反应详情

温度

60 °C

A mixture of 2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-3-carbonitrile (513.6 mg, 1.495 mmol), TBAI (55.2 mg, 0.150 mmol), cesium carbonate (1462 mg, 4.49 mmol), and ethyl bromoacetate (250 μl, 2.243 mmol) in DMF (7.5 ml) was heated at 60° C. for 4 hours. The mixture was diluted in ethyl acetate (100 ml) and washed with water (50 ml×3). The organic layer was dried, filtered, and evaporated to give an oil. This oil was purified by column chromatography (0 to 40% ethyl acetate in hexanes) to give ethyl 2-(3-cyano-2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (286.9 mg, 0.668 mmol, 44.7% yield). 1H NMR (CDCl3/400 MHz) δ (ppm) 7.92-7.88 (m, 1H), 7.44-7.38 (m, 1H), 7.35-7.29 (m, 1H), 6.96-6.92 (m, 1H), 4.36 (s, 2H), 4.28 (s, 2H), 3.94 (q, 2H), 3.38-3.30 (m, 4H), 2.27 (s, 3H), 2.13 (s, 3H), 1.98-1.92 (m, 4H), 1.11 (t, 3H). MS m/z: 430.3 (M+1).

1. washwashed with water (50 ml×3)
2. customThe organic layer was dried
3. filtrationfiltered
4. customevaporated
5. customto give an oil
6. customThis oil was purified by column chromatography (0 to 40% ethyl acetate in hexanes)