Benzyl Alcohol → HCID 16042339, compound

Participants

Reaction Steps

16.8 mg of palladium acetate, 83.2 mg of dppf, 0.418 mL of triethylamine, 767 mg of 1′-[(4,8-dimethoxyquinolin-2-yl)carbonyl]-6-bromospiro[chroman-2,4′-piperidin]-4-one, 0.776 mL of benzyl alcohol and 7.5 mL of DMF were stirred under a carbon monoxide atmosphere at 100° C. for 15 hours. The reaction mixture was diluted with 40 mL of ethyl acetate, and filtered through Celite. The filtrate was washed with water, dried over sodium sulfate, and concentrated. The residue was purified through silica gel chromatography (75% EtOAc/hexane) to obtain the intended compound. 1H-NMR (CDCl3) δ: 8.60 (1H, d, J=2.2 Hz), 8.21 (1H, dd, J=8.8, 2.2 Hz), 7.77 (1H, d, J=8.3 Hz), 7.49-7.31 (6H, m), 7.19 (1H, s), 7.09-7.05 (2H, m), 5.35 (2H, s), 4.62-4.55 (1H, m), 4.24-4.16 (1H, m), 4.08 (3H, s), 4.02 (3H, s), 3.60 (1H, ddd, J=13.1, 11.8, 2.9 Hz), 3.38 (1H, td, J=13.1, 2.9 Hz), 2.85 (1H, d, J=16.6 Hz), 2.79 (1H, d, J=16.6 Hz), 2.24-2.16 (1H, m), 2.10-2.02 (1H, m), 2.00-1.86 (2H, m). MS [M+H]+=567.

Provenance & Evidence