N,N-Dimethylaniline → HCID 11992622, compound

HRID 420826Notes

Reaction equation

HRID 420826 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[NH2:6].Br[CH2:13][C:14]([C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[CH:17]=1)=O.CN(C)C1C=CC=CC=1>CCOC(C)=O>[CH3:11][O:10][C:8]1[CH:9]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:7]=1[CH:13]=[C:14]([C:16]1[CH:17]=[C:18]([O:24][CH3:25])[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[NH:6]2

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 663013,5-DimethoxyanilineHCID 27569322-Bromo-1-(3,5-dimethoxyphenyl)ethanone

Product 1

HCID 11992622HCID 11992622, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.32 g (2.1 mmoles) of 3,5-dimethoxyaniline, 0.26 g (1.0 mmol) of 2-bromo-1-(3,5-dimethoxyphenyl)ethanone and 0.42 ml (3.3 mmol) of N,N-dimethylaniline were placed in a vial. The vial was placed inside a monomode microwave reactor and was radiated at a power of 100 W, at a temperature of 150° C. for 10 minutes. After cooling the reaction vial, the mixture was dissolved in AcOEt, was washed with an aqueous HCl 2N solution, was dried on anhydrous Na2SO4 and was evaporated at low pressure. The crude portion was purified by means of pressure column chromatography (Eluent: AcOEt/hexanes) obtaining 4,6-dimethoxy-2-(3,5-dimethoxyphenyl)-1H-indole.

Workup

  1. customThe vial was placed inside a monomode microwave reactor
  2. temperatureAfter cooling the reaction vial, the mixture
  3. washwas washed with an aqueous HCl 2N solution
  4. dry with materialwas dried on anhydrous Na2SO4
  5. customwas evaporated at low pressure
  6. customThe crude portion was purified by means of pressure column chromatography (Eluent: AcOEt/hexanes)

Sources & evidence

ORD record
ord-9bd8df5a8036493ab4bbe05e081921d1
Source dataset
uspto-grants-2012_01
Patent number
US08097656B2

Reaction notes

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