A-769662 → HCID 135594051, compound

Participants

Reaction Steps

MeMgBr (1.4 M in ether, 15 mL, 21 mmol) was slowly added to a solution of 4-hydroxy-3-(2′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (1.5 g, 4.18 mmol) in anhydrous THF (90 mL) at 0° C. The reaction mixture was slowly warmed to room temperature over 4 hours and quenched with 1N HCl. It was then filtered, concentrated, and purified on a RP-HPLC system to give the title compound. MS (ESI) m/e 375.0 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 12.37 (br s, 1H), 11.33 (s, 1H), 9.51 (s, 1H), 9.32 (s, 1H), 7.49 (d, J=8.59, 2H), 7.42 (d, J=8.59, 2H), 7.29 (dd, J=7.68, 1.85, 1H), 7.18–7.14 (m, 1H), 6.96 (dd, J=8.29, 1.23, 1H), 6.91–6.84 (m, 1H), 6.75 (s, 1H), 2.55 (s, 3H).

Provenance & Evidence