Cesium fluoride → HCID 67153507, compound

HRID 1914274Notes

Reaction equation

HRID 1914274 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F-].[Cs+]>O1CCOCC1>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=2)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 27343144-Benzyloxy-phenylboronic acid

Product 1

HCID 67153507HCID 67153507, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 2-chloro-5-trifluoromethylpyridine (1.81 g, 10 mmol), 4-benzyloxyphenyl boronic acid (2.74 g, 12 mmol) and CsF (5.32 g, 35 mmol) in dioxane (40 mL) is degassed and filled with nitrogen. PdCl2 (dppf) (200 mg) is added under nitrogen, the reaction mixture is heated at 105° C. overnight. The mixture is cooled to room temperature, diluted with ethyl acetate (100 mL), filtered through a pad of Celite. The filtrate is concentrated and the residue is purified by column chromatography on silica gel giving the title compound (2.55 g, 77.4%).

Workup

  1. customis degassed
  2. additionfilled with nitrogen
  3. additionPdCl2 (dppf) (200 mg) is added under nitrogen
  4. temperatureThe mixture is cooled to room temperature
  5. additiondiluted with ethyl acetate (100 mL)
  6. filtrationfiltered through a pad of Celite
  7. concentrationThe filtrate is concentrated
  8. customthe residue is purified by column chromatography on silica gel giving the title compound (2.55 g, 77.4%)

Sources & evidence

ORD record
ord-8c30f0e83407450297e46da2377f2811
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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