Cesium carbonate → HCID 67047885, compound

HRID 606841Notes

Reaction equation

HRID 606841 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1.[C:15]1([C:21]#[CH:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C.O.C(OCC)C.CC#N.CC#N.Cl[Pd]Cl>[Cl:14][C:12]1[CH:11]=[N:10][CH:9]=[C:8]([C:22]#[C:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 10821PhenylacetyleneHCID 171533,5-Dichloropyridine

Product 1

HCID 67047885HCID 67047885, compoundYield 16%

Reagents, catalysts & solvents 4

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Charge a Schlenk tube under a positive pressure of argon with bis(acetonitrile)palladium (II) chloride (5 mg), 2-dicyclohexylphosphinodiphenyl (21 mg), cesium carbonate (1.69 g, 5.2 mmol) and 3,5-dichloropyridine (0.3 g, 2 mmol) in acetonitrile and stir at room temperature for 25 min (Angew. Chem. Int. Ed. 42, 5993-5996, (2003)). Add phenylacetylene (0.285 mL, 2.6 mmol) and stir at 95° C. for 16 h. Dilute the reaction mixture with water and diethyl ether and separate the phases. Wash the organic layer with water, concentrate and purify the residue by silica gel chromatography, eluting with 50:50 hexanes:dichloromethane to obtain the title compound (68 mg, 16%).

Workup

  1. customseparate the phases
  2. washWash the organic layer with water
  3. concentrationconcentrate
  4. custompurify the residue by silica gel chromatography
  5. washeluting with 50:50 hexanes

Sources & evidence

ORD record
ord-07694589912f45db98389ac99738a001
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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