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

HRID 1686467노트

반응식

HRID 1686467 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178506420bis(diphenylphosphino)ferrocene palladium(II)촉매HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-4262f872e4b94e8fa0d6b1204d141ddf
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148572B2

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