Sodium borohydride → N-(2,4-difluorophenyl)-8-(hydroxymethyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

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Reaction Steps

To an ice-cooled solution of N-(2,4-difluorophenyl)-8-formyl-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide in ethanol (1 mL) was added sodium borohydride (10 mg, 0.3 mmol, 6 equiv). After 3 hr, excess sodium borohydride was quenched with saturated aqueous ammonium chloride solution (3 mL). The ethanol was removed in vacuo, and the resulting aqueous solution was extracted with ethylacetate (3×3 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (3:2 hexanes/ethylacetate) provided 159bp (5.2 mg, 30%). 1H NMR (500 MHz, CDCl3) δ 7.26 (m, 1 H), 7.15 (m, 1 H), 7.05 (m, 1 H), 6.86-6.93 (m, 4 H,), 5.25 (s, 2 H), 4.55 (d, J=6.7 Hz, 2 H), 4.06 (m, 1 H), 3.40 (s, 3 H). LCMS (ESI) m/z: 388.1.

Provenance & Evidence