Chlorosulfonyl isocyanate → HCID 53402097, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[NH:7][CH:6]=[CH:5]2.ClS([N:16]=[C:17]=O)(=O)=O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[NH:7][CH:6]=[C:5]2[C:17]#[N:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a solution of 5-fluoro-6-methyl-1H-indole (1.9 g, 12.8 mmol) in DMF (13 mL) at −78° C. was added chlorosulfonyl isocyanate (1.33 mL, 15.3 mmol). After addition the cooling bath was removed and the mixture was allowed to warm to room temperature. The mixture was then poured into ice water, filtered and washed with water and brine. The cake was then dissolved in acetonitrile and concentrated to give 5-fluoro-6-methyl-1H-indole-3-carbonitrile (2.2 g, 100%).
Workup
- additionAfter addition the cooling bath
- customwas removed
- additionThe mixture was then poured into ice water
- filtrationfiltered
- washwashed with water and brine
- dissolutionThe cake was then dissolved in acetonitrile
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1b2fbba23a09435187eb1e697cfbab1c
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08735414B2
Reaction notes
Loading…