Water → HCID 90240743, compound

HRID 2208636Notes

Reaction equation

HRID 2208636 reaction equation
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

Participants

7

Reactant 4

HCID 962WaterHCID 25953Cesium fluorideHCID 27606034,4,5,5-Tetramethyl-2-[4-(trifluoromethoxy)phenyl]-1,3,2-dioxaborolaneHCID 118482856HCID 118482856, compound

Product 1

HCID 90240743HCID 90240743, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  1. washthe organic phase is washed with water
  2. customdried
  3. customevaporated
  4. customThe residue is purified by chromatography on silica gel with heptane/MTB ether 2/1
  5. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-3d95b7a3b0b445a4880b4951f1d88ba0
Source dataset
uspto-grants-2016_06
Patent number
US09376622B2

Reaction notes

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