, the reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with dichloromethane (4×). The combined organic extracts were washed with Rochelle's salts (1N in water), saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (50% hexanes/ethyl acetate→100% ethyl acetate) gave the title compound (1.91 g). MS 430.0 (M).

Provenance & Evidence