Sodium Hydroxide → methyl 1-(3-(dimethylcarbamoyl)-4-methoxyphenylsulfonyl)-1H-pyrrole-2-carboxylate

Participants

Reaction Steps

To a mixture of methyl 1H-pyrrole-2-carboxylate (135 mg, 1.080 mmol), tetrabutylammonium hydrogensulfate (36.7 mg, 0.108 mmol) and sodium hydroxide (389 mg, 9.72 mmol) in water (2 ml) and DCM (4 ml) under vigorous stirring, a solution of 3-(dimethylcarbamoyl)-4-methoxybenzene-1-sulfonyl chloride (Int. 9) (300 mg, 1.080 mmol) in DCM (5 ml) was added drop-wise at RT over 10 minutes, and the reaction was stirred at the same temperature for 24 hours. The mixture was diluted with water and DCM, the organic phase was separated, washed with brine and dried over sodium sulfate. The solvent was evaporated under vacuum yielding methyl 1-(3-(dimethylcarbamoyl)-4-methoxyphenylsulfonyl)-1H-pyrrole-2-carboxylate (Int. 10) (260 mg, 0.710 mmol, MS/ESI+367.0 [MH]+) which was used as such in the next step.

Provenance & Evidence