Potassium Phosphate, Tribasic → HCID 72703861, compound

HRID 918783Notes

Reaction equation

HRID 918783 reaction equation
Br[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][N:5]2[CH:14]=1.[CH2:15]([S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B1OC(C)(C)C(C)(C)O1)[CH3:16].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.O.C(OCC)(=O)C.O1CCOCC1>[CH2:15]([S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][N:5]2[CH:14]=1)[CH3:16]

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 401480152-Bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridineHCID 1237879692-(2-(Ethylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 72703861HCID 72703861, compoundYield 89.1%

Reagents, catalysts & solvents 4

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 526 mg of 2-bromo-6-trifluoromethyl-imidazo[1,2-a]pyridine, 576 mg of 2-ethylsulfanylphenylboronic acid pinacol ester, 50 mg of tris(dibenzylideneacetone) dipalladium(0), 201 mg of tricyclohexylphosphine (18% toluene solution), 1.26 g of tripotassium phosphate, 4.5 ml of 1,4-dioxane and 1.5 ml of water was stirred at 100° C. for 2.5 hours. Ethyl acetate and water were poured to the cooled reaction mixture, and the mixture was filtered. The aqueous layer of the filtrate was extracted with ethyl acetate, then combined with the organic layer of the filtrate, and the mixture was washed with water and dried over anhydrous magnesium sulfate. The mixture was concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 570 mg of 2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-imidazo[1,2-a]pyridine (hereinafter, referred to as Compound of Present Invention 4).

Workup

  1. filtrationthe mixture was filtered
  2. extractionThe aqueous layer of the filtrate was extracted with ethyl acetate
  3. washthe mixture was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1c9300ef120e4780b33c33be3ac91b33
Source dataset
uspto-grants-2016_03
Patent number
US09271500B2

Reaction notes

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