Potassium Carbonate → HCID 24804676, compound

HRID 1667636Notes

Reaction equation

HRID 1667636 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[CH2:16][C:17]([OH:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:20][C:21]([F:33])([F:32])[O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:26]2[CH:25]=[CH:24][C:23]([O:22][C:21]([F:20])([F:32])[F:33])=[CH:28][CH:27]=2)=[CH:11][C:10]=1[CH2:16][C:17]([OH:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 33070112-[2-(Benzyloxy)-5-bromophenyl]acetic acid

Product 1

HCID 24804676HCID 24804676, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-benzyloxy-5-bromophenylacetic acid (261 mg, 0.813 mmol), 4-(trifluoromethoxy)phenyl boronic acid (218 mg, 1.056 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (43 mg, 0.057 mmol), potassium carbonate (169 mg, 1.22 mmol), dioxane (4 ml) and water (0.5 ml) was stirred at 80° C. for 2 hours. The reaction mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, and the solution was filtered through celite. The residue obtained by concentration of the filtrate under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:2) to give the title compound (160 mg, 48.9%) as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. filtrationthe solution was filtered through celite
  5. customThe residue obtained by concentration of the filtrate under reduced pressure
  6. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-e4c22962861d4369a18d15a21b4133ec
Source dataset
uspto-grants-2011_10
Patent number
US08044236B2

Reaction notes

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