Dimethylformamide → 6-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

In a 25 mL round-bottomed flask, 6-(4-methylpiperazin-1-yl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (320 mg, 859 μmol, Eq: 1.00) was combined with DMF (11.8 ml) to give a colorless solution. The reaction mixture was cooled to −20° C. and stirred for 5 min. Chlorosulfonyl isocyanate (365 mg, 224 μl, 2.58 mmol, Eq: 3) in acetonitrile (11.8 ml) was added dropwise and the resultant cooled reaction was stirred at −20° C. and stirred for 3 hrs The reaction mixture was poured into 25 mL EtOAc and extracted with sat NaCl (3×20 mL). The crude material was purified by flash chromatography (silica gel, 12 g, 5% to 10% MeOH in DCM) to give 6-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (113 mg, 55%).

Provenance & Evidence