Potassium Carbonate → 5-(4'-Butyl-biphenyl-4-ylsulfamoyl)-2-methyl-benzoic acid methyl ester

HRID 855987Notes

Reaction equation

HRID 855987 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:14][O:15][C:16](=[O:35])[C:17]1[CH:22]=[C:21]([S:23](=[O:33])(=[O:32])[NH:24][C:25]2[CH:30]=[CH:29][C:28](Br)=[CH:27][CH:26]=2)[CH:20]=[CH:19][C:18]=1[CH3:34].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:14][O:15][C:16](=[O:35])[C:17]1[CH:22]=[C:21]([S:23](=[O:33])(=[O:32])[NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:8]3[CH:9]=[CH:10][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:6][CH:7]=3)=[CH:27][CH:26]=2)[CH:20]=[CH:19][C:18]=1[CH3:34]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 41008604-Butylphenylboronic acidHCID 589370595-(4-Bromo-phenylsulfamoyl)-2-methyl-benzoic acid methyl ester

Product 1

HCID 589372245-(4'-Butyl-biphenyl-4-ylsulfamoyl)-2-methyl-benzoic acid methyl esterYield 64%

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 53485975CID 53485975CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-butylbenzeneboronic acid (174 mg, 0.975 mmol), 5-(4-bromo-phenylsulfamoyl)-2-methyl-benzoic acid methyl ester (150 mg, 0.39 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (16 mg, 0.019 mmol), 1,1′-bis(diphenylphosphino)ferrocene (11 mg, 0.019 mmol) and potassium carbonate (0.39 ml of a 2M aqueous solution, 0.78 mmol) in 15 ml 1,4-dioxane was heated at reflux under nitrogen for 20 hr. The reaction mixture was cooled to room temperature, diluted with 80 ml water and extracted with 2×70 ml ethyl acetate. The combined ethyl acetate extracts were washed with 60 ml brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by flash column chromatography (silica gel, 15 g), eluting with 6:1 hexane/ethyl acetate to yield the title compound as a white solid (109 mg, 64% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 20 hr
  3. extractionextracted with 2×70 ml ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with 60 ml brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash column chromatography (silica gel, 15 g)
  8. washeluting with 6:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-3ff5e21416c3424d9f6546de39707595
Source dataset
uspto-grants-2007_08
Patent number
US07262318B2

Reaction notes

Loading…