Dimethylcarbamoyl Chloride → HCID 86689854, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridine 4-oxide (2.4 g, 7.84 mmol) in 1,2-dichloroethane (60 mL) was added dimethylcarbamic chloride (1.3 g, 11.76 mmol), followed by addition of trimethylsilyl cyanide (1.2 g, 11.76 mmol). The mixture was stirred under nitrogen at 80° C. overnight. The resulting mixture was quenched by addition of a sat'd aq. NaHCO3 solution. The organic layer was washed with H2O (50 mL×3) and concentrated under reduced pressure. The crude product was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (4:1) as eluent to afford 1.1 g (44.5%) of 6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile. MS (ESI) m/z: 316.1 [M+1]+.

Provenance & Evidence