Cesium carbonate → HCID 68822444, compound

HRID 238304Notes

Reaction equation

HRID 238304 reaction equation
[CH3:1][O:2][C:3](=[O:13])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[N:8][C:9](Br)=[CH:10][CH:11]=1.[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3](=[O:13])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[N:8][C:9]([C:18]2[CH:17]=[CH:16][C:15]([F:14])=[CH:20][C:19]=2[F:21])=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 27343342,4-Difluorophenylboronic acidHCID 86621313HCID 86621313, compound

Product 1

HCID 68822444HCID 68822444, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1.0 g (4.13 mmol) of (E)-3-(6-bromopyridin-3-yl)acrylic acid methyl ester, 782.8 mg (4.95 mmol) of 2,4-difluorophenylboronic acid, 108.4 mg (0.413 mmol) of triphenylphosphane, 46.38 mg (0.2 mmol) of palladium(II)acetate and 1.75 g (5.37 mmol) of cesium carbonate were stirred in 40 ml of dioxane and 15 ml water under argon at 100° C. for 6 h. The mixture was filtered, evaporated and the residue dissolved in methanol. By treatment with thionyl chloride the partially saponified methyl ester was re-esterified. After evaporation, the crude product was purified by chromatography (RP18, acetonitrile/water containing 0.1% TFA). Yield: 434 mg (25%).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. dissolutionthe residue dissolved in methanol
  4. customAfter evaporation
  5. customthe crude product was purified by chromatography (RP18, acetonitrile/water containing 0.1% TFA)

Sources & evidence

ORD record
ord-974118f8a9c94be1badb809b7e08a315
Source dataset
uspto-grants-2014_02
Patent number
US08642620B2

Reaction notes

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