Acetic Acid → HCID 53924420, compound
Reaction equation
[C:1](O)(=[O:3])[CH3:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:18][C:19]1[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]2[C:20]=1[CH:21]=[C:22]([C:29]([O:31][CH3:32])=[O:30])[NH:23]2>C(#N)C>[C:1]([C:21]1[C:20]2[C:24](=[C:25]([CH3:28])[CH:26]=[CH:27][C:19]=2[Cl:18])[NH:23][C:22]=1[C:29]([O:31][CH3:32])=[O:30])(=[O:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To 10 ml of anhydrous acetonitrile were added 0.74 ml (12.9 mmol) of acetic acid and 0.4 g of polyphosphoric acid. After the air in the reaction system was replaced with nitrogen, 1.86 ml (12.9 mmol) of trifluoroacetic anhydride was added and the reaction mixture was stirred at room temperature for 10 minutes. 10 ml of a solution of 1.0 g (4.3 mmol) of methyl 4-chloro-7-methylindole-2-carboxylate in acetonitrile was added dropwise over a period of 15 minutes and the reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into 100 ml of ice water and extracted with 15 ml of ethyl acetate three times. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude crystals were purified by silica gel column chromatography to provide 270 mg of white crystals. Yield: 25%
Workup
- additionwas added
- stirringthe reaction mixture was stirred at room temperature for 5 hours
- extractionextracted with 15 ml of ethyl acetate three times
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe crude crystals were purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-263d41f5536743f6a240c679be2b38f0
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05866594
Reaction notes
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