Toluene → Methyl 1-methyl-5-sulfamoyl-1h-pyrrole-2-carboxylate

Participants

Reaction Steps

5-(Aminosulfonyl)-1-methyl-1H-pyrrole-2-carboxylic acid (1310 mg; 6.42 mmol; 1 eq.), commercially available (ASDI), is dissolved in MeOH (24 ml), then toluene (8 ml) is added followed by the dropwise addition of (trimethylsilyl)diazomethane (9.62 ml; 2M; 19.25 mmol; 3 eq). The solution is stirred at r.t. for 2 hr and another equivalent of (trimethylsilyl)diazomethane (3.21 ml; 2 M; 6.42 mmol; 1 eq) is added to reaction mixture. After 1 hr stirring, the solvent is concentrated to dryness and the resulting off white solid is recrystallized in MeOH to afford 851.1 mg (61%) of the title compound. 1H NMR (DMSO-d6) δ 7.58 (d, J=1.5 Hz, 1H), 7.13 (s, 2H), 7.06 (d, J=1.9 Hz, 1H), 3.88 (s, 3H), 3.77 (s, 3H). HPLC (max plot) 100%; Rt 1.19 min. LC/MS: (ES−) 217.1.

Provenance & Evidence