Potassium Carbonate → 3-[(7-{5-[(Phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)amino]benzoic acid

HRID 734974Notes

Reaction equation

HRID 734974 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:14]=[C:15]([CH:19]=[C:20](OC)[CH:21]=3)[C:16]([OH:18])=[O:17])=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:32]2[CH:33]=[C:34]([NH:38][S:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)(=[O:41])=[O:40])[CH:35]=[N:36][CH:37]=2)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:42]1([S:39]([NH:38][C:34]2[CH:33]=[C:32]([C:2]3[CH:11]=[C:10]4[C:5]([N:6]=[CH:7][C:8]([NH:12][C:13]5[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=5)[C:16]([OH:18])=[O:17])=[N:9]4)=[CH:4][CH:3]=3)[CH:37]=[N:36][CH:35]=2)(=[O:41])=[O:40])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 52936632N-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]benzenesulfonamideHCID 685081353-[(7-Bromo-2-quinoxalinyl)amino]-5-(methyloxy)benzoic acid

Product 1

HCID 578434283-[(7-{5-[(Phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)amino]benzoic acidYield 16.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A slurry of 3-[(7-bromo-2-quinoxalinyl)amino]-5-(methyloxy)benzoic acid (0.73 mmol), N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide (0.80 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.06 mmol) in 1,4-dioxane (4 ml) and 2M solution potassium carbonate (2 ml) was stirred at 100° C. for 18 hours. The reaction was cooled to ambient temperature, separated the organic layer and purified directly on silica by column chromatography (100% ethyl acetate). The desired fractions were combined and concentrated to give the title compound (60 mg, 16%) as a yellow solid. MS(ES)+ m/e 497.8 [M+H]+.

Workup

  1. customseparated the organic layer
  2. custompurified directly on silica by column chromatography (100% ethyl acetate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-57fac613d192465581e303ac1a12a843
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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