Acetyl chloride → HCID 10220777, compound
Reaction equation
[C:1]([NH:5][C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[C:22](Cl)(=[O:24])[CH3:23]>C1COCC1.O>[C:1]([NH:5][C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:22](=[O:24])[CH3:23])[CH:12]=[CH:11]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
N-tert-Butyl indole-5-carboxamide was dissolved in dry THF and solution was cooled to −78° C. Butyllithium was added dropwise with continuous stirring. The reaction mixture was stirred at −78° C. for 40 minutes followed by dropwise addition of acetyl chloride. After addition was complete, the reaction mixture was stirred at −78° C. for 30 minutes and then stirred for 1 hour at room temperature. The reaction mixture was diluted with water and organic phase separated. The aqueous phase was saturate with sodium chloride and was extracted with ethyl acetate. The extracts were combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude product was purified by column chromatrography to afford the title compound as a white solid (14.1% yield), melting point=186.8° C.
Workup
- additionAfter addition
- stirringthe reaction mixture was stirred at −78° C. for 30 minutes
- stirringstirred for 1 hour at room temperature
- customseparated
- concentrationThe aqueous phase was saturate with sodium chloride
- extractionwas extracted with ethyl acetate
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe crude product was purified by column chromatrography
Sources & evidence
- ORD record
- ord-028c304086634ccdb774e809cf13d114
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06271265B1
Reaction notes
Loading…