Potassium Carbonate → HCID 18629512, compound

HRID 1872824Notes

Reaction equation

HRID 1872824 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)=[CH2:15].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]([C:14]#[CH:15])=[CH:17]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 157026Benzene, 1,3-dichloro-2-fluoro-5-(trifluoromethyl)-HCID 145324453-Ethenyl-1H-indole

Product 1

HCID 18629512HCID 18629512, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3,5-dichloro-4-fluorobenzotrifluoride (4.79 g) in dimethylformamide (25 ml) was added 3-ethenylindole (2.9 g) and potassium carbonate (2.84 g), the mixture was heated at 90° C. for 3 hours under an atmosphere of nitrogen and then left to stir overnight at room temperature. The reaction was diluted with water (100 ml) and extracted with hexane (2×100ml). The organic fractions were separated, combined, evaporated to dryness and purified by column chromatography on silica gel (300 g) eluted with hexane:ethylacetate (97:3) to give the title compound as a white solid (1.3 g), m.p. 120-122 ° C.

Workup

  1. waitleft
  2. extractionextracted with hexane (2×100ml)
  3. customThe organic fractions were separated
  4. customevaporated to dryness
  5. custompurified by column chromatography on silica gel (300 g)
  6. washeluted with hexane:ethylacetate (97:3)

Sources & evidence

ORD record
ord-e82ad416317748ffb112a3984ded67bc
Source dataset
uspto-grants-2000_08
Patent number
US06110958

Reaction notes

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