Sodium borohydride → 1-[4-Chloro-5-(2-hydroxyethyl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol

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Reaction Steps

To a room temperature solution of (4-chloro-7-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[3,2-d]pyrimidin-5-yl)acetaldehyde (91 mg, 0.18 mmol) in 3 mL of THF was added NaBH4 (4 mg, 0.09 mmol, 0.5 equiv.). After 2 hours, the reaction was quenched with water and extracted with EtOAc. The organics were dried, filtered, and concentrated in vacuo. The residue was purified by HPLC (5-95% CH3CN/water 0.1% TFA). The desired peaks were combined, made basic with saturated aqueous sodium bicarbonate, and concentrated to remove excess CH3CN. The resulting aqueous layer was then extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo to provide 48 mg (53%) of the title compound as a white solid. MS m/z 506.34 (MH+).

Provenance & Evidence