5-Ethynyl-2-methylpyridine → HCID 67543477, compound
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH2:11][CH:12]3[NH:16][CH:15]([C:5]2=1)[CH2:14][CH2:13]3.[C:17]([C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[N:23][CH:24]=1)#[CH:18]>>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](/[CH:18]=[CH:17]\[C:19]1[CH:24]=[N:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[C:6]1[CH2:11][C@@H:12]3[NH:16][C@H:15]([C:5]2=1)[CH2:14][CH2:13]3Participants
Procedure
The coupling of 2-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole (212 mg, 1.00 mmol; Example 4A) and 5-ethynyl-2-methylpyridine (586 mg, 5.00 mmol; International Publication No. WO2005090333) was performed as described in Example 20 to afford the racemate of the title compound. The individual enantiomers were separated by preparative chiral supercritical fluid chromatography (ChiralPak® OD-H 5 μm column, 21×250 mm, 35° C., 10-50% gradient of CH3OH—CO2 containing 0.1% diethylamine) to afford the title compound as the first-eluting peak: 1H NMR (300 MHz, methanol-d4) δ ppm 1.37-1.53 (m, 1H), 1.99-2.13 (m, 3H), 2.29-2.36 (m, 1H), 2.38 (s, 3H), 2.41 (s, 3H), 3.01 (dd, J=16, 5 Hz, 1H), 3.90 (t, J=6 Hz, 1H), 4.55 (d, J=4 Hz, 1H), 6.58 (d, J=8 Hz, 1H), 6.80-6.88 (m, 2H), 6.90 (d, J=9 Hz, 1H), 7.01-7.14 (m, 2H), 7.28 (s, 1H), 7.93 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 330 (M+H)+.
Sources & evidence
- ORD record
- ord-f6760457e424414295cb615b5f0b9d68
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09063126B2
Reaction notes
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