2-Methyl-5-vinylpyridine → 9-[(E)-2-(6-methylpyridin-3-yl)vinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[CH:4][N:3]=1.Br[C:11]1[CH:19]=[CH:18][C:17]2[NH:16][C:15]3[CH:20]4[CH2:26][CH2:25][N:23]([CH2:24][C:14]=3[C:13]=2[CH:12]=1)[CH2:22][CH2:21]4>>[CH3:1][C:2]1[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:11]2[CH:19]=[CH:18][C:17]3[NH:16][C:15]4[CH:20]5[CH2:26][CH2:25][N:23]([CH2:24][C:14]=4[C:13]=3[CH:12]=2)[CH2:22][CH2:21]5)=[CH:6][CH:7]=1Participants
3
Procedure
The product of Example 1C (133 mg, 1.11 mmol) and the product of Example 8A (180 mg, 0.62 mmol) were processed as described in Example 1D to provide the title compound: 1H NMR (500 MHz, methanol-d4) δ ppm 2.03-2.14 (m, 4 H), 2.52 (s, 3 H), 2.98-3.04 (m, 1 H), 3.08 (dt, J=14.0, 6.9 Hz, 2 H), 3.20-3.29 (m, 2 H), 4.27 (s, 2 H), 7.05 (d, J=16.2 Hz, 1 H), 7.27 (d, J=8.2 Hz, 2 H), 7.33 (d, J=16.2 Hz, 1 H), 7.35-7.38 (m, 1 H), 7.49 (s, 1 H), 7.94 (dd, J=7.9, 2.1 Hz, 1 H), 8.50 (d, J=1.8 Hz, 1 H); MS (APCI) m/z 330 (M+H)+.