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

HRID 37812Notes

Reaction equation

HRID 37812 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][CH:21]=[C:20](B(O)O)[CH:19]=1>>[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([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:19]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 672401637-bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Product 1

HCID 532515817-(pyridin-3-yl)-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Procedure

The product of Example 1B (80 mg, 0.28 mmol) and pyridine-3-boronic acid (36 mg, 0.29 mmol; Aldrich) were processed as described in Example 4 to provide the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 2.00-2.14 (m, 4 H), 3.01-3.15 (m, 3 H), 3.20-3.28 (m, 2 H), 4.27 (s, 2 H), 7.04-7.09 (m, 1 H), 7.12 (t, J=7.3 Hz, 1 H), 7.37 (dd, J=7.5, 1.4 Hz, 1 H), 7.56 (dd, J=7.8, 5.1 Hz, 1 H), 8.05-8.12 (m, 1 H), 8.55 (dd, J=4.9, 1.5 Hz, 1H), 8.77-8.79 (m, 1 H); MS (ESI+) m/z 290 (M+H)+.

Sources & evidence

ORD record
ord-ff3250d744a5464d96a838caa109497c
Source dataset
uspto-grants-2013_09
Patent number
US08524703B2

Reaction notes

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