Potassium Phosphate, Tribasic → HCID 72703864, compound

HRID 918786Notes

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]=[C:22]([C:24]([F:27])([F:26])[F:25])[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.O1CCOCC1>[CH2:15]([S:17][C:18]1[CH:23]=[C:22]([C:24]([F:26])([F:25])[F:27])[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

Conditions

Temperature: 100 °C

Procedure

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).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-357f2c06f93b4fbd921c673b84461cd6
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09271500B2

Reaction notes

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