Toluene → 2-Phenyl-5-(prop-1-en-2-yl)pyridine

HRID 2369738Notes

Reaction equation

HRID 2369738 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:23]1(C)[CH:28]=CC=C[CH:24]=1.CC1(C)C(C)(C)OB(C(C)=C)O1>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:8]1([C:5]2[CH:4]=[CH:3][C:2]([C:23]([CH3:28])=[CH2:24])=[CH:7][N:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 27628665-Chloro-2-phenylpyridineHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 22031701Potassium phosphate, tribasic, monohydrate

Product 1

HCID 866740462-Phenyl-5-(prop-1-en-2-yl)pyridine

Reagents, catalysts & solvents 3

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

Procedure

To a 1 L round bottom flask was added 5-chloro-2-phenylpyridine (10.15 g, 53.5 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.8 g, 4.3 mmol), potassium phosphate tribasic monohydrate (37.0 g, 161 mmol) with toluene (200 mL) and water (20 mL). The reaction mixture was degassed with nitrogen for 20 mins. 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (12.07 mL, 64.2 mmol) and Pd2(dba)3 (0.980 g, 1.070 mmol) were added and the reaction mixture was refluxed for 18 h. The aqueous layer was removed and the organic layer was concentrated to dryness. The crude product was chromatographed on silica gel with 0-20% EtOAc in hexane to yield 11 g of the desired product (HPLC purity: 95%). The product was confirmed by GC/MS.

Workup

  1. customThe reaction mixture was degassed with nitrogen for 20 mins
  2. temperaturethe reaction mixture was refluxed for 18 h
  3. customThe aqueous layer was removed
  4. concentrationthe organic layer was concentrated to dryness
  5. customThe crude product was chromatographed on silica gel with 0-20% EtOAc in hexane

Sources & evidence

ORD record
ord-271642aac05f4487b44d3be4ea80f09f
Source dataset
uspto-grants-2014_04
Patent number
US08709615B2

Reaction notes

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