Dimethylformamide → 6-(1,1-dioxo-1lambda*6*-thiomorpholin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

In a 25 mL round-bottomed flask 6-(1,1-Dioxo-1lambda*6*-thiomorpholin-4-yl)-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (322 mg, 790 μmol, Eq: 1.00) was combined with DMF (11.9 ml) to give a colorless solution. The reaction mixture was cooled to −20° C. and stirred for 5 min. Chlorosulfonyl isocyanate (335 mg, 206 μl, 2.37 mmol, Eq: 3) in acetonitrile (11.9 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 washed with sat NaCl (3×20 mL). After evaporation, crude material was purified by flash chromatography (silica gel, 12 g, 5% to 10% MeOH in DCM) to obtain 6-(1,1-dioxo-1lambda*6*-thiomorpholin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (122 mg, 56%).

Provenance & Evidence