Cesium carbonate → 3-Trifluoromethyl-5-phenylethynylpyridine

HRID 606845

Reaction equation

HRID 606845 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1.[C:18]1([C:24]#[CH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C.O.CC#N.CC#N.Cl[Pd]Cl>[F:15][C:14]([F:17])([F:16])[C:12]1[CH:11]=[N:10][CH:9]=[C:8]([C:25]#[C:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 10821PhenylacetyleneHCID 27366983-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 670477033-Trifluoromethyl-5-phenylethynylpyridineYield 10%

Reagents, catalysts & solvents 3

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Charge a sealed tube under a positive pressure of argon with bis(acetonitrile)palladium (II) chloride (18 mg, 0.07 mmol), 2-dicyclohexylphosphino diphenyl (73 mg, 0.21 mmol), cesium carbonate (0.557 g, 1.71 mmol) and 3-chloro-5-trifluoromethylpyridine, (prepared essentially as described in PREPARATION 7), (0.12 g, 0.66 mmol) in acetonitrile and stir at room temperature for 25 min (Angew. Chem. Int. Ed. 42, 5993-5996, (2003)). Add phenylacetylene (0.1 mL, 0.86 mmol) and stir at 100° C. for 16 h. Cool to room temperature, dilute with water, and wash twice with ethyl acetate. Combine the ethyl acetate layers, dry (sodium sulfate), and concentrate. Purify the residue by silica gel chromatography, eluting with 100:0 to 50:50 hexanes:dichloromethane, to obtain the title compound (30 mg, 10%).

Workup

  1. custom(prepared essentially
  2. temperatureCool to room temperature
  3. washwash twice with ethyl acetate
  4. dry with materialdry (sodium sulfate)
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with 100:0 to 50:50 hexanes

Sources & evidence

ORD record
ord-c56a8d459fa94d37b179bea42a95c2e4
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Linked notes

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