3,4-dihydro-2H-pyran → 2-Acetyl-5-ethyl-7,7-dimethyl-1-(tetrahydro-pyran-2-yl)-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one
Reaction equation
[C:1]([C:4]1[NH:20][C:7]2=[CH:8][C:9]3[C:10]([CH3:19])([CH3:18])[C:11](=[O:17])[N:12]([CH2:15][CH3:16])[C:13]=3[CH:14]=[C:6]2[N:5]=1)(=[O:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:33]1[CH:38]=[CH:37][CH2:36][CH2:35][CH2:34]1>ClCCl>[C:1]([C:4]1[N:20]([CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38][O:33]2)[C:7]2=[CH:8][C:9]3[C:10]([CH3:19])([CH3:18])[C:11](=[O:17])[N:12]([CH2:15][CH3:16])[C:13]=3[CH:14]=[C:6]2[N:5]=1)(=[O:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Acetyl-5-ethyl-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (11.7 g, 43.1 mmol) and p-toluenesulfonic acid monohydrate (0.82 g, 4.3 mmol) were dissolved in dichloromethane (200 mL). To this solution 3,4-dihydro-2H-pyrane (4.81 g, 56 mmol) was added and the mixture stirred at reflux for 24 h. The mixture was filtered, the filtrate washed with water (2×100 mL), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography on silica (dichloromethane/methanol 93:3) yielding 6.8 g (44%) of a light yellow solid.
Workup
- temperatureat reflux for 24 h
- filtrationThe mixture was filtered
- washthe filtrate washed with water (2×100 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe crude product was purified by column chromatography on silica (dichloromethane/methanol 93:3)
Sources & evidence
- ORD record
- ord-70187116a86941a9925acf830b1c0e6d
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07285569B2
Reaction notes
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