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

HRID 907120Notes

Reaction equation

HRID 907120 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) was added dropwise a solution of ClSO2NCO (4 mL, 1.3 eq.) in acetonitrile (31 mL) at 0° C. After the addition, the mixture was stirred at room temperature for 3 h. Then it was poured into ice water and saturated NaHCO3 was added to it until it became basic. The aqueous phase was extracted with CH2Cl2 and then evaporated. The residue was 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. additionwas added to it until it
  3. extractionThe aqueous phase was extracted with CH2Cl2
  4. customevaporated
  5. customThe residue was purified with flash column chromatography on silica gel

Sources & evidence

ORD record
ord-78e2fd5c40c64073ab189e7d233932e3
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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