Potassium Phosphate, Tribasic → 5-Methyl-2-[[3-[3-(trifluoromethoxy)phenyl]phenyl]sulfonylamino]benzenesulfonamide

HRID 2283298Notes

Reaction equation

HRID 2283298 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[S:19]([NH2:22])(=[O:21])=[O:20])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[F:23][C:24]([F:36])([F:35])[O:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][S:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([O:25][C:24]([F:23])([F:35])[F:36])[CH:27]=3)[CH:3]=2)(=[O:10])=[O:9])=[C:13]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:14]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 687814742-(3-Bromobenzenesulfonylamino)-5-methyl-benzensulfonamide

Product 1

HCID 577509885-Methyl-2-[[3-[3-(trifluoromethoxy)phenyl]phenyl]sulfonylamino]benzenesulfonamideYield 30%

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 167845palladium(II) acetateCatalystHCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Pd(OAc)2 (44 mg, 0.19 mmol) was added to a solution of 2-(3-bromobenzenesulfonylamino)-5-methyl-benzensulfonamide (Example 150a) (0.40 g, 0.98 mmol), 3-(trifluoromethoxy)benzeneboronic acid (0.61 g, 2.96 mmol), tricyclohexyl phosphine (82 mg, 0.29 mmol) and potassium phosphate (0.42 g, 1.19 mmol) in toluene (10 mL). A few drops of water were added and the reaction mixture was stirred at 110° C. overnight. The reaction mixture was then diluted with 1N HCl and the product was extracted with ethyl acetate. The organic phase was separated, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash column chromatography using ethyl acetate/hexane (1:3) to afford the title compound (140 mg, 30%).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-1a06809eb1ab49b0994c63ee225b91f3
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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