Styrylboronic acid → 7-[(E)-2-phenylvinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

HRID 37798Notes

Reaction equation

HRID 37798 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.[C:18]1(/[CH:24]=[CH:25]/B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:18]1(/[CH:24]=[CH:25]/[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:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 5702628Styrylboronic acidHCID 672401637-bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Product 1

HCID 532517367-[(E)-2-phenylvinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Procedure

The product of Example 1B (100 mg, 0.34 mmol) and (E)-phenylethenylboronic acid (56 mg, 0.38 mmol; Aldrich) were processed as described in Example 4 to provide the title compound: 1H NMR (400 MHz, methanol-d4) δ ppm 2.03-2.18 (m, 4 H), 3.04-3.13 (m, 2 H), 3.13-3.18 (m, 1 H), 3.21-3.28 (m, 2 H), 4.24 (s, 2 H), 7.01 (t, J=7.6 Hz, 1 H), 7.19-7.28 (m, 3 H), 7.32-7.41 (m, 3 H), 7.60 (d, J=12.2 Hz, 1 H), 7.62-7.65 (m, 2 H); MS (DCI) m/z 315 (M+H)+.

Sources & evidence

ORD record
ord-d2225f2958c449bab0a63afe23e45002
Source dataset
uspto-grants-2013_09
Patent number
US08524703B2

Reaction notes

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