(Pyridin-4-yl)boronic acid → 7-(pyridin-4-yl)-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

HRID 37813Notes

Reaction equation

HRID 37813 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.[N:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>>[N:18]1[CH:23]=[CH:22][C:21]([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:20][CH:19]=1

Participants

3

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 672401637-bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Product 1

HCID 532515827-(pyridin-4-yl)-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 pyridine-4-boronic acid (52 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 2.06-2.17 (m, 4 H), 3.06-3.18 (m, 3 H), 3.23-3.29 (m, 2 H), 4.30 (s, 2 H), 7.13 (t, J=7.6 Hz, 1 H), 7.17-7.20 (m, 1 H), 7.41 (dd, J=7.6, 1.2 Hz, 1 H), 7.70-7.74 (m, 2 H), 8.58-8.64 (m, 2 H); MS (APCI) m/z 290 (M+H)+.

Sources & evidence

ORD record
ord-65c844f4230841758a895a43916beda3
Source dataset
uspto-grants-2013_09
Patent number
US08524703B2

Reaction notes

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