Isoquinoline, 1-chloro- → HCID 117661179, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-chloroisoquinoline (5.00 g, 30.6 mmol) and tert-butyl (3R)-3-aminopiperidine-1-carboxylate (7.34 g, 36.6 mmol) in anhydrous toluene (150 mL) was added t-BuOK (10.27 g, 91.7 mmol), BINAP (951 mg, 1.53 mmol), and Pd(OAc)2 (343 mg, 1.53 mmol). The reaction mixture was purged with nitrogen three times, and heated at 110° C. overnight. The reaction mixture was cooled to room temperature and poured into water. The mixture was then extracted with EtOAc (4×150 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting dark solid was purified by silica gel column chromatography eluting with a gradient of (10-15%) EtOAc/petroleum ether to deliver the title compound (4.89 g, 49%) as a yellow solid.

Provenance & Evidence