3-Bromoquinoline → HCID 18187735, compound

Participants

Reaction Steps

A solution of 1-(t-butoxycarbonyl)-4-(prop-2-en-1-yl)piperidine (from Procedure 5, Step B) (260 mg, 1.15 mmol) in THF (3 mL) under argon was treated with 0.5M 9-BBN solution in THF (2.30 mL, 1.15 mmol). The resulting mixture was stirred at rt for 2 h, then treated with sodium methoxide (68 mg, 1.25 mmol). The resulting mixture was stirred until it was homogeneous (˜15 min) and then was treated with 3-(bromo) quinoline (0.155 mL, 1.15 mmol) and [1,1′-bis(triphenylphosphino)ferrocene)dichloropalladium methylene chloride (41 mg, 0.05 mmol). The resulting mixture was heated at reflux for 30 min, cooled and quenched with 1N NaOH (20 mL). The quenched reaction was extracted with 2×50 mL of ether; the extracts were dried over magnesium sulfate, combined and concentrated. FC (15 g of silica gel, 4:1 v/v hexaneslethyl acetate) afforded the title compound (240 mg).

Provenance & Evidence