Potassium Carbonate → N-{2-(methyloxy)-5-[3-(4-{[2-(methyloxy)phenyl]sulfonyl}-1-piperazinyl)-6-quinoxalinyl]-3-pyridinyl}cyclopropanesulfonamide

HRID 734979Notes

Reaction equation

HRID 734979 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([N:12]3[CH2:17][CH2:16][N:15]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])(=[O:20])=[O:19])[CH2:14][CH2:13]3)=[N:9]2)=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].Br[C:53]1[CH:54]=[C:55]([NH:61][S:62]([CH:65]2[CH2:67][CH2:66]2)(=[O:64])=[O:63])[C:56]([O:59][CH3:60])=[N:57][CH:58]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:60][O:59][C:56]1[C:55]([NH:61][S:62]([CH:65]2[CH2:66][CH2:67]2)(=[O:63])=[O:64])=[CH:54][C:53]([C:2]2[CH:11]=[C:10]3[C:5](=[CH:4][CH:3]=2)[N:6]=[CH:7][C:8]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])(=[O:20])=[O:19])[CH2:14][CH2:13]2)=[N:9]3)=[CH:58][N:57]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 57843318N-(5-Bromo-2-methoxypyridin-3-yl)cyclopropanesulfonamideHCID 685015527-Bromo-2-(4-{[2-(methyloxy)phenyl]sulfonyl}-1-piperazinyl)quinoxaline

Product 1

HCID 57843407N-{2-(methyloxy)-5-[3-(4-{[2-(methyloxy)phenyl]sulfonyl}-1-piperazinyl)-6-quinoxalinyl]-3-pyridinyl}cyclopropanesulfonamideYield 38%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A slurry of 7-bromo-2-(4-{[2-(methyloxy)phenyl]sulfonyl}-1-piperazinyl)quinoxaline (0.54 mmol), bis(pinacolato)diboron (0.81 mmol), potassium acetate (2.15 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.05 mmol) in 1,4-dioxane (4 ml) was heated at 100° C. After the reaction stirred for 1 hour, N-[5-bromo-2-(methyloxy)-3-pyridinyl]cyclopropanesulfonamide (0.81 mmol) and 2M solution potassium carbonate (2 ml) was added and continued to stir for 1 hour. The reaction was cooled to ambient temperature, separated the organic layer and purified directly on silica by column chromatography (30-100% ethyl acetate/hexanes). The desired fractions were combined and concentrated to give the title compound (125 mg, 38% yield) as a pale tan solid. MS(ES)+ m/e 611.2 [M+H]+.

Workup

  1. stirringto stir for 1 hour
  2. customseparated the organic layer
  3. custompurified directly on silica by column chromatography (30-100% ethyl acetate/hexanes)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e80c496dbd144289b5a0811a7904a78a
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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