B-[(1E)-2-(3-Fluorophenyl)ethenyl]boronic acid → 7-[(E)-2-(3-fluorophenyl)vinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

HRID 37797Notes

Reaction equation

HRID 37797 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.[F:18][C:19]1[CH:20]=[C:21](/[CH:25]=[CH:26]/B(O)O)[CH:22]=[CH:23][CH:24]=1>>[F:18][C:19]1[CH:20]=[C:21](/[CH:25]=[CH:26]/[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:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 16217749B-[(1E)-2-(3-Fluorophenyl)ethenyl]boronic acidHCID 672401637-bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Product 1

HCID 532511007-[(E)-2-(3-fluorophenyl)vinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Procedure

The product of Example 1B (120 mg, 0.41 mmol) and (E)-2-(3-fluorophenyl)vinylboronic acid (82 mg, 0.50 mmol; Aldrich) were processed as described in Example 4 to provide the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.93-2.01 (m, 4H), 2.88-3.02 (m, 2 H), 3.04-3.10 (m, 1 H), 3.11-3.22 (m, 2 H), 4.12 (s, 2 H), 6.98 (t, J=7.6 Hz, 1 H), 7.06-7.14 (m, 1 H), 7.22 (d, J=7.6 Hz, 1 H), 7.30 (d, J=16.2 Hz, 1 H), 7.38-7.42 (m, 1 H), 7.42-7.50 (m, 2 H), 7.52-7.58 (m, 1 H), 7.77 (d, J=16.5 Hz, 1 H); MS (DCI) m/z 333 (M+H)+.

Sources & evidence

ORD record
ord-7c7338e5db0a4f2db568b6f33cf85dc7
Source dataset
uspto-grants-2013_09
Patent number
US08524703B2

Reaction notes

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