5-Ethynyl-2-methylpyridine → HCID 45381772, compound

HRID 2176167Notes

Reaction equation

HRID 2176167 reaction equation
[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:11]2[NH:10][C:9]3[CH:14]4[CH2:20][CH2:19][N:17]([CH2:18][C:8]=3[C:7]=2[CH:6]=1)[CH2:16][CH2:15]4)(=[O:4])=[O:3].[C:21]([C:23]1[CH:24]=[CH:25][C:26]([CH3:29])=[N:27][CH:28]=1)#[CH:22]>>[CH3:29][C:26]1[N:27]=[CH:28][C:23](/[CH:21]=[CH:22]\[N:10]2[C:11]3[CH:12]=[CH:13][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][C:7]=3[C:8]3[CH2:18][N:17]4[CH2:16][CH2:15][CH:14]([C:9]2=3)[CH2:20][CH2:19]4)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 6381975-Ethynyl-2-methylpyridineHCID 67545581HCID 67545581, compound

Product 1

HCID 45381772HCID 45381772, compound

Procedure

The coupling of 9-(methylsulfonyl)-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole (150 mg, 0.517 mmol; Example 180) and 5-ethynyl-2-methylpyridine (182 mg, 1.55 mmol; prepared as described in International Publication No. WO2005090333) was performed according to the procedure described in Example 20 to afford the title compound as the major product: 1H NMR (300 MHz, methanol-d4) δ ppm 1.70-1.82 (m, 2H), 1.88-2.01 (m, 2H), 2.40 (s, 3H), 2.96-3.24 (m, 5H), 3.10 (s, 3H), 4.32 (s, 2H), 6.91 (d, J=8 Hz, 1H), 7.00 (d, J=8 Hz, 1H), 7.09 (s, 2H), 7.32 (d, J=9 Hz, 1H), 7.61 (dd, J=9, 2 Hz, 1H), 7.87 (s, 1H), 8.04 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 408 (M+H)+.

Sources & evidence

ORD record
ord-763b0b3f15fb447483ab80dca612eae0
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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