2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 7-(6-Methylpyridin-3-yl)-1,2,3,4,5,6-hexahydro-1,4-methanoazepino[4,3-b]indole

HRID 1623058Notes

Reaction equation

HRID 1623058 reaction equation
Br[C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH:12]4[CH2:16][CH:15]([C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1)[NH:14][CH2:13]4.[CH3:17][C:18]1[N:23]=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][CH:19]=1>>[CH3:17][C:18]1[N:23]=[CH:22][C:21]([C:2]2[C:10]3[NH:9][C:8]4[CH2:11][CH:12]5[CH2:16][CH:15]([C:7]=4[C:6]=3[CH:5]=[CH:4][CH:3]=2)[NH:14][CH2:13]5)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 164142722-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 672388157-Bromo-1,2,3,4,5,6-hexahydro-1,4-methanoazepino[4,3-b]indole

Product 1

HCID 532526477-(6-Methylpyridin-3-yl)-1,2,3,4,5,6-hexahydro-1,4-methanoazepino[4,3-b]indole

Procedure

The product of Example 30A (55 mg, 0.20 mmol) and 6-methylpyridine-3-boronic acid pinacol ester (44 mg, 0.20 mmol; Synthonix) were processed as described in Example 11 to provide the title compound: 1H NMR (400 MHz, methanol-d4) δ ppm 1.99-2.05 (m, 1H), 2.09-2.17 (m, 1H), 2.60 (s, 3H), 2.88 (dd, J=17.1, 2.4 Hz, 1H), 3.12-3.20 (m, 2H), 3.23-3.28 (m, 1H), 3.57 (t, J=3.4 Hz, 1H), 4.05 (dt, J=5.5, 2.7 Hz, 1H), 7.01-7.05 (m, 1H), 7.11 (t, J=7.5 Hz, 1H), 7.42 (d, J=8.2 Hz, 1H), 7.50 (dd, J=7.8, 1.1 Hz, 1H), 7.94 (dd, J=7.9, 2.1 Hz, 1H), 8.61 (d, J=2.1 Hz, 1H); MS (ESI+) m/z 290 (M+H)+.

Sources & evidence

ORD record
ord-b1fc3fc8873843c9b3fb4c69490934c0
Source dataset
uspto-grants-2014_07
Patent number
US08778959B2

Reaction notes

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