Chlorosuccinimide → 1-(5-Bromo-7-chloro-2,3-dihydro-1H-indol-1-yl)ethan-1-one
Reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl:14]N1C(=O)CCC1=O>CC#N>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][C:11]=2[Cl:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
1-Acetyl-5-bromoindoline (2.47 g, 10.29 mmol) was heated at reflux with N-chlorosuccinimide (1.56 g, 10.40 mmol) in CH3CN for 30 min and an additional amount NCS (1 g, 7.47 mmol) was added while hot and the reaction was stirred at 25° C. for 16 h. The solvent was stripped in vacuo and the residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent to give 1-acetyl-5-bromo-7-chloroindoline (1.17 g).
Workup
- customthe residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent
Sources & evidence
- ORD record
- ord-897f40cda45e4c2ba32b52b451860c17
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06245769B1
Reaction notes
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