Sodium borohydride → 4-Hydroxy-3-[2'-(hydroxymethyl)-1,1'-biphenyl-4-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

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Reaction Steps

To a solution of 3-(2′-formyl-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (0.03 g, 0.08 mmol) in MeOH (2 mL) and dichloromethane (0.5 mL) was added NaBH4 (0.012 g, 0.32 mmol) in a single portion. The reaction was stirred at room temperature for 18 h. It was then cooled to 0° C. in an ice bath, quenched by slow addition of 1N HCl (10 mL) and extracted with dichloromethane (3×10 mL). The organic layers were dried with anhydrous sodium sulfate, concentrated and purified by RP-HPLC to give the title compound as a white solid. MS (ESI) m/e 372.9 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 12.42 (br s, 1H), 7.60 (dd, 1H), 7.50 (d, 2H), 7.32–7.42 (m, 4H), 7.26 (dd, 1H), 7.07 (s, 1H), 4.46 (s, 2H).

Provenance & Evidence