Chlorosulfonyl isocyanate → 6-methoxy-2-methyl-1H-indole-3-carbonitrile

HRID 252513Notes

Reaction equation

HRID 252513 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([CH3:12])[NH:9]2)=[CH:5][CH:4]=1.ClS([N:17]=[C:18]=O)(=O)=O.C([O-])(O)=O.[Na+]>C(#N)C.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:18]#[N:17])=[C:8]([CH3:12])[NH:9]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 108447096-methoxy-2-methyl-1H-indole

Product 1

HCID 139046406-methoxy-2-methyl-1H-indole-3-carbonitrileYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 6-methoxy-2-methyl-1H-indole (3.9 g, 24 mmol) in acetonitrile (200 mL) and DMF (20 mL) is added dropwise a solution of ClSO2NCO (4 mL, 1.3 eq.) in acetonitrile (31 mL) at 0° C. After the addition, the mixture is stirred at room temperature for 3 h. Then it is poured into ice water and saturated NaHCO3 is added to it until it becomes basic. The aqueous phase is extracted with CH2Cl2 and then evaporated. The residue is purified with flash column chromatography on silica gel using EtOAc/petroleum ether (1/5) as eluent to yield 81% of 6-methoxy-2-methyl-1H-indole-3-carbonitrile.

Workup

  1. additionAfter the addition
  2. additionis added to it until it
  3. extractionThe aqueous phase is extracted with CH2Cl2
  4. customevaporated
  5. customThe residue is purified with flash column chromatography on silica gel

Sources & evidence

ORD record
ord-a3b2adcd5e7a4039b8a70e9d60a9474a
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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