Sodium Carbonate → {5-[2-Chloro-4-(ethylsulfonyl)phenoxy]biphenyl-3-yl}acetic acid

HRID 1686467Notes

Reaction equation

HRID 1686467 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.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.Cl.[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:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 57791934{3-Bromo-5-[2-chloro-4-(ethylsulfonyl)phenoxy]phenyl}acetic acid

Product 1

HCID 57791961{5-[2-Chloro-4-(ethylsulfonyl)phenoxy]biphenyl-3-yl}acetic acidYield 51.4%

Reagents, catalysts & solvents 3

HCID 178506420bis(diphenylphosphino)ferrocene palladium(II)CatalystHCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The product from example 55 step (vi) (0.45 g), phenyl boronic acid (0.190 g), sodium carbonate (0.44 g) and bisdiphenylphosphinoferrocene palladium (II) (0.04 g) in dry dioxane (20 ml) were heated to 80° C. for 20 h. Mixture diluted with 2M HCl, extracted with ethyl acetate, dried (MgSO4) and evaporated under reduced pressure to an oil, which was purified by RPHPLC to give a cream solid (0.23 g).

Workup

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

Sources & evidence

ORD record
ord-4262f872e4b94e8fa0d6b1204d141ddf
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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