Potassium Phosphate, Tribasic → HCID 68781555, compound

HRID 2283306Notes

Reaction equation

HRID 2283306 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][C:13]=2[S:25]([NH2:28])(=[O:27])=[O:26])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[F:29][C:30]([F:42])([F:41])[O:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1.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]>[O: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:34]3[CH:35]=[CH:36][CH:37]=[C:32]([O:31][C:30]([F:29])([F:41])[F:42])[CH:33]=3)[CH:3]=2)(=[O:10])=[O:9])=[C:13]([S:25]([NH2:28])(=[O:27])=[O:26])[CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 68782055HCID 68782055, compound

Product 1

HCID 68781555HCID 68781555, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(3-bromophenylsulfonamido)-5-phenoxybenzenesulfonamide (Example 155a) (150.0 mg, 0.31 mmol), 3-(trifluoromethoxy)benzeneboronic acid (192 mg, 0.93 mmol), tricyclohexyl phosphine (25 mg, 0.09 mmol) and potassium phosphate (131 mg, 0.62 mmol) in DMF (10 mL), was added Pd(OAc)2 (14 mg, 0.06 mmol). The reaction mixture was stirred at 80° C. overnight, 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 methanol/DCM (1:99) to afford the title compound (92 mg, 53%).

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-63a5c349ac444a0cbbde5df9981deb12
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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