Cesium carbonate → HCID 86658338, compound

HRID 2198033Notes

Reaction equation

HRID 2198033 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1Br.[OH:16][CH:17]1[CH2:21][CH2:20][NH:19][CH2:18]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[N:19]1[CH2:20][CH2:21][CH:17]([OH:16])[CH2:18]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 982104-HydroxypyrrolidineHCID 634876Binap, (A+-)-HCID 27347632,5-Bis(trifluoromethyl)bromobenzene

Product 1

HCID 86658338HCID 86658338, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 2,5-bis(trifluoromethyl)phenyl bromide (4.45 g), 3-hydroxypyrrolidine (1.2 g), palladium(II) acetate (0.16 g), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.87 g) and cesium carbonate (13.6 g) in toluene (74 mL) was stirred under an argon gas atmosphere at 80° C. for 16 hr. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate 90:10-75:25) to give the title compound (3.79 g, yield 91%) as an orange oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate 90:10-75:25)

Sources & evidence

ORD record
ord-2a41ef61ab174745bb2c53c77dbfae65
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

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