Toluene → HCID 67400802, compound

HRID 1897981Notes

Reaction equation

HRID 1897981 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[C:11]1([C:17]2[CH:22]=[C:21](Cl)[CH:20]=[CH:19][N:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O>[C:11]1([C:17]2[CH:22]=[C:21]([C:4]3[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][CH:5]=3)[CH:20]=[CH:19][N:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 27332672-Methylphenyl boronic acidHCID 27628464-chloro-2-phenylpyridine

Product 1

HCID 67400802HCID 67400802, compoundYield 77.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 962WaterSolvent

Procedure

2-methylphenyl boronic acid (6.3 g, 46.40 mmol), 2-phenyl-4-chloropyridine (8.0 g, 42.18 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (692 mg, 1.68 mmol), and potassium phosphate tribasic (29.10 g, 126.54 mmol) 250 mL of toluene and 25 mL of water were placed in a 500 mL round-bottom flask. Nitrogen was bubbled directly into the mixture for 30 min after which tris(dibenzylideneacetone)dipalladium(0) (386 mg, 0.421 mmol) was added. Nitrogen was then bubbled for another 15 minutes then the reaction mixture was heated to reflux for 16 h under nitrogen. The mixture was cooled and the organic layer was separated from the aqueous layer. The organic layer was washed with a saturated brine solution, dried over magnesium sulfate, filtered, and the solvent removed under vacuum to give an off-white solid as the crude. The crude was purified by column chromatography using silica gel as the stationary phase and 2% ethyl acetate in hexanes as the mobile phase. 8.0 g of desired product was obtained after purification (77.4% yield).

Workup

  1. additionwas added
  2. customNitrogen was then bubbled for another 15 minutes
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for 16 h under nitrogen
  5. temperatureThe mixture was cooled
  6. customthe organic layer was separated from the aqueous layer
  7. washThe organic layer was washed with a saturated brine solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent removed under vacuum
  11. customto give an off-white solid as the crude
  12. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-c258e02d6aef49d084ecb7c47469be03
Source dataset
uspto-grants-2013_08
Patent number
US08519384B2

Reaction notes

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