Potassium Phosphate, Tribasic → HCID 86674045, compound

HRID 713562Notes

Reaction equation

HRID 713562 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:22][C:23]1(C)[C:27](C)(C)OB(C(C)=C)O1>C1(C)C=CC=CC=1.O.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].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[C:8]1([C:4]2[CH:3]=[C:2]([C:23]([CH3:27])=[CH2:22])[CH:7]=[CH:6][N:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27628464-chloro-2-phenylpyridineHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane

Product 1

HCID 86674045HCID 86674045, compoundYield 93.7%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

4-Chloro-2-phenylpyridine (14 g, 73.8 mmol) and potassium phosphate (51.0 g, 221 mmol) were dissolved in 300 mL of toluene and 30 mL of water. The reaction was purged with nitrogen for 20 minutes and then 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (16.65 mL, 89 mmol), Pd2(dba)3 (1.35 g, 1.48 mmol) and S-Phos (2.42 g, 5.91 mmol) were added. The reaction was brought to reflux for 18 h. After cooling, 100 mL of water was added, separated and the aqueous layer extracted twice with 100 mL of ethyl acetate. The organic layers were passed through a plug of silica gel, eluting with DCM. After evaporation of the solvent, the crude product was subjected to column chromatography (SiO2, 5% EtOAc in hexane to 10% EtOAc in hexane) to get 13.5 g (90%) of 2-phenyl-4-(prop-1-en-2yl)pyridine.

Workup

  1. customThe reaction was purged with nitrogen for 20 minutes
  2. temperatureto reflux for 18 h
  3. temperatureAfter cooling
  4. customseparated
  5. extractionthe aqueous layer extracted twice with 100 mL of ethyl acetate
  6. washeluting with DCM
  7. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-9e85a2c18d8649a0b47b1a4c43001ad5
Source dataset
uspto-grants-2015_11
Patent number
US09184397B2

Reaction notes

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