Potassium Phosphate, Tribasic → HCID 59500198, compound

HRID 1022355Notes

Reaction equation

HRID 1022355 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]=[C:22]([CH3:24])[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>[CH3:24][C:22]1[CH:21]=[CH:20][N:19]=[C:18]([C:4]2[C:5]3[O:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=[CH:2][CH:3]=2)[CH:23]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 772482-Chloro-4-methylpyridineHCID 2734328Dibenzofuran-4-boronic acid

Product 1

HCID 59500198HCID 59500198, compoundYield 90.6%

Reagents, catalysts & solvents 3

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

Procedure

4-dibenzofuranboronic acid (5.0 g, 23.6 mmol), 2-chloro-4-methylpyridine (2.6 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. 4.7 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-9ee3b9af08b74905bbb03dd4827bce8a
Source dataset
uspto-grants-2014_05
Patent number
US08722205B2

Reaction notes

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