Ammonium Chloride → {4-[3,3-Bis-(4'-methanesulfonyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic Acid

HRID 9341

반응식

HRID 9341 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:24]2[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=2)=[CH:9][CH2:10][S:11][C:12]2[CH:22]=[CH:21][C:15]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[C:14]([CH3:23])[CH:13]=2)=[CH:4][CH:3]=1.[CH3:31][S:32]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)(=[O:34])=[O:33].[F-].[K+].[Cl-].[NH4+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1>[CH3:31][S:32]([C:35]1[CH:40]=[CH:39][C:38]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([C:24]3[CH:29]=[CH:28][C:27]([C:38]4[CH:39]=[CH:40][C:35]([S:32]([CH3:31])(=[O:34])=[O:33])=[CH:36][CH:37]=4)=[CH:26][CH:25]=3)=[CH:9][CH2:10][S:11][C:12]3[CH:22]=[CH:21][C:15]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[C:14]([CH3:23])[CH:13]=3)=[CH:4][CH:3]=2)=[CH:37][CH:36]=1)(=[O:34])=[O:33]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 522689Potassium FluorideHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 10370262{4-[3,3-Bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid

생성물 1

HCID 10372548{4-[3,3-Bis-(4'-methanesulfonyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic Acid

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

In an evaporated schlenk flask kept under nitrogen atmosphere were added {4-[3,3-bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid (208 mg, 0.38 mmol, example 1, step A–B), 4-(methansulfonyl)phenylboronic acid (280 mg, 1.4 mmol), KF (77 mg, 1.33 mmol), Pd2(dba)3 (21 mg, 23 mmol) and Pd(P(t-BU)3)2 (23 mg, 46 mmol). THF (5 ml) was added to the solid mixture keeping the mixture under nitrogen. The reaction mixture was stirred at room temperature for 1 h, followed by 4 h at 50° C. A saturated solution of ammonium chloride (5 ml) was added, and the mixture was extracted with dichloromethane (2×20 ml). The organic phases were dried and evaporated. The residue was purified by column chromatography (eluent: ethyl acetate:methanol (9:1)) to give the title compound in 95 mg (36%) yield.

후처리

  1. customIn an evaporated schlenk flask kept under nitrogen atmosphere
  2. waitfollowed by 4 h at 50° C
  3. extractionthe mixture was extracted with dichloromethane (2×20 ml)
  4. customThe organic phases were dried
  5. customevaporated
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate:methanol (9:1))

출처 및 근거

ORD 기록
ord-b3d87d56f4e042bca847751840000337
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091245B2

연결된 노트

불러오는 중…