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

Participants

Reaction Steps

A mixture of tert-butyl (6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-Pyrrolo[3,2-b]pyridin-5-yl)methyl(methyl)carbamate (200 mg, 0.5 mmol) in CH2Cl2 (5 mL) and TFA (0.5 mL) was stirred at RT for 2 h. The reaction mixture was cooled to 0° C. and then quenched by adding a sat'd. aq. NaHCO3 until the pH was about 8. The mixture was extracted with EtOAc (20 mL×2), and the combined extracts dried (MgSO4), filtered and concentrated under reduced pressure to afford 120 mg (70%) of (6-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-N-methylmethanamine as a brown oil. MS (ESI): m/z=310.3 [M+1]+.

Provenance & Evidence