Potassium Carbonate → N-(5-{3-[(1-methyl-1H-pyrazol-3-yl)amino]-6-quinoxalinyl}-3-pyridinyl)benzenesulfonamide

HRID 734970Notes

Reaction equation

HRID 734970 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([NH:12][C:13]3[CH:17]=[CH:16][N:15]([CH3:18])[N:14]=3)=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[C:29]([NH:33][S:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)(=[O:36])=[O:35])[CH:30]=[N:31][CH:32]=2)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:18][N:15]1[CH:16]=[CH:17][C:13]([NH:12][C:8]2[CH:7]=[N:6][C:5]3[C:10]([N:9]=2)=[CH:11][C:2]([C:27]2[CH:28]=[C:29]([NH:33][S:34]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)(=[O:35])=[O:36])[CH:30]=[N:31][CH:32]=2)=[CH:3][CH:4]=3)=[N:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 52936632N-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]benzenesulfonamideHCID 685082717-bromo-N-(1-methyl-1H-pyrazol-3-yl)-2-quinoxalinamine

Product 1

HCID 57843502N-(5-{3-[(1-methyl-1H-pyrazol-3-yl)amino]-6-quinoxalinyl}-3-pyridinyl)benzenesulfonamideYield 47.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A slurry of 7-bromo-N-(1-methyl-1H-pyrazol-3-yl)-2-quinoxalinamine (0.37 mmol), N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide (0.55 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.03 mmol) in 1,4-dioxane (4 ml) and 2M solution potassium carbonate (2 ml) was stirred at 100° C. for 2 hours. The reaction was cooled to ambient temperature, separated the organic layer and purified directly on silica by column chromatography (10% methanol/ethyl acetate). The desired fractions were combined and concentrated to give the title compound (81 mg, 32%) as a pale green solid. MS(ES)+ m/e 458.1 [M+H]+.

Workup

  1. customseparated the organic layer
  2. custompurified directly on silica by column chromatography (10% methanol/ethyl acetate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1513a8fc916645e39a04f0f2d5de7053
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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