Cesium carbonate → HCID 67021915, compound

HRID 2198043Notes

Reaction equation

HRID 2198043 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.[OH:13][CH:14]1[CH2:18][CH2:17][NH:16][CH2:15]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>[F:8][C:5]1[CH:6]=[CH:7][C:2]([N:16]2[CH2:17][CH2:18][CH:14]([OH:13])[CH2:15]2)=[CH:3][C:4]=1[C:9]([F:12])([F:11])[F:10]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 982104-HydroxypyrrolidineHCID 634876Binap, (A+-)-HCID 27363255-Bromo-2-fluorobenzotrifluoride

Product 1

HCID 67021915HCID 67021915, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A solution of 4-bromo-1-fluoro-2-(trifluoromethyl)benzene (10 g), 3-hydroxypyrrolidine (3.56 g), palladium(II) acetate (462 mg), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (2.57 g) and cesium carbonate (26.8 g) in toluene (220 ml) was stirred under an argon gas atmosphere at 90° C. for 16 hr. After cooling to room temperature, the reaction mixture was filtered through celite, and the celite was washed with ethyl acetate. The filtrate and washing were combined and the solution was washed with water and 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 80:20-25:75) to give the title compound (5.91 g, yield 58%) as a pale-yellow oil.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. washthe celite was washed with ethyl acetate
  3. washThe filtrate and washing
  4. washthe solution was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate 80:20-25:75)

Sources & evidence

ORD record
ord-5adb94e224854ac98a130a50a4804625
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

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