Potassium Phosphate, Tribasic → 6-(2-ethylsulfanylphenyl)-3-methyl-2-trifluoromethyl-3H-imidazo[4,5-b]pyridine

HRID 521681Notes

Reaction equation

[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B1OC(C)(C)C(C)(C)O1)[CH3:2].I[C:20]1[CH:21]=[C:22]2[N:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:26]([CH3:33])[C:23]2=[N:24][CH:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C(OCC)(=O)C.O1CCOCC1>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:20]1[CH:21]=[C:22]2[N:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:26]([CH3:33])[C:23]2=[N:24][CH:25]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 0.37 g of 2-ethylsulfanylphenylboronic acid pinacol ester, 0.46 g of 6-iodo-3-methyl-2-trifluoromethyl-3H-imidazo[4,5-b]pyridine, 0.03 g of tris(dibenzylideneacetone)dipalladium(0), 0.08 g of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylphenyl, 0.74 g of tripotassiurn phosphate, 0.1 ml of water and 10 ml of 1,4-dioxane was stirred at 100° C. for 4 hours. Ethyl acetate and water were added to the cooled reaction mixture, and the mixture was filtered. The filtrate was extracted with ethyl acetate and then dried over anhydrous sodium sulfate. The mixture was concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.49 g of 6-(2-ethylsulfanylphenyl)-3-methyl-2-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention 24).

Workup

filtrationthe mixture was filtered
extractionThe filtrate was extracted with ethyl acetate
dry with materialdried over anhydrous sodium sulfate
concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-77ee5a15034b42cda8a1713a638222b3
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328121B1

Reaction notes

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