Chlorosulfonyl isocyanate → HCID 53402097, compound

HRID 1027996Notes

Reaction equation

HRID 1027996 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

HCID 70918Chlorosulfonyl isocyanateHCID 247292425-Fluoro-6-methyl-1H-indole

Product 1

HCID 53402097HCID 53402097, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. additionAfter addition the cooling bath
  2. customwas removed
  3. additionThe mixture was then poured into ice water
  4. filtrationfiltered
  5. washwashed with water and brine
  6. dissolutionThe cake was then dissolved in acetonitrile
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1b2fbba23a09435187eb1e697cfbab1c
Source dataset
uspto-grants-2014_05
Patent number
US08735414B2

Reaction notes

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