Dichloromethane → HCID 68836920, compound

Participants

Reaction Steps

To a stirring suspension of methyl 4-aminopyridine-3-carboxylate (0.10 g, 0.659 mmol) in dichloromethane (1 mL) was added a solution of 4-tert-butyl-2-(1-Boc-piperidin-4-yloxy)benzoyl chloride (1.3 mmol) in dichloromethane (6 mL), followed by N,N-diisopropylethylamine (0.15 mL, 0.8 mmol) and 4-N,N-dimethylaminopyridine (0.0084 g, 0.068 mmol). After stirring overnight, the solution was diluted with ethyl acetate and washed three times with satd aq NaHCO3. The combined aq phase was back extracted with ethyl acetate and the combined organic phase was dried with MgSO4, filtered and concentrated in vacuo. The residue was chromatographed over silica gel, eluting with a gradient of 30% ethyl acetate in hexanes through 100% ethyl acetate. The product containing fractions were combined and concentrated in vacuo to give the title compound (0.223 g, 66%) as a thick yellow syrup.

Provenance & Evidence