3-Bromoquinoline → (5-Oxo-5-quinolin-3-yl-pentyl)-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a stirred solution of 3-bromoquinoline (25 g, 120 mmol) in diethyl ether −78° C. was added nBuLi (2.5M THF, 48 ml, 120 mmol) dropwise over 30 minutes. After 30 minutes, 21-2 (3.9 g, 15 mmol), dissolved in 50 ml ether was added dropwise over 10 minutes. After 30 minutes, the cooling bath was removed. After 1.0 hour, the reaction was quenched with sat. NH4Cl. The organic portion was separated, washed with brine, dried (MgSO4) and concentrated. The residue was chromatographed (silica gel, 20-50% ethyl acetate/hexanes) to give 21-3 as a yellow solid.

Provenance & Evidence