Tetrahydrofuran → 5-Chloro-2-(3-chloropyridin-4-yl)-6-(trifluoromethyl)benzoxazole
Reaction equation
[Cl:1][C:2]1[CH:22]=[N:21][CH:20]=[CH:19][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=1[OH:18])=O.O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[Cl:13][C:11]1[C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]2[O:18][C:4]([C:3]3[CH:19]=[CH:20][N:21]=[CH:22][C:2]=3[Cl:1])=[N:6][C:7]=2[CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 0.67 g of 3-chloro-N-[5-chloro-2-hydroxy-4-(trifluoromethyl)phenyl]isonicotinamide, 7 ml of tetrahydrofuran and 0.55 g of triphenylphosphine, 0.91 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred for 1.5 hours. To the mixture, 0.14 g of triphenylphosphine and 0.23 g of 40% toluene solution of diethyl azodicarboxylate were added and stirred for further one hour. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the resultant crystals were washed with isopropanol and hexane to give 0.37 g of 5-chloro-2-(3-chloropyridin-4-yl)-6-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 79”).
Workup
- additionwas added dropwise at room temperature
- stirringstirred for further one hour
- concentrationThe reaction mixture was concentrated under reduced pressure
- washthe resultant crystals were washed with isopropanol and hexane
Sources & evidence
- ORD record
- ord-26e1e83cb9924ed1a100e4110798da8f
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242133B2
Reaction notes
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