Ethanethiol → HCID 53379905, compound

Participants

Reaction Steps

To a solution of 3-(benzyloxy)-5-(biphenyl-3-yl)-4-fluoro-1-methylpyridin-2(1H)-one (22 mg, 0.057 mmol) in CH2Cl2 (0.8 mL) was added ethanethiol (53 mg, 0.856 mmol) followed by BF3.OEt2 (0.108 mL, 0.856 mmol). The resulting mixture was stirred at room temperature for 3.5 h, diluted with MeOH and concentrated. Purification by preparative HPLC (10-80% CH3CN/H2O over 20 min, 0.05% added TFA) afforded 13 mg (77%) of 5-biphenyl-3-yl-4-fluoro-3-hydroxy-1-methylpyridin-2(1H)-one as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.61 (d, J=7.9 Hz, 4H), 7.49 (dt, J=22.1, 7.5 Hz, 3H), 7.42-7.35 (m, 2H), 6.99 (d, J=7.9 Hz, 1H), 6.40 (br, 1H), 3.69 (s, 3H). High resolution mass spec (FT/ICR) calc (M+H)+=296.1081 found 296.1081.

Provenance & Evidence