反应详情

温度

80 °C

The crude (2-chloro-4-cyanophenyl)-[5-(2-methanesulfonyloxyethyl)imidazol-1-yl]-acetic acid methyl ester (2.56 g, 6.45 mmol) is dissolved in dry DMF (50 mL) and to it is added K2CO3 (2.67 g, 19.4 mmol), NaI (2.9 g, 19.4 mmol) and Et3N (2.7 mL, 19.4 mmol). The reaction is stirred at 80° C. for 2 h before being concentrated to dryness. The residue is then diluted with EtOAc and washed with water. The organic layer is dried (Na2SO4) and evaporated to give a crude residue that is purified via flash column chromatography (Acetone/CH2Cl2 1:3) to give 5-(2-chloro-4-cyanophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-5-carboxylic acid methyl ester as an oil. MS (ESI) m/z 302.2, 304.2 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 2.64-2.76 (m, 2H), 2.97-3.06 (m, 1H), 3.84 (s, 3H), 3.86-3.93 (m, 1H), 6.56 (d, J=8.1 Hz, 1H), 6.87 (s, 1H), 7.50 (obs d, J=8.1 Hz, 1H), 7.52 (s, 1H), 7.73 (s, 1H).

1. concentrationbefore being concentrated to dryness
2. additionThe residue is then diluted with EtOAc
3. washwashed with water
4. dry with materialThe organic layer is dried (Na2SO4)
5. customevaporated
6. customto give a crude residue that
7. customis purified via flash column chromatography (Acetone/CH2Cl2 1:3)