Dimethylformamide → 1-(2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyridin-4-yl)propan-2-ol
Reaction equation
[CH3:1][N:2]1[CH2:14][CH2:13][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[H-].[Na+].[O:17]1[CH2:19][CH:18]1[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1.[CH3:26]N(C=O)C>>[CH3:1][N:2]1[CH2:14][CH2:13][C:5]2[N:6]([CH2:19][C:18]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)([OH:17])[CH3:26])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[CH2:3]1Participants
5
Procedure
2-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (740 mg, 3.9 mmol) was dissolved in DMF and the mixture stirred for 5 min. NaH (60% in oil, 468 mg, 11.7 mmol) was added and the mixture stirred for 10 min, followed by 4-(oxiran-2-yl)pyridine (1.0 g, 7.9 mmol) and the mixture stirred at RT for 3 h. The progress of reaction was monitored by TLC. The reaction mixture was poured into ice water and filtered. The filtrate was washed with water and concentrated. The residue was recrystallized from ether to get pure product. 1HNMR (CD3OD, HCl salt) d (ppm): 8.70 (d, 2H), 8.20 (d, 2H), 7.40 (m, 1H), 7.10 (m, 1H), 7.0 (m, 2H), 4.70 (d, 1H), 4.45 (m, 2H), 4.38 (m, 1H), 3.90 (m, 1H), 3.45 (m, 2H), 3.40 (m, 1H), 3.10 (s, 3H), 1.70 (d, 3H).
Workup
- stirringthe mixture stirred for 10 min
- stirringthe mixture stirred at RT for 3 h
- customThe progress of reaction
- filtrationfiltered
- washThe filtrate was washed with water
- concentrationconcentrated
- customThe residue was recrystallized from ether
- customto get pure product
Sources & evidence
- ORD record
- ord-7046fce3202e471983e48658f731bc9d
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09255094B2
Reaction notes
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