Water → 1-[(2-Methoxy-5-methylphenyl)sulfonyl]-1H-indole-4-carbaldehyde

HRID 1159831Notes

Reaction equation

HRID 1159831 reaction equation
[H-].[Na+].C[N:4]([CH:6]=O)[CH3:5].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[S:17](Cl)(=[O:19])=[O:18].[OH2:21]>>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[S:17]([N:4]1[C:5]2[CH:10]=[CH:11][CH:12]=[C:13]([CH:16]=[O:21])[C:14]=2[CH:15]=[CH:6]1)(=[O:19])=[O:18]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 1451496-Methoxy-m-toluenesulfonyl chloride

Product 1

HCID 866182341-[(2-Methoxy-5-methylphenyl)sulfonyl]-1H-indole-4-carbaldehyde

Procedure

To a slurry of sodium hydride (165 mg, 6.9 mmol) in DMF (5 ml) indole-4-carboxaldehyde (500 mg, 3.4 mmol) was added. The mixture was stirred for 15 min and then the 2-methoxy-5-methyl-benzenesulfonyl chloride (1140 mg, 5.2 mmol) was added and the mixture was stirred for 1 h at room temperature. Water was added and the reaction mixture was extracted with EtOAc. Evaporation gave 1.2 g. MS (ESI+) for C17H15NO4S m/z 330 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 1 h at room temperature
  2. extractionthe reaction mixture was extracted with EtOAc
  3. customEvaporation
  4. customgave 1.2 g

Sources & evidence

ORD record
ord-604b4a0a5d44483a8a5db236844ad633
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

Loading…