Ethyl 4-piperidinecarboxylate → HCID 23438700, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-fluoropyridine A-5 (0.31 mL, 3.0 mmol) and ethyl piperidine-4-carboxylate (1.39 mL, 9.0 mmol) were dissolved in anhydrous pyridine (2.0 mL) at room temperature under an argon atmosphere, in a 10 mL microwave reactor vial. The reaction mixture was sealed and heated at 190° C. for 60 mins under microwave irradiation, then successively cooled to room temperature, diluted with methylene chloride (60 mL), quenched with a 1 N aqueous solution of hydrogen chloride (40 mL) and decanted. The aqueous layer was extracted with methylene chloride (2×100 mL); the combined extracts were sequentially washed with water (70 mL), brine (70 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The crude residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate gradient) to give ethyl 1-(5-bromopyridin-2-yl)piperidine-4-carboxylate A-14 (935.0 mg, Yield=99%). MS (ESI), [M+1]+ 313, 315.

Provenance & Evidence