Potassium Phosphate, Tribasic → 2-[[3-(3,4-Dichlorophenyl)phenyl]sulfonylamino]-5-methyl-benzenesulfonamide

HRID 2283295Notes

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(3-bromobenzenesulfonylamino)-5-methyl-benzensulfonamide (1.50 g, 3.70 mmol), 3,4-dichlorobenzeneboronic acid (0.84 g, 4.44 mmol), tricyclohexyl phosphine (0.45 g, 1.60 mmol) and potassium phosphate (3 g, 14.15 mmol) in DMF (10 mL), was added Pd(OAc)2 (0.17 g, 0.74 mmol). The reaction mixture was stirred at 80° C. for 10 h, 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 (0.9 g, 51%).

Workup

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

Sources & evidence

ORD record: ord-d403fd88aa6b4e698772ea022a38671b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145380B2

Reaction notes

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