Reaktion #1005968

ord-357f2c06f93b4fbd921c673b84461cd6

Reaktionsgleichung

FC(F)(F)c1ccc2nc(Br)cn2c1
2-bromo-6-trifluoromethyl-imidazo[1,2-a]pyridine
CCSc1cc(C(F)(F)F)ccc1B1OC(C)(C)C(C)(C)O1
2-ethylsulfanyl-4-trifluoromethylphenylboronic acid pinacol ester
C1CCC(P(C2CCCCC2)C2CCCCC2)CC1
tricyclohexylphosphine
O=P([O-])([O-])[O-].[K+].[K+].[K+]
tripotassium phosphate
CCSc1cc(C(F)(F)F)ccc1-c1cn2cc(C(F)(F)F)ccc2n1
2-(2-ethylsulfanyl-4-trifluoromethylphenyl)-6-trifluoromethyl-imidazo[1,2-a]pyridine
Ausbeute 80.1%

Lösungsmittel

Reaktionsbedingungen

Temperatur
100°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionthe mixture was extracted with ethyl acetate
  2. 2
    WaschenThe organic layer was washed with water
  3. 3
    Trocknendried over anhydrous magnesium sulfate
  4. 4
    Einengenconcentrated under reduced pressure

Vorschrift

A mixture of 200 mg of 2-bromo-6-trifluoromethyl-imidazo[1,2-a]pyridine, 332 mg of 2-ethylsulfanyl-4-trifluoromethylphenylboronic acid pinacol ester, 21 mg of tris(dibenzylideneacetone) dipalladium(0), 85 mg of tricyclohexylphosphine (18% toluene solution), 480 mg of tripotassium phosphate, 1.5 ml of 1,4-dioxane and 0.5 ml of water was stirred at 100° C. for 4 hours. Water was poured to the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 236 mg of 2-(2-ethylsulfanyl-4-trifluoromethylphenyl)-6-trifluoromethyl-imidazo[1,2-a]pyridine (hereinafter, referred to as Compound of Present Invention 6).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09271500B2uspto-grants-2016_03