Benzyl Alcohol → HCID 58286938, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromo-8-fluoro-3-methyl-2-pyridin-3-yl-2H-isoquinolin-1-one (320 mg, 0.96 mmol) and benzyl alcohol (300 μL, 2.90 mmol) were added to palladium (II) acetate (22 mg, 0.096 mmol) and 4,5-bis-diphenylphosphanyl-9,9-dimethyl-9H-xanthene (56 mg, 0.096 mmol) and sodium carbonate (305 mg, 2.88 mmol) in toluene (3 mL). The reaction mixture was stirred under an atmosphere of carbon monoxide at 100° C. for 2 days. The reaction mixture was poured onto a 25 g silica gel column and it was flash chromatographed (gradient: heptane-ethyl acetate) to give the title compound (151 mg, yield 40.5%). LC-MS (m/z) 389.2 (MH+); tR=1.15. 1H NMR (500 MHz, CDCl3): 1.96 (s, 3H, Me), 5.42 (s, 2H), 7.12 (dd, J=8.3 Hz, J=10.9 Hz, 1H), 7.31 (d, J=8.2 Hz, 1H), 7.35-7.42 (m, 3H), 7.43-7.5 (m, 3H), 7.55-7.63 (m, 2H), 8.5 (d, J=2.1 Hz, 1H), 8.71 (dd, J=4.7 Hz, J=1 Hz, 1H).

Provenance & Evidence