Pyridine → Methyl 1-(4-formyl-2-(5-methylisoxazole-3-carboxamido)phenyl)piperidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 1-(2-amino-4-formylphenyl)piperidine-4-carboxylate 59 (0.488 g, 1.9 mmol) in DCM (10 mL) at 0° C. was added pyridine (0.300 mL, 3.7 mmol) and 5-methylisoxazole-3-carbonyl chloride (0.185 g, 1.3 mmol). The reaction mixture was stirred at 0° C. for 30 min, additional acid chloride (88 mg) was added and stirring was continued at 0° C. After 30 min, the reaction mixture was diluted with EtOAc, washed with saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 20% to 50% EtOAc in hexanes) gave methyl 1-(4-formyl-2-(5-methylisoxazole-3-carboxamido)phenyl)piperidine-4-carboxylate 60 (0.268 g, 39% yield) as a pale yellow solid. Mass spectrum: calculated for C19H21N3O5 371.2. found 372.2 (M++1).

Provenance & Evidence