1,4-Dioxane → 6-(2-Ethylsulfanylphenyl)-2-trifluoromethylimidazo[1,2-a]pyridine
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].Br[C:20]1[CH:21]=[CH:22][C:23]2[N:24]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=2)[CH:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>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>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:20]1[CH:21]=[CH:22][C:23]2[N:24]([CH:26]=[C:27]([C:29]([F:31])([F:32])[F:30])[N:28]=2)[CH:25]=1)[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 110 °C
Procedure
A mixture of 0.53 g of 2-ethylsulfanylphenylboronic acid pinacol ester, 0.52 g of 6-bromo-2-trifluoromethylimidazo[1,2-a]pyridine, 0.02 g of tris(dibenzylideneacetone)dipalladium(0), 0.05 g of 2-dicyclohexylphosphino-2′,6′-dimethoxyphenyl, 0.84 g of tripotassium phosphate and 6 ml of 1,4-dioxane was stirred at 110° C. for 7 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 0.28 g of 6-(2-ethylsulfanylphenyl)-2-trifluoromethylimidazo[1,2-a]pyridine (Compound of Present Invention 26).
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-5460b4dd5ede4b9ea643e13bc7c9d40a
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328121B1
Reaction notes
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