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

HRID 746805Notes

Reaction equation

HRID 746805 reaction equation
[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]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl Acetate2×HCID 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-896196e551b64fc18fb134c416f5099a
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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