Diisobutylaluminum hydride → HCID 18187305, compound

Participants

Reaction Steps

Method LLL To a stirred solution of 7-chloro-5-cyano-5-(difluoromethyl)-5,10-dihydrobenzo[b][1,8]naphthyridine (92) (747 mg, 2.55 mmol) in anhydrous methylene chloride (40 mL) at −78° C. was added DIBAL (1.0 M in CH2Cl2, 7.67 mL) dropwise. After 3 h at −50° C., the reaction was quenched with 1.0 N HCl (40 mL), and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Flash chromatography (SiO2, 30% EtOAc-hexane) furnished 93 (299 mg, 39% yield) as a yellow solid.

Provenance & Evidence