2-Chloropyridine → HCID 59500175, compound

HRID 1022351Notes

Reaction equation

HRID 1022351 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4](B(O)O)=[CH:3][CH:2]=1.Cl[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 79772-ChloropyridineHCID 62657Potassium Phosphate, TribasicHCID 2734328Dibenzofuran-4-boronic acid

Product 1

HCID 59500175HCID 59500175, compoundYield 91.7%

Reagents, catalysts & solvents 3

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4-dibenzofuranboronic acid (5.0 g, 23.6 mmol), 2-chloropyridine (2.2 g, 20 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (S-Phos) (0.36 g, 0.8 mmol), and potassium phosphate (11.4 g, 50 mmol) were mixed in 100 mL of toluene and 10 mL of water. Nitrogen is bubbled directly into the mixture for 30 minutes. Next, Pd2(dba)3 was added (0.18 g, 0.2 mmol) and the mixture was heated to reflux under nitrogen for 8 h. The mixture was cooled and the organic layer was separated. The organic layers are washed with brine, dried over magnesium sulfate, filtered, and evaporated to a residue. The residue was purified by column chromatography eluting with dichloromethane. 4.5 g of desired product was obtained after purification.

Workup

  1. customNitrogen is bubbled directly into the mixture for 30 minutes
  2. additionNext, Pd2(dba)3 was added (0.18 g, 0.2 mmol)
  3. temperaturethe mixture was heated
  4. temperatureto reflux under nitrogen for 8 h
  5. temperatureThe mixture was cooled
  6. customthe organic layer was separated
  7. washThe organic layers are washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated to a residue
  11. customThe residue was purified by column chromatography
  12. washeluting with dichloromethane

Sources & evidence

ORD record
ord-7f0f7fca3c4f4f278960eeca11358541
Source dataset
uspto-grants-2014_05
Patent number
US08722205B2

Reaction notes

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