Chlorosulfonyl isocyanate → 6-Bromo-1H-indole-3-carbonitrile
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.ClS([N:15]=[C:16]=O)(=O)=O>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16]#[N:15])=[CH:7][NH:8]2)=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 6-bromo-1H-indole (41.36 g, 211.0 mmol) in DMF (150 mL) at −78° C. was added chlorosulfonyl isocyanate (20 mL, 225 mmol). After complete addition, the mixture was allowed to warm to room temperature and stirred for 2 hrs. The reaction mixture was poured into ice (500 mL) and stirred for 30 minutes. The precipitate was collected on a filter and dried in a vacuum oven to give 6-bromo-1H-indole-3-carbonitrile as a light-beige solid (46.73 g, 100%).
Workup
- additionAfter complete addition
- stirringstirred for 30 minutes
- customThe precipitate was collected on
- filtrationa filter
- customdried in a vacuum oven
Sources & evidence
- ORD record
- ord-eadf67fb14f44d17b7dba449aee1e58d
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08735414B2
Reaction notes
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