Chlorosulfonyl isocyanate → 6-Bromo-5-fluoro-1H-indole-3-carbonitrile

HRID 1028002Notes

Reaction equation

HRID 1028002 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

HCID 70918Chlorosulfonyl isocyanateHCID 222629226-Bromo-5-fluoroindole

Product 1

HCID 534029576-Bromo-5-fluoro-1H-indole-3-carbonitrileYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. additionAfter complete addition the mixture
  2. stirringstirred for 30 minutes
  3. customThe precipitate was collected on a filter
  4. washwashed with ice water
  5. 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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