ethyl 2-oxo-2-(1H-pyrrol-2-yl)acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Alternatively, a mixture of 5-aminosulfonylindolin-2-one (1.0 g, 4.7 mmol), 2-ethoxycarbonylcarbonylpyrrole (2.5 g, 14.5 mmol) in ethanol (120 mL) was treated with triethylamine (1.0 mL, 7.2 mmol). The reaction mixture was refluxed for 24 hours. The reaction mixture was concentrated to approximately 20 mL, treated with additional triethylamine (0.2 mL, 1.44 mmol) and refluxed for 55 hoursr. The reaction was then cooled to ambient temperature and concentrated. Reverse phase HPLC using acetonitrile/water afforded 5-aminosulfonyl-3-[(pyrrol-2-yl)(ethoxycarbonyl)methylene]indolin-2-one; 1H NMR (400 MHz, DMSO-d6) δ 1.35 (t, 3H), 4.50 (q, 2H), 6.40 (s, 1H), 6.65 (s, 1H), 7.06 (d, 1H), 7.25(s, 2H), 7.48 (br s, 1H), 7.50 (s, 1H), 7.68 (d, 1H), 11.50 (s, 1H) ppm; (45 mg) and 5-aminosulfonyl-3-[(pyrrol-2-yl)(carboxy)methylene]indolin-2-one; 1H NMR (400 MHz, DMSO-d6) δ 6.40 (s, 1H), 6.65 (s, 1H), 7.06 (d, 1H), 7.25 (s, 2H), 7.48 (br s, 1H), 7.68 (d, 1H), 7.85 (s, 1H), 11.50 (s, 1H) ppm; (48 mg). The reaction mixture was refluxed for 24 hours The reaction mixture was concentrated to approximately 20 mL refluxed for 55 hoursr concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Alternatively, a mixture of 5-aminosulfonylindolin-2-one (1.0 g, 4.7 mmol), 2-ethoxycarbonylcarbonylpyrrole (2.5 g, 14.5 mmol) in ethanol (120 mL) was treated with triethylamine (1.0 mL, 7.2 mmol). The reaction mixture was refluxed for 24 hours. The reaction mixture was concentrated to approximately 20 mL, treated with additional triethylamine (0.2 mL, 1.44 mmol) and refluxed for 55 hoursr. The reaction was then cooled to ambient temperature and concentrated. Reverse phase HPLC using acetonitrile/water afforded 5-aminosulfonyl-3-[(pyrrol-2-yl)(ethoxycarbonyl)methylene]indolin-2-one; 1H NMR (400 MHz, DMSO-d6) δ 1.35 (t, 3H), 4.50 (q, 2H), 6.40 (s, 1H), 6.65 (s, 1H), 7.06 (d, 1H), 7.25(s, 2H), 7.48 (br s, 1H), 7.50 (s, 1H), 7.68 (d, 1H), 11.50 (s, 1H) ppm; (45 mg) and 5-aminosulfonyl-3-[(pyrrol-2-yl)(carboxy)methylene]indolin-2-one; 1H NMR (400 MHz, DMSO-d6) δ 6.40 (s, 1H), 6.65 (s, 1H), 7.06 (d, 1H), 7.25 (s, 2H), 7.48 (br s, 1H), 7.68 (d, 1H), 7.85 (s, 1H), 11.50 (s, 1H) ppm; (48 mg). The reaction mixture was refluxed for 24 hours The reaction mixture was concentrated to approximately 20 mL refluxed for 55 hoursr concentrated