5-Ethynyl-2-methylpyridine → HCID 45381859, compound

HRID 2176163Notes

Reaction equation

HRID 2176163 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]=[CH:26][C:27]([CH3:30])=[N:28][CH:29]=1)#[CH:23]>>[CH3:30][C:27]1[N: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][CH:26]=1

Participants

3

Reactant 2

HCID 6381975-Ethynyl-2-methylpyridineHCID 67545385HCID 67545385, compound

Product 1

HCID 45381859HCID 45381859, 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 5-ethynyl-2-methylpyridine (111 mg, 0.945 mmol; prepared as described in International Publication No. WO2005090333) was performed according to the procedure described in Example 20 to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 1.66-1.80 (m, 2H), 1.84-1.98 (m, 2H), 2.40 (s, 3H), 2.95-3.23 (m, 5H), 4.24 (s, 2H), 6.83 (d, J=8 Hz, 1H), 6.92-6.99 (m, 2H), 7.06-7.16 (m, 3H), 7.28 (s, 1H), 7.85 (s, 1H); MS (DCI/NH3) m/z 414 (M+H)+.

Sources & evidence

ORD record
ord-2f91df7f28994dfabb4027f992ec7a44
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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