Sodium Formate → 7-Fluoroquinoline-6-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a suspension of Pd(PPh3)4 (1.27 g, 1.1 mmol) and sodium formate (13.8 g, 132 mmol, 6 eq.) in acetonitrile (30 mL) was added a solution of 6-bromo-7-fluoro quinoline (5 g, 22 mmol) in DMSO (30 mL). The reaction mixture was heated at 120° C. under a CO atmosphere (1 MPa) for 4 h, cooled to it and concentrated under reduced pressure. The residue was partitioned between water (100 mL) and EtOAc (150 mL). The organic layer was separated, washed with brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure to give a residue, which was purified by column chromatography with gradient petroleum:EtOAc from 10:1 to 3:1 to give the title compound as a white solid (400 mg, 10.4%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.95 (s, 1H), 8.46 (m, 1H), 8.20 (m, 1H), 7.75 (d, 1H), 7.53 (m, 1H).

Provenance & Evidence