1,2-Dichloroethane → 2-(benzyloxy)-5-bromo-N-(pyridin-3-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

3-Pyridinamine (123 mg, 1.30 mmol) in DCM (15 ml) was added to a stirred solution of 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5, method A; 200 mg, 0.65 mmol), HOBT (150 mg, 0.98 mmol) and EDC (187 mg, 0.98 mmol) in DCM (15 ml) under nitrogen at room temperature. The reaction mixture was stirred at 20° C. overnight. The reaction mixture was partitioned between DCM (50 ml) and water (25 ml). The organic phase was washed with saturated brine (25 ml), dried over sodium sulphate and evaporated in vacuo to give the crude product as a yellow solid. The crude product was added to a Biotage column and was eluted with petroleum ether:ethyl acetate (3:1) to yield the title compound as a white solid. 75 mg. MS (electrospray): m/z [M+H]+=383

Provenance & Evidence