反应详情

1-[6-(1-benzyl-pyrrolidin-3-ylamino)-2,3-dihydro-indol-1-yl]-ethanone. The desired intermediate (84 mg, 44%) was prepared as in Example 39, Step A, using 1-benzyl-3-pyrrolidinone (0.20 g, 1.1 mmol), 1-acetyl-6-aminoindoline (0.10 g, 0.57 mmol), Na(OAc)3BH (360 mg, 1.7 mmol), and AcOH (171 μL, 3.0 mmol) in 1,2-dichloroethane (10 mL). 1H NMR (500 MHz, CDCl3): 7.61 (s, 1H), 7.35-7.28 (m, 4H), 7.28-7.20 (m, 1H), 6.93 (d, J=8.1 Hz,1H), 6.24 (dd, J=8.2, 1.9 Hz, 1H), 4.05-3.96 (m, 3H), 3.68-3.56 (m, 2H), 3.10-3.01 (m, 2H), 2.80-2.71 (m, 2H), 2.59-2.51 (m, 1H), 2.48-2.39 (m, 1H), 2.38-2.22 (m, 1H), 2.20 (s, 3H), 1.71-1.56 (m, 1H). MS: exact mass calculated for C21H25N3O, 335.20; m/z found, 336.1 [M+H]+. Step B. The above intermediate (49 mg, 0.29 mmol) was reacted with with cinnamoyl chloride (2 76 mg, 0.2 mmol) as in Example 2, Step C to provide 79 mg (74%) of the desired product. 1H NMR (500 MHz, CDCl3): 8.09 (s, 1H), 7.62 (d, J=15.5 Hz, 1H), 7.30-7.15 (m, 1H), 6.78 (d, J=7.0 Hz, 1H), 6.17 (d, J=15.5 Hz, 1H), 5.15-5.05 (br m, 1H), 4.19-4.08 (m, 2H), 3.70-3.51 (m, 2H), 3.29-3.20 (m, 2H), 3.07-2.95 (br m, 1H), 2.76-2.57 (br m, 3H), 2.30-2.22 (m, 1H), 2.21 (s, 3H), 1.98-1.83 (m, 1H). MS: exact mass calculated for C30H31N3O2, 465.24; m/z found, 466.2 [M+H]+.