3-Methyl-6-vinylpyridazine → 9-methyl-6-[2-(6-methylpyridazin-3-yl)ethyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

HRID 2176142Notes

Reaction equation

HRID 2176142 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH:11]4[CH2:17][CH2:16][N:14]([CH2:15][C:5]=3[C:4]=2[CH:3]=1)[CH2:13][CH2:12]4.[CH3:18][C:19]1[N:20]=[N:21][C:22]([CH:25]=[CH2:26])=[CH:23][CH:24]=1>>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:26][CH2:25][C:22]3[N:21]=[N:20][C:19]([CH3:18])=[CH:24][CH:23]=3)[C:6]3[CH:11]4[CH2:12][CH2:13][N:14]([CH2:15][C:5]=3[C:4]=2[CH:3]=1)[CH2:16][CH2:17]4

Participants

3

Reactant 2

HCID 668487113-Methyl-6-vinylpyridazineHCID 67544841HCID 67544841, compound

Product 1

HCID 453806619-methyl-6-[2-(6-methylpyridazin-3-yl)ethyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Procedure

Under nitrogen, 9-methyl-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole (260 mg, 1.15 mmol, Example 2B), was coupled with 3-methyl-6-vinylpyridazine (280 mg, 1.86 mmol, Example 148B) according to the procedure described in Example 1B to give the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 1.65-1.76 (m, 2H) 1.85-1.95 (m, 2H) 2.43 (s, 3H) 2.67 (s, 3H) 2.96-3.09 (m, 3H) 3.17-3.25 (m, 2H) 3.30 (t, J=7.1 Hz, 2H) 4.23 (s, 2H) 4.55 (t, J=7.1 Hz, 2H) 6.82 (d, J=8.5 Hz, 1H) 6.96 (dd, J=8.3, 1.2 Hz, 1H) 7.11 (dd, J=17.1, 8.4 Hz, 2H) 7.16 (s, 1H); MS (DCI/NH3) m/z 347 (M+H)+.

Sources & evidence

ORD record
ord-bcb4b7fd3a384a95a4137e4445f73827
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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