[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][CH:5]=[C:4]([CH:11]([CH3:15])C(O)=O)[C:3]1=2.[C:16]([N:23]1[CH:27]=[CH:26]N=[CH:24]1)(N1C=CN=C1)=[O:17].N1CCC[CH2:29]1.O>ClCCl>[O:17]=[C:16]([N:23]1[CH2:24][CH2:29][CH2:26][CH2:27]1)[CH2:15][CH2:11][C:4]1[C:3]2[C:2](=[O:1])[CH2:10][CH2:9][CH2:8][C:7]=2[NH:6][CH:5]=1To a suspension of 10 g of 3-(4-oxo-4,5,6,7,tetrahydro-1H-indol-3-yl-propionic acid (48 mmol) in 60 mL of dichloromethane was added 9.3 g (57.6 mmol) of carbonyldiimidazole. After stirring at room temperature for 2 hours, 12 mL (144 mmol) of pyrrolidine was added. The dark red reaction mixture was then stirred at room temperature overnight. The reaction was poured into water and the organic layer washed with brine, dried and concentrated to give 3-(3-oxo-3-pyrrolidin-1-yl-propyl)-1,5,6,7-tetrahydro-indol-4-one (12 g, 96% yield). 1H-NMR (300 MHz, dimethylsulfoxide-d6) δ 11.05 (br s, 1H, NH), 6.46 (d, 1H), 3.35 (m, 2H, CH2), 2.24 (m, 2H, CH2), 2.66–2.73 (m, 4H, 2×CH2), 2.44 (m, 2H, CH2), 2.26 (m, 2H, CH2), 1.96 (m, 2H, CH2), 1.82 (m, 2H, CH2), 1.73 (m, 2H, CH2). MS m/z 260 [M+].
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