Potassium Carbonate → HCID 44549958, compound

HRID 2382089Notes

Reaction equation

HRID 2382089 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1I)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:3][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=2)[NH:4][CH:1]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 68555340Allyl-(2-iodo-4-trifluoromethyl-phenyl)-amine

Product 1

HCID 44549958HCID 44549958, compoundYield 37.6%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of allyl-(2-iodo-4-trifluoromethyl-phenyl)-amine (1.75 g, 5.35 mmol), tetrabutylammonium chloride (1.68 g, 5.35 mmol), palladium acetate (120 mg, 0.54 mmol) and potassium carbonate (2.22 g, 16.0 mmol) in DMF (50 mL) is heated at 80° C. for 1.5 h. The reaction is quenched with water and extracted three times with DCM. The combined organic layer is dried (Na2SO4), filtered and concentrated. The residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane to afford 3-methyl-5-trifluoromethyl-1H-indole (401 mg). 1H NMR (300 MHz, CDCl3): δ=8.09 (broad s, 1H), 7.90 (s, 1 H), 7.44 (s, 1H), 7.10 (s, 1H), 2.38 (s, 3H).

Workup

  1. customThe reaction is quenched with water
  2. extractionextracted three times with DCM
  3. dry with materialThe combined organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane

Sources & evidence

ORD record
ord-087997e9c5fa424bafb481f40de183ad
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

Loading…