{3-Bromo-5-[2-chloro-4-(ethylsulfonyl)phenoxy]phenyl}acetic acid → {3-[2-Chloro-4-(ethylsulfonyl)phenoxy]-5-pyridin-2-ylphenyl}acetic acid

HRID 1686468Notes

Reaction equation

HRID 1686468 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:21][C:22]([OH:24])=[O:23])[CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[CH:11][C:10]=2[Cl:20])[CH:7]=1.[Br-].[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Zn+]>O1CCOCC1.O.[Pd+2].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:20][C:10]1[CH:11]=[C:12]([S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])[CH:13]=[CH:14][C:9]=1[O:8][C:6]1[CH:5]=[C:4]([CH2:21][C:22]([OH:24])=[O:23])[CH:3]=[C:2]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=2)[CH:7]=1

Participants

6

Reactant 2

HCID 57791934{3-Bromo-5-[2-chloro-4-(ethylsulfonyl)phenoxy]phenyl}acetic acidHCID 178418723HCID 178418723, compound

Product 1

HCID 16123987{3-[2-Chloro-4-(ethylsulfonyl)phenoxy]-5-pyridin-2-ylphenyl}acetic acid

Reagents, catalysts & solvents 3

HCID 178506420bis(diphenylphosphino)ferrocene palladium(II)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The product from example 55 step (vi) (0.45 g), 2-pyridyl zinc bromide (0.89 ml) and bisdiphenylphosphinoferrocene palladium (II) (0.04 g) in dry dioxane (20 ml) were heated to 90° C. for 20 h. Mixture diluted with water, extracted with DCM, dried (MgSO4) and evaporated under reduced pressure to an oil, which was purified by RPHPLC to give a white solid (3 mg).

Workup

  1. extractionextracted with DCM
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure to an oil, which
  4. customwas purified by RPHPLC

Sources & evidence

ORD record
ord-d32e2f03e6a04392b263bcea98b6adad
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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