Potassium Phosphate, Tribasic → HCID 58443288, compound

HRID 1630749Notes

Reaction equation

HRID 1630749 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[Cl:30][C:31]1[CH:36]=[C:35](I)[C:34]([Cl:38])=[CH:33][N:32]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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].O1CCOCC1>[Cl:30][C:31]1[CH:36]=[C:35]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[C:34]([Cl:38])=[CH:33][N:32]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27339863-Fluorophenylboronic acidHCID 534009652,5-Dichloro-4-iodopyridine

Product 1

HCID 58443288HCID 58443288, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of 3-fluorophenylboronic acid (0.776 g, 5.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.140 g, 0.15 mmol), tricyclohexylphosphine (0.087 g, 0.31 mmol), and 2,5-dichloro-4-iodopyridine 20 (1.5 g, 5.6 mmol) was added dioxane (15 mL) and a solution of potassium phosphate (2.0 g, 9.6 mmol) in water (7.5 mL). The reaction mixture was degassed by bubbling nitrogen through the solution for 10 min, and the reaction mixture was heated to 95° C. After 2 h, the reaction mixture was diluted with EtOAc, washed with water (1×), brine (1×), dried over MgSO4, filtered through a pad of silica gel (1.5 cm), and concentrated. Purification by flash column chromatography on silica gel (5% to 10% EtOAc in hexanes) gave 2,5-dichloro-4-(3-fluorophenyl)pyridine.

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling nitrogen through the solution for 10 min
  3. additionthe reaction mixture was diluted with EtOAc
  4. washwashed with water (1×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered through a pad of silica gel (1.5 cm)
  7. concentrationconcentrated
  8. customPurification by flash column chromatography on silica gel (5% to 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a9c1deb567a148e4a796b7f72bf22c16
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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