3-Ethynylpyridine → HCID 45381860, compound

HRID 2176162Notes

Reaction equation

HRID 2176162 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]3[CH:13]4[CH2:19][CH2:18][N:16]([CH2:17][C:7]=3[C:6]=2[CH:5]=1)[CH2:15][CH2:14]4.[C:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)#[CH:23]>>[N:26]1[CH:27]=[CH:28][CH:29]=[C:24](/[CH:22]=[CH:23]/[N:9]2[C:10]3[CH:11]=[CH:12][C:4]([O:3][C:2]([F:1])([F:20])[F:21])=[CH:5][C:6]=3[C:7]3[CH2:17][N:16]4[CH2:15][CH2:14][CH:13]([C:8]2=3)[CH2:19][CH2:18]4)[CH:25]=1

Participants

3

Reactant 2

HCID 1860033-EthynylpyridineHCID 67545385HCID 67545385, compound

Product 1

HCID 45381860HCID 45381860, compound

Procedure

The coupling of 9-(trifluoromethoxy)-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole (140 mg, 0.473 mmol; Example 175) and 3-ethynylpyridine (97 mg, 0.945 mmol; Aldrich) was performed according to the procedure described in Example 20 to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 2.09-2.18 (m, 4H), 3.03-3.16 (m, 2H), 3.19-3.29 (m, 2H), 3.42-3.49 (m, 1H), 4.25 (s, 2H), 6.86 (d, J=14 Hz, 1H), 7.10 (ddd, J=9, 2, 1 Hz, 1H), 7.28 (d, J=1 Hz, 1H), 7.45 (dd, J=8, 5 Hz, 1H), 7.72 (d, J=9 Hz, 1H), 7.79 (d, J=15 Hz, 1H), 8.10 (dt, J=8, 2 Hz, 1H), 8.43 (dd, J=5, 2 Hz, 1H), 8.71 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 400 (M+H)+.

Sources & evidence

ORD record
ord-103fd6fe37ba42939afe5bb19101b892
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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