Potassium Phosphate, Tribasic → HCID 86595215, compound

HRID 1793951Notes

Reaction equation

HRID 1793951 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:15][CH2:16][NH:17][S:18]([C:21]2[CH:26]=[C:25]([C:27]#[N:28])[CH:24]=[CH:23][C:22]=2[O:29][CH3:30])(=[O:20])=[O:19])=[C:6]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=1.CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.[C:49]([O-])(=O)[CH3:50].[K+].Br[C:55]1[CH:60]=CC=C[C:56]=1[CH2:61][S:62]([CH2:65]C1C=CC=CC=1Br)(=[O:64])=[O:63].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.O.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:27]([C:25]1[CH:24]=[CH:23][C:22]([O:29][CH3:30])=[C:21]([S:18]([NH:17][CH2:16][CH2:15][C:5]2[CH:4]=[CH:3][C:2]([C:50]3[CH:49]=[CH:60][CH:55]=[CH:56][C:61]=3[S:62]([CH3:65])(=[O:64])=[O:63])=[CH:7][C:6]=2[NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:20])=[O:19])[CH:26]=1)#[N:28]

Participants

10

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 53443522HCID 53443522, compoundHCID 86595214HCID 86595214, compound

Product 1

HCID 86595215HCID 86595215, compoundYield 108.2%

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

A suspension of 0.20 g of ethyl [5-bromo-2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]phenylamino]acetate, 0.113 g of 4,4,5,5,4′,4′,5′,5′-octamethyl-2,2′-bi[[1,3,2]dioxaborolanyl], 8.8 mg of [bis(diphenylphosphino)ferrocene]dichloropalladium(II), 6.7 mg of bis(diphenylphosphino) ferrocene, and 0.118 g of potassium acetate in 3.2 mL of 1,4-dioxane was stirred under argon atmosphere at 80° C. for 20 hours. To the reaction mixture were added 94.7 mg of 2-bromophenyl(methyl)sulfone, 8.8 mg of [bis(diphenylphosphino)ferrocene]dichloropalladium(II), 257 mg of potassium phosphate, and 0.5 mL of 1,4-dioxane. After being stirred under argon atmosphere at 80° C. for 36 hours, the reaction mixture was diluted successively with ethyl acetate and water, and filtered through a diatomaceous earth column pretreated by water. The organic layer was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 0.145 g of ethyl [[4-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-2′-methanesulfonylbiphenyl-3-yl]amino]acetate.

Workup

  1. stirringAfter being stirred under argon atmosphere at 80° C. for 36 hours
  2. filtrationfiltered through a diatomaceous earth column
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0897723f6c034aca9716719a4f40bfea
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

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