Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][N:9]=2)=[CH:4][C:3]=1[F:17].CC1(C)C(C)(C)OB([C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=2)O1.[F-].[Cs+].O>O1CCOCC1.CCOCC>[F:17][C:3]1[CH:4]=[C:5]([C:8]2[N:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][N:9]=2)[CH:6]=[N:7][C:2]=1[C:26]1[CH:27]=[CH:28][C:29]([O:32][C:33]([F:34])([F:35])[F:36])=[CH:30][CH:31]=1
10.2 mmol of 2-(6-chloro-5-fluoropyridin-3-yl)-5-propylpyrimidine and 10.2 mmol of 4,4,5,5-tetramethyl-2-(4-trifluoromethoxyphenyl)-1,3,2-dioxaborolane are dissolved in 30 ml of dioxane, and 20.4 mmol of caesium fluoride and 0.5 mmol of bis(tricyclohexylphosphine)palladium dichloride catalyst are added. The mixture is heated at 100° C. for 18 hours with stirring. Water and MTB ether are added to the batch, and the organic phase is washed with water, dried using sodium sulfate and evaporated. The residue is purified by chromatography on silica gel with heptane/MTB ether 2/1 and recrystallised from isopropanol, giving 2-[5-fluoro-6-(4-trifluoromethoxyphenyl)pyridin-3-yl]-5-propylpyrimidine.
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