Triethylamine → 5-Methylsulfanyl-3''-(propane-2-sulfonylamino)-[1,1';4',1'']terphenyl-2-carboxylic acid methyl ester

HRID 746805노트

반응식

HRID 746805 반응식
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([S:10][CH3:11])=[CH:6][C:5]=1OS(C(F)(F)F)(=O)=O.[CH3:21][C:22]1([CH3:29])[C:26]([CH3:28])([CH3:27])OBO1.CCN([CH2:35][CH3:36])CC.BrC1C=C[C:41]([C:44]2C=CC=C[C:45]=2[NH:50][S:51]([CH:54]([CH3:56])[CH3:55])(=[O:53])=[O:52])=CC=1.[CH3:57]COC(C)=O>CCOC(C)=O.CCCCCC.O1CCOCC1.C(#N)C>[CH3:1][O:2][C:3]([C:4]1[C:5]([C:35]2[CH:36]=[CH:29][C:22]([C:26]3[CH:28]=[CH:41][CH:44]=[C:45]([NH:50][S:51]([CH:54]([CH3:56])[CH3:55])(=[O:53])=[O:52])[CH:27]=3)=[CH:21][CH:57]=2)=[CH:6][C:7]([S:10][CH3:11])=[CH:8][CH:9]=1)=[O:20]

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 8857Ethyl Acetate2회HCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 57974945N-(4'-bromo-[1,1'-biphenyl]-2-yl)propane-2-sulfonamideHCID 866131664-Methylsulfanyl-2-trifluoromethanesulfonyloxy-benzoic acid methyl ester

생성물 1

HCID 692524875-Methylsulfanyl-3''-(propane-2-sulfonylamino)-[1,1';4',1'']terphenyl-2-carboxylic acid methyl ester수율 63%

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 312751,4-Dioxane용매HCID 21226206Ethyl acetate hexane용매

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온도
80 °C

실험 절차

Mix 4-Methylsulfanyl-2-trifluoromethanesulfonyloxy-benzoic acid methyl ester (1.216 g, 3.682 mmol), 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (0.85 ml, 5.682 ), Et3N (1.55 ml, 11.121 mmol) and acetonitrile (40 ml) then heat to reflux for 16 hours. Dilute the reaction with EtOAc and wash with water. Concentrate under reduced pressure. Next add propane-2-sulfonic acid (4′-bromo-biphenyl-2-yl)-amide (0.532 g, 1.502 mmol) 2N Na2CO3 (7 ml, 14 mmol), 1,4-dioxane (35 ml) and tetrakis triphenyl phosphine palladium (0.177 g, 0.153 mmol). Heat to 80° C. for 16 hours. Cool the reaction, dilute with EtOAc, and wash with H2O, followed by saturated aqueous sodium chloride. Dry with Na2SO4 and concentrate under reduced pressure. Purify the reaction by flash chromatography (Silica gel-toluene then up to 20% EtOAc/Hexane) to give 5-Methylsulfanyl-3″-(propane-2-sulfonylamino)-[1,1′;4′,1″]terphenyl-2-carboxylic acid methyl ester (0.431 g, 63%). MS (m/e): 456(M+1).

후처리

  1. temperaturethen heat
  2. temperatureto reflux for 16 hours
  3. additionDilute
  4. washwash with water
  5. concentrationConcentrate under reduced pressure
  6. temperatureCool
  7. customthe reaction
  8. washwash with H2O
  9. dry with materialDry with Na2SO4
  10. concentrationconcentrate under reduced pressure
  11. customPurify
  12. customthe reaction by flash chromatography (Silica gel-toluene

출처 및 근거

ORD 기록
ord-896196e551b64fc18fb134c416f5099a
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393868B2

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