Sodium borohydride → 5-(5-fluoro-4-hydroxymethyl-pyridin-3-yl)-3H-isobenzofuran-1-one

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Reaction Steps

To 3-fluoro-5-(1-oxo-1,3-dihydro-isobenzofuran-5-yl)-pyridine-4-carbaldehyde (180 mg, 0.700 mmol) in MeOH (7 mL) at 0° C. was added sodium borohydride (39.7 mg, 1.050 mmol). The reaction mixture was stirred at room temperature for 30 min. The reaction was quenched with water and extracted with DCM twice. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude was dissolved in MeOH (10 mL) and purified on HPLC using RP18 column and gradient 0.1% aqueous NH4OH in acetonitrile to afford 5-(5-fluoro-4-hydroxymethyl-pyridin-3-yl)-3H-isobenzofuran-1-one. 1H NMR (400 MHz, MeOD) δ ppm 4.62 (d, J=1.5 Hz, 2H), 5.51 (s, 2H), 7.78 (d, J=7.8 Hz, 1H), 7.82 (s, 1H), 8.04 (d, J=7.8 Hz, 1H), 8.46 (s, 1H), 8.59 (d, J=1.5 Hz, 1H); HRMS: (ESI) m/z 260.0735 [(M+H)+ Calcd for C14H10FNO3 260.0723].

Provenance & Evidence