Isopropyl chloroformate → {2-dimethylcarbamoyl-6-fluoro-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-carbamic Acid Isopropyl Ester

Participants

Reaction Conditions

Reaction Steps

45 mg (0.08 mmol) of 2-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide was dissolved in 1.0 mL dichloromethane and 1.0 mL of a saturated aqueous solution of sodium bicarbonate was added. The biphasic solution was cooled to 0° C. in an ice bath and, while stirring vigorously, 161 μL (0.161 mmol) of 1 M isopropyl chloroformate in toluene was added. The reaction was allowed to stir in the ice bath and allowed to warm to room temperature overnight (16 hours). The layers were separated and the organic layer was washed twice with water. The organic layer was then dried over sodium sulfate and concentrated. MS: m/z 645.1 (M+H+).

Provenance & Evidence