Trifluoroacetic anhydride → 5-Chloro-6-(2-dimethylaminoethoxy)-1H-indole

HRID 399265Notes

Reaction equation

HRID 399265 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([O:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[CH:7]=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+]>C(O)(C(F)(F)F)=O.CO>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[NH:5][CH:4]=[CH:3]2

Participants

6

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 11430Potassium CarbonateHCID 57027129N-[4-Chloro-3-(2-dimethylaminoethoxy)phenyl]aminoacetaldehyde dimethyl acetal

Product 1

HCID 540864225-Chloro-6-(2-dimethylaminoethoxy)-1H-indoleYield 77.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

A solution of N-[4-chloro-3-(2-dimethylaminoethoxy)phenyl]aminoacetaldehyde dimethyl acetal (D7, 0.61 g, 0.002 mol) in TFA (2.6 ml) at 0° C., was treated with TFAA (2.6 ml) under an argon atmosphere. More TFA (3.7 ml ) was added and the reaction was heated to reflux for 48 h. The solution was evaporated to dryness and the residue taken up in EtOAc. The extract was dried (Na2SO4) and concentrated in vacuo to leave a brown oil which was dissolved in MeOH (10 ml), treated with K2CO3 (1 g) and then stirred at room temperature for 3 h The mixture was concentrated in vacuo, and then the residue treated with water and extracted with EtOAc. The solution was dried (Na2SO4) and concentrated in vacuo to give the title compound as a brown solid (0.37 g , 76%)

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 48 h
  3. customThe solution was evaporated to dryness
  4. dry with materialThe extract was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto leave a brown oil which
  7. concentrationwas concentrated in vacuo
  8. additionthe residue treated with water
  9. extractionextracted with EtOAc
  10. dry with materialThe solution was dried (Na2SO4)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9226eaef93244376b2c927ac898b39ae
Source dataset
uspto-grants-1998_10
Patent number
US05817833

Reaction notes

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