Sulfuric acid magnesium salt (1:1) → 7-[(E)-2-(pyrimidin-5-yl)vinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole
Reaction equation
Br[C:2]1[C:10]2[NH:9][C:8]3[CH:11]4[CH2:17][CH2:16][N:14]([CH2:15][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH2:13][CH2:12]4.[CH:18]([C:20]1[CH:21]=[N:22][CH:23]=[N:24][CH:25]=1)=[CH2:19].S([O-])([O-])(=O)=O.[Mg+2]>>[N:22]1[CH:21]=[C:20](/[CH:18]=[CH:19]/[C:2]2[C:10]3[NH:9][C:8]4[CH:11]5[CH2:17][CH2:16][N:14]([CH2:15][C:7]=4[C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12]5)[CH:25]=[N:24][CH:23]=1Participants
4
Procedure
The product of Example 1B (265 mg, 0.91 mmol), the product of Example 29A (193 mg, 1.82 mmol) and magnesium sulfate (55 mg, 0.46 mmol) were combined and processed as described in Example 1D to provide the title compound as the slower eluting compound: 1H NMR (400 MHz, methanol-d4) δ ppm 2.04-2.20 (m, 4 H), 3.04-3.17 (m, 3 H), 3.22-3.30 (m, 2 H), 4.26 (s, 2 H), 7.05 (t, J=7.6 Hz, 1 H), 7.24 (d, J=16.8 Hz, 1 H), 7.31 (dd, J=7.9, 0.9 Hz, 1 H), 7.43-7.47 (m, J=7.3 Hz, 1 H), 7.89 (s, 1 H), 9.02 (d, J=16.1 Hz, 1 H), 9.04 (s, 2 H); MS (APCI) m/z 317 (M+H)+.
Sources & evidence
- ORD record
- ord-ed1bbed5db284f9d970626265a2f85cf
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524703B2
Reaction notes
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