Dimethylcarbamoyl Chloride → HCID 86689847, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridine-4-oxide (8.75 g, 27.12 mmol) in 1,2-dichloroethane (250 mL) was added dimethylcarbamic chloride (4.37 g, 40.66 mmol) and trimethylsilyl cyanide (4.03 g, 40.66 mmol) successively. The mixture was stirred under nitrogen at 80° C. overnight. The reaction mixture was quenched by adding sat'd. aq. NaHCO3 solution. The organic layer was washed with water (50 mL×3), dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with petroleum ether EtOAc (8:1) to afford 4.8 g (53%) of 6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile as a white solid. MS (ESI): m/z=332.0 [M+1]+.

Provenance & Evidence