Potassium tert-butoxide → 4-Bromo-6-(trifluoromethyl)-1H-indole

HRID 931004Notes

Reaction equation

HRID 931004 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[C:9]([C:19]#[CH:20])=[C:10]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[NH2:11]>CN1C(=O)CCC1.C(OCC)(=O)C>[Br:7][C:8]1[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=[C:10]2[C:9]=1[CH:19]=[CH:20][NH:11]2

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 575460303-Bromo-2-ethynyl-5-(trifluoromethyl)benzenamine

Product 1

HCID 247292314-Bromo-6-(trifluoromethyl)-1H-indoleYield 69.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a solution of potassium tert-butoxide (1.33 g) in NMP (30 mL) was added a solution of 3-bromo-2-ethynyl-5-(trifluoromethyl)aniline (1.56 g) in NMP (5 mL) at 0° C., and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous ammonium chloride solution, water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (1.08 g).

Workup

  1. washwashed with saturated aqueous ammonium chloride solution, water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3f300523527b44a7b1af5fe32608213b
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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