Sodium borohydride → 6-(tert-butyl)-2-(3-chloro-2-(hydroxymethyl)phenyl)-8-fluorophthalazin-1(2H)-one

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Reaction Steps

2-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-chloro-benzaldehyde 101i (519 mg, 1.4 mmol) was dissolved in DCM (2 mL) with stirring at room temperature, and then 1 mL of iPA was added to the solution. The resulting solution was cooled to 4° C., and NaBH4 (27 mg, 0.7 mmol) was added in one portion. After 30 min stirring, the reaction was quenched by adding H2O (2 mL). The aqueous layer was extracted with CH2Cl2 (2×5 mL), washed with brine and dried over MgSO4. The filtrate was concentrated to give a residue which was purified by silica gel chromatography eluting with 0-20% EtOAc/CH2Cl2 to furnish 101j as a white solid (385 mg, 72%). MS: [M+H]+: 361

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