4,4,5,5-Tetramethyl-2-(5-phenylpent-1-en-1-yl)-1,3,2-dioxaborolane → 7-[(1E)-5-phenylpent-1-enyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

HRID 37790

Reaction equation

HRID 37790 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([CH2:24][CH2:25][CH2:26][CH:27]=[CH:28]B2OC(C)(C)C(C)(C)O2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:18]1([CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]/[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 533991064,4,5,5-Tetramethyl-2-(5-phenylpent-1-en-1-yl)-1,3,2-dioxaborolaneHCID 672401637-bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Product 1

HCID 532509327-[(1E)-5-phenylpent-1-enyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Procedure

A suspension of the product of Example 1B (110 mg, 0.38 mmol) and 5-phenyl-1-pentenylboronic acid pinacol ester (123 mg, 0.45 mmol; Alfa) was processed as described in Example 4 to provide the title compound: 1H NMR (500 MHz, methanol-d4) δ ppm 1.79-1.90 (m, 2 H), 2.00-2.14 (m, 4 H), 2.28-2.37 (m, 2 H), 2.69 (t, J=7.0 Hz, 2 H), 3.00-3.08 (m, 2 H), 3.08-3.11 (m, 1 H), 3.22 (ddd, J=14.1, 8.5, 5.8 Hz, 2 H), 4.20 (s, 2 H), 6.33 (dt, J=15.9, 7.0 Hz, 1 H), 6.77 (d, J=15.9 Hz, 1 H), 6.93 (t, J=7.6 Hz, 1 H), 7.12-7.17 (m, 3 H), 7.18-7.22 (m, 2 H), 7.22-7.28 (m, 2 H); MS (APCI) m/z 357 (M+H)+. Anal. Calcd. for C25H28N2.0.2H2O: C, 83.38; H, 7.95; N, 7.78. Found: C, 83.29; H, 7.66; N, 7.68.

Sources & evidence

ORD record
ord-57180f2b40ca4d87923c17c2a2b4d129
Source dataset
uspto-grants-2013_09
Patent number
US08524703B2

Linked notes

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