Methyl iodide → tert-butyl (6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)methyl(methyl)carbamate

Participants

Reaction Steps

To a mixture of tert-butyl (6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)methylcarbamate (300 mg, 0.75 mmol) in THF (5 mL) was added NaH (60% dispersion in mineral oil, 110 mg, 2.25 mmol). After stirring at RT for 30 min, CH3I (320 mg, 2.25 mmol) was added, followed by stirring at RT for 3 h. The reaction mixture was quenched by adding a sat'd. aq.solution of NH4Cl and extracted with EtOAc (30 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 to 1:1) to afford 200 mg (66.6%) of tert-butyl (6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)methyl(methyl)carbamate as a brown oil. MS (ESI): m/z=410.3 [M+1]+.

Provenance & Evidence