Indole-3-Carboxaldehyde → HCID 22645638, compound

HRID 2287415Notes

Reaction equation

HRID 2287415 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:5]=[C:6]([Cl:9])[C:7]=1F.[CH:14]([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([CH:14]=[O:15])=[CH:17]1

Participants

6

Reactant 3

HCID 10256Indole-3-CarboxaldehydeHCID 11430Potassium CarbonateHCID 157026Benzene, 1,3-dichloro-2-fluoro-5-(trifluoromethyl)-

Product 1

HCID 22645638HCID 22645638, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3,5-dichloro-4-fluorobenzotrifluoride (10 g) in dimethylformamide (10 ml) was added 3-formylindole (623 mg) and potassium carbonate (593 mg), the mixture was heated at 90° C. for 1.5 hrs. The reaction was cooled to room temperature and diluted with water (200 ml) and extracted with ether (200 ml). The organic fraction was separated and evaporated to dryness to give the title compound as a pale yellow crystaline material, m.p. 167-169° C.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ether (200 ml)
  3. customThe organic fraction was separated
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-170c69960ffe4d6881d51f3e2858b8b0
Source dataset
uspto-grants-2000_07
Patent number
US06083965

Reaction notes

Loading…