Pyridine → Ethyl 3-(((benzyloxy)carbonyl)amino)-7-bromoquinoline-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

Pyridine (727.5 mg, 9.197 mmol) was added to a solution of ethyl 3-amino-7-bromoquinoline-2-carboxylate (Ark Pharm, 1069 mg, 3.622 mmol) in DCM (10.0 mL). The mixture was cooled to −10° C. A solution of benzyl chloroformate (816.5 mg, 4.547 mmol) in DCM (5.0 mL) was added slowly to the solution. The reaction mixture was allowed to warm to room temperature. After stirring at room temperature for 1 h, the reaction mixture was diluted with EtOAc (100 mL), washed with a saturated aqueous solution of NaHCO3 (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by flash chromatography on silica gel (0-50% EtOAc in hexanes) to give the sub-title compound as an off-white solid (1.54 g, 99%). LCMS calc. for C20H18BrN2O4(M+H)+: m/z=429.0. found 429.0.

Provenance & Evidence