Potassium Phosphate, Tribasic → HCID 67396524, compound

HRID 714642Notes

Reaction equation

HRID 714642 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.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]>[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 38477682-Bromo-isonicotinic acid methyl ester

Product 1

HCID 67396524HCID 67396524, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Under an atmosphere of argon, 500 mg (2.31 mmol) of methyl 2-bromoisonicotinate and 694 mg (3.47 mmol) of 2-(trifluoromethyl)phenylboronic acid were dissolved in 10 ml of toluene. 106 mg (0.12 mmol) of tris(dibenzylideneacetone)dipalladium, 91 mg (0.23 mmol) of tri-tert-butylphosphine and 982 mg (4.63 mmol) of potassium phosphate were then added, and under argon the mixture was heated to 110° C. for 20 h. For work-up, the mixture was diluted at RT with 15 ml of ethyl acetate and 15 ml of water, the organic phase was separated off and the aqueous phase was extracted two more times with in each case 15 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1, then 10:1). This gave 498 mg (59% of theory) of the target compound in a purity of 77%. A second product fraction of lower purity was purified further according to Method 19. This gave a further 54 mg (8% of theory) of the target compound.

Workup

  1. customthe organic phase was separated off
  2. extractionthe aqueous phase was extracted two more times with in each case 15 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by chromatography on silica gel (mobile phase
  7. customA second product fraction of lower purity was purified further
  8. customThis gave a further 54 mg (8% of theory) of the target compound

Sources & evidence

ORD record
ord-60cff971570744bbb53d186dc6681285
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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