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

HRID 37792

Reaction equation

HRID 37792 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]=1

Participants

3

Reactant 2

HCID 88172-Methyl-5-vinylpyridineHCID 672389759-bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Product 1

HCID 532509359-[(E)-2-(6-methylpyridin-3-yl)vinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

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)+.

Sources & evidence

ORD record
ord-4326653e7c764e07903b871709a6edc9
Source dataset
uspto-grants-2013_09
Patent number
US08524703B2

Linked notes

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