N-Iodosuccinimide → tert-Butyl 2-(9-iodo-7-(4-Isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate
반응식
[CH:1]([O:4][C:5]1[CH:32]=[CH:31][C:8]([CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:17]3[N:16]4[CH2:20][CH2:21][CH:22]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:15]4=[CH:14][C:13]=3[CH:12]=2)=[CH:7][C:6]=1[C:33]([F:36])([F:35])[F:34])([CH3:3])[CH3:2].C1C(=O)N([I:44])C(=O)C1>C(Cl)Cl>[I:44][C:14]1[C:13]2[CH:12]=[C:11]([O:10][CH2:9][C:8]3[CH:31]=[CH:32][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[C:6]([C:33]([F:36])([F:34])[F:35])[CH:7]=3)[CH:19]=[CH:18][C:17]=2[N:16]2[CH2:20][CH2:21][CH:22]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:15]=12참가 물질
4
반응물 2
생성물 1
시약·촉매·용매 1
실험 절차
To a solution of tert-butyl 2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.722 g, 1.434 mmol) in DCM (24 mL) at 0° C. was added NIS (1.434 mmol). After 5 minutes, the reaction was diluted with DCM and washed with water (twice) and saturated sodium thiolsulfate (aq). The organics were dried over Na2SO4, filtered, and concentrated to give the title compound as a light-brown solid. LCMS m/z=630.5 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.29 (d, J=6.06 Hz, 6H), 1.38 (s, 9H), 2.27-2.38 (m, 1H), 2.51-2.56 (m, 1H), 2.77-2.89 (m, 1H), 2.94 (dd, J=15.92, 3.41 Hz, 1H), 3.51-3.61 (m, 1H), 3.99-4.09 (m, 1H), 4.12-4.21 (m, 1H), 4.74-4.83 (m, 1H), 5.10 (s, 2H), 6.78 (d, J=2.27 Hz, 1H), 6.85 (dd, J=8.72, 2.40 Hz, 1H), 7.25 (d, J=8.84 Hz, 1H), 7.30 (d, J=8.34 Hz, 1H), 7.66-7.73 (m, 2H).