Sodium hydride → HCID 86762616, compound

Participants

Reaction Steps

To a solution of 6-fluoro-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile (758 mg, 4.71 mmol) in THF (20 mL) was added NaH (60% in mineral oil, 452 mg, 9.42 mmol). After stirring for 30 min, SEM-Cl (1527 mg, 9.42 mmol) was added, followed by stirring at RT for 16 h. The reaction mixture was quenched by adding sat'd aq.NH4Cl and extracted with EtOAc (100 mL×2). The combined extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with a petroleum ether:EtOAc gradient (10:1-0:10) to afford 1096 mg (80%) of 6-fluoro-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile. MS (ESI): m/z=292.1[M+1]+.

Provenance & Evidence