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

HRID 1686467ノート

反応式

HRID 1686467 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178506420bis(diphenylphosphino)ferrocene palladium(II)触媒HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-4262f872e4b94e8fa0d6b1204d141ddf
出典データセット
uspto-grants-2012_04
特許番号
US08148572B2

反応ノート

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