3-(Dimethylaminomethyl)-7-azaindole → HCID 21462989, compound
Reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH:11]=[CH:10]3)[CH2:3][CH2:2]1.CN([CH2:19][C:20]1[C:28]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)C>>[NH:12]1[C:13]2[C:9](=[CH:8][C:7]([C:4]3[CH2:3][CH2:2][N:1]([CH2:19][C:20]4[C:28]5[C:23](=[N:24][CH:25]=[CH:26][CH:27]=5)[NH:22][CH:21]=4)[CH2:6][CH:5]=3)=[CH:15][CH:14]=2)[CH:10]=[CH:11]1Participants
Procedure
5-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole (200 mg, 1.0 mmol) and 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (177 mg, 1.01 mmol) were coupled as described in Example 4 to give a solid which was purified by flash chromatography, eluting with 10% methanol in dichloromethane containing 1% ammonia. Recrystallisation from methanol gave the title compound (115 mg, 35%) as a tan solid, m.p. 187°-189° C.; (Found: C, 73.78; H, 6.34; N, 16.13. C21H20N4.0.75 H2O requires C, 73.77; H, 6.34; N, 16.39%); δH (DMSO-d6) 2.68 (2H, m, tetrahydropyridinyl H), 3.10 (2H, s, tetrahydropyridinyl H), 3.18 (1H, d, J 4.4 Hz, tetrahydropyridinyl H), (other tetrahydropyridinyl H obscured by solvent at 3.30), 3.74 (2H, s, ArCH2N), 6.02 (1H, m, CH=CR), 6.40 (1H, s, ArH), 7.04 (1H, dd, J 7.5, 3.2 Hz, 5-H), 7.20 (1H, d, J 8.2 Hz, ArH), 7.32 (2H, m, ArH), 7.40 (1H, s, ArH), 7.52 (1H, s, ArH), 8.04 (1H, d, J 7.5 Hz, 4-H), 8.18 (1H, d, J 3.2 Hz, 6-H), 11.00 (1H, br s, NH), and 11.48 (1H, br s, NH); m/z (CI+, NH3) 329 (M+1)+.
Workup
- customto give a solid which
- customwas purified by flash chromatography
- washeluting with 10% methanol in dichloromethane containing 1% ammonia
- customRecrystallisation from methanol
Sources & evidence
- ORD record
- ord-e8f703b1fe9c4fbba1b6654ecb9d4642
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05700809
Reaction notes
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