Chlorosulfonyl isocyanate → 6-Bromo-5-fluoro-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][C:3]=1[F:11].ClS([N:16]=[C:17]=O)(=O)=O>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:17]#[N:16])=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 6-bromo-5-fluoro-1H-indole (9.4 g, 43.9 mmol) in DMF (50 mL) at −78° C. was added chlorosulfonyl isocyanate (4.6 mL, 53 mmol). After complete addition the mixture was allowed to warm to room temperature and stir for 2 hrs. The reaction mixture was poured into ice water and stirred for 30 minutes. The precipitate was collected on a filter, washed with ice water and dried in a vacuum oven to give 6-bromo-5-fluoro-1H-indole-3-carbonitrile as a light-beige solid (10.5 g, 100%).
Workup
- additionAfter complete addition the mixture
- stirringstirred for 30 minutes
- customThe precipitate was collected on a filter
- washwashed with ice water
- customdried in a vacuum oven
Sources & evidence
- ORD record
- ord-e3d4899e65b14de1911901fe2ae5dafc
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08735414B2
Reaction notes
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