4-Vinylpyridine → 7-[(E)-2-pyridin-4-ylvinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

HRID 37793

Reaction equation

HRID 37793 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:25]=[CH:24][N:23]=[CH:22][CH:21]=1)=[CH2:19].[O-]S([O-])(=O)=O.[Mg+2]>>[N:23]1[CH:24]=[CH:25][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:21][CH:22]=1

Participants

4

Reactant 3

HCID 75024-VinylpyridineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 672401637-bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Product 1

HCID 532510987-[(E)-2-pyridin-4-ylvinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Procedure

The product of Example 1B (100 mg, 0.34 mmol), 4-vinylpyridine (144 mg, 1.37 mmol; Aldrich) and MgSO4 (83 mg, 0.69 mmol) were combined and processed as described in Example 1D to provide the title compound: 1H NMR (400 MHz, methanol-d4) δ ppm 1.97-2.22 (m, 4 H), 3.03-3.12 (m, 2 H), 3.13-3.18 (m, 1 H), 3.21-3.29 (m, 2 H), 4.24 (s, 2 H), 7.04 (t, J=7.6 Hz, 1 H), 7.24 (d, J=16.5 Hz, 1 H), 7.31 (dd, J=7.8, 0.8 Hz, 1 H), 7.44 (d, J=7.6 Hz, 1 H), 7.59-7.69 (m, 2 H), 7.94 (d, J=16.5 Hz, 1 H), 8.46-8.50 (m, 2 H); MS (APCI) m/z 316 (M+H)+.

Sources & evidence

ORD record
ord-7ded72baff6e4dc2a6c0f5caf89b3cd0
Source dataset
uspto-grants-2013_09
Patent number
US08524703B2

Linked notes

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