Potassium Phosphate, Tribasic → HCID 117922170, compound

HRID 594197Notes

Reaction equation

HRID 594197 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1.[F:15][C:16]([F:27])([F:26])[C:17]1[N:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[N+:8]([C:7]1[C:2]([C:20]2[CH:21]=[N:22][C:17]([C:16]([F:27])([F:26])[F:15])=[CH:18][CH:19]=2)=[N:3][CH:4]=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)([O-:10])=[O:9]

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 47369502-Chloro-3-nitro-5-(trifluoromethyl)pyridineHCID 251342782-(Trifluoromethyl)pyridine-5-boronic Acid

Product 1

HCID 117922170HCID 117922170, compoundYield 77.3%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

Under an argon atmosphere, to a solution of 2-chloro-3-nitro-5-(trifluoromethyl)pyridine (1 g) in 1,4-dioxane (15 mL) were added (6-(trifluoromethyl)pyridin-3-yl)boronic acid (925 mg), a solution of tricyclohexylphosphine in 15% toluene (2.0 mL), tris(dibenzylideneacetone)dipalladium (2.02 g) and a tripotassium phosphate aqueous solution (2 mol/L, 5.9 mL) and stirred overnight at 90° C. The reaction mixture was added with water and filtered through Celite® and the filtrate was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified on silica gel column chromatography (hexane:ethyl acetate=85:15) to give the titled compound (1.15 g) having the following physical data.

Workup

  1. filtrationfiltered through Celite®
  2. extractionthe filtrate was extracted with ethyl acetate
  3. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified on silica gel column chromatography (hexane:ethyl acetate=85:15)

Sources & evidence

ORD record
ord-4c58c6beedff43bdb3ca041f578eb839
Source dataset
uspto-grants-2016_01
Patent number
US09242977B2

Reaction notes

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