2-Methylindole → HCID 15549845, compound

HRID 275783Notes

Reaction equation

HRID 275783 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.CC(C)([O-])C.[K+].F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>CS(C)=O.O>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:10]=[C:2]2[CH3:1])=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

6

Reactant 3

HCID 72242-MethylindoleHCID 9590p-FluoronitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 15549845HCID 15549845, compoundYield 26.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-methylindol (1 g, 7.6 mmol) and potassium t-butoxide (897 mg, 8 mmol) in DMSO (10 mL) was stirred at room temperature under argon for 30 min. 4-Fluoronitrobenzene (0.81 mL, 7.62 mmol) was added and the reaction mixture was heated to 100° C. in an oil bath for 5 h. The reaction mixture was diluted with water, extracted with EtOAc, the organic extract with washed with water and dried (MgSO4). The oil obtained on concentration was flash chromatographed on silica gel and elution was -carried out with a gradient of 5-8% EtOAc in hexane to give 1-(4-nitrophenyl)-2-methylindol (500 mg).

Workup

  1. extractionextracted with EtOAc
  2. extractionthe organic extract
  3. washwith washed with water
  4. dry with materialdried (MgSO4)
  5. customThe oil obtained on concentration
  6. customchromatographed on silica gel and elution

Sources & evidence

ORD record
ord-14b06517545d4a6d9c29487a417f040b
Source dataset
uspto-grants-2002_03
Patent number
US06353007B1

Reaction notes

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