(2S)-1,1,1-Trifluoropropan-2-ol → 5-Chloro-3-(4-chloro-phenyl)-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine
Reaction equation
[F:1][C:2]([F:7])([F:6])[C@@H:3]([OH:5])[CH3:4].[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:12](F)=[N:13][CH:14]=1>CN(C=O)C>[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)[C:12]([O:5][C@@H:3]([CH3:4])[C:2]([F:7])([F:6])[F:1])=[N:13][CH:14]=1Participants
4
Procedure
To a mixture of 1.133 g (S)-1,1,1-trifluor-2-propanol in 10 ml dry DMF 397 mg sodium hydride (60%) was added and the mixture was stirred at room temperature for 30 minutes. The resulting solution was added dropwise at RT to a solution of 2.185 g 5-chloro-3-(4-chloro-phenyl)-2-fluoro-pyridine in 20 ml dry DMF. The reaction mixture was then stirred at room temperature for 2 h. The resulting light yellow mixture was partitioned between water and ethyl acetate, the phases were separated. The organic phase was dried over MgSO4 and purified by chromatography on silica gel with a gradient of heptane to heptane:ethyl acetate=9:1 to yield 2.330 g (76.80%) of the title compound as colorless liquid, 336.1 (M+H)+.
Workup
- additionwas added
- stirringThe reaction mixture was then stirred at room temperature for 2 h
- customThe resulting light yellow mixture was partitioned between water and ethyl acetate
- customthe phases were separated
- dry with materialThe organic phase was dried over MgSO4
- custompurified by chromatography on silica gel with a gradient of heptane to heptane
Sources & evidence
- ORD record
- ord-519f84c93e7d42569b7dd50579ade992
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090599B2
Reaction notes
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