Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].[Cl-].[C:20](#[N:22])[CH3:21]>CN(C)C=O>[C:20]([CH2:21][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[CH:7]=[C:8]1[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:22]Participants
5
Procedure
Under nitrogen, dissolve 2.15 g of ethyl 6-methoxy-1H-indole-2-carboxylate in 10 ml of dimethylformamide. Add 0.59 g of sodium hydride in small portions at 0° C. and stir the reaction at 0° C. for 30 minutes. Add 0.93 ml of acetonitrile chloride at 0° C. and stir the reaction at ambient temperature for 24 hours. Add water and extract with ethyl acetate. Wash the organic phase with saturated aqueous sodium hydrogen carbonate solution and with saturated aqueous sodium chloride solution. Dry the organic phase over sodium sulfate, filter and evaporate. Purify the compound by column chromatography on silica gel using dichloromethane as eluant. The title compound is obtained in the form of a white powder.
Workup
- customthe reaction at 0° C. for 30 minutes
- stirringstir
- customthe reaction at ambient temperature for 24 hours
- extractionAdd water and extract with ethyl acetate
- washWash the organic phase with saturated aqueous sodium hydrogen carbonate solution
- dry with materialDry the organic phase over sodium sulfate
- filtrationfilter
- customevaporate
- customPurify the compound by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-52cb79800106468da5f87f8a9544c8a8
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003682B2
Linked notes
Loading…