2-Methyl-5-vinylpyridine → 5-[2-(6-Methylpyridin-3-yl)ethyl]-2-(trifluoromethoxy)-6,7,8,9,10,11-hexahydro-5h-7,11-epiminocycloocta[b]indole

HRID 2176133Notes

Reaction equation

HRID 2176133 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]1[CH2:13][CH:14]3[NH:19][CH:18]([C:7]2=1)[CH2:17][CH2:16][CH2:15]3.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]=[CH2:30])=[CH:25][N:24]=1>>[CH3:22][C:23]1[N:24]=[CH:25][C:26]([CH2:29][CH2:30][N:9]2[C:10]3[C:6](=[CH:5][C:4]([O:3][C:2]([F:1])([F:20])[F:21])=[CH:12][CH:11]=3)[C:7]3[CH:18]4[NH:19][CH:14]([CH2:13][C:8]2=3)[CH2:15][CH2:16][CH2:17]4)=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 88172-Methyl-5-vinylpyridineHCID 67545688HCID 67545688, compound

Product 1

HCID 675452345-[2-(6-Methylpyridin-3-yl)ethyl]-2-(trifluoromethoxy)-6,7,8,9,10,11-hexahydro-5h-7,11-epiminocycloocta[b]indole

Procedure

The coupling of 2-trifluoromethoxy-6,7,8,9,10,11-hexahydro-5H-7,11-epiminocycloocta[b]indole (148 mg, 0.500 mmol; Example 140A) and 2-methyl-5-vinylpyridine (119 mg, 1.00 mmol; IBScreen) was performed according to the procedure described in Example 114B to afford the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 1.09-1.22 (m, 1H), 1.29-1.39 (m, J=7, 7 Hz, 1H), 1.46 (d, J=14 Hz, 1H), 1.75 (d, J=14 Hz, 1H), 2.26-2.44 (m, 3H), 2.48 (s, 3H), 2.95-3.04 (m, 1H), 3.05-3.13 (m, 1H), 3.47 (dd, J=18, 7 Hz, 1H), 4.22-4.31 (m, 1H), 4.34-4.43 (m, 2H), 5.29 (s, 1H), 6.99 (d, J=8 Hz, 1H), 7.23-7.31 (m, 2H), 7.51 (d, J=9 Hz, 1H), 7.60 (s, 1H), 8.37 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 416 (M+H)+.

Sources & evidence

ORD record
ord-c3e1f1e41fc44ff790563aa00a55b969
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

Loading…