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

HRID 37794

Reaction equation

HRID 37794 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][CH:23]=[CH:22][N:21]=1)=[CH2:19]>>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1/[CH:18]=[CH:19]/[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

Participants

3

Reactant 2

HCID 75212-VinylpyridineHCID 672401637-bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Product 1

HCID 532510997-[(E)-2-pyridin-2-ylvinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Procedure

The product of Example 1B (110 mg, 0.38 mmol; Aldrich) and 2-vinylpyridine (40 mg, 0.38 mmol; Aldrich) were processed as described in Example 1D to provide the title compound: 1H NMR (500 MHz, methanol-d4) δ ppm 2.04-2.17 (m, 4 H), 3.04-3.12 (m, 2 H), 3.13-3.17 (m, 1 H), 3.26 (ddd, J=14.1, 8.5, 5.8 Hz, 2 H), 4.25 (s, 2 H), 7.04 (t, J=7.6 Hz, 1 H), 7.26 (ddd, J=7.4, 5.0, 1.1 Hz, 1 H), 7.28-7.34 (m, 2 H), 7.41 (d, J=7.3 Hz, 1 H), 7.71-7.74 (m, J=7.9 Hz, 1 H), 7.82 (td, J=7.6, 1.8 Hz, 1 H), 7.93-8.01 (m, 1 H), 8.51 (dd, J=5.0, 0.8 Hz, 1 H); MS (APCI) m/z 316 (M+H)+.

Sources & evidence

ORD record
ord-925afa78c9aa452fa5c2197ce82c964a
Source dataset
uspto-grants-2013_09
Patent number
US08524703B2

Linked notes

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