N-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]benzenesulfonamide → N-[5-(3-{4-[2-(methyloxy)phenyl]-1-piperazinyl}-6-quinoxalinyl)-3-pyridinyl]benzenesulfonamide

HRID 734969Notes

Reaction equation

HRID 734969 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:12]=[N:13][CH:14]=2)O1.Br[C:27]1[CH:36]=[C:35]2[C:30]([N:31]=[CH:32][C:33]([N:37]3[CH2:42][CH2:41][N:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=4[O:49][CH3:50])[CH2:39][CH2:38]3)=[N:34]2)=[CH:29][CH:28]=1>O1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>[CH3:50][O:49][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=1[N:40]1[CH2:39][CH2:38][N:37]([C:33]2[CH:32]=[N:31][C:30]3[C:35]([N:34]=2)=[CH:36][C:27]([C:9]2[CH:10]=[C:11]([NH:15][S:16]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)(=[O:17])=[O:18])[CH:12]=[N:13][CH:14]=2)=[CH:28][CH:29]=3)[CH2:42][CH2:41]1

Participants

5

Reactant 2

HCID 52936632N-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]benzenesulfonamideHCID 685086137-Bromo-2-{4-[2-(methyloxy)phenyl]-1-piperazinyl}quinoxaline

Product 1

HCID 57843306N-[5-(3-{4-[2-(methyloxy)phenyl]-1-piperazinyl}-6-quinoxalinyl)-3-pyridinyl]benzenesulfonamideYield 48.4%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

A slurry of a boronate ester such as N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide (0.55 mmol), 7-bromo-2-{4-[2-(methyloxy)phenyl]-1-piperazinyl}quinoxaline (0.37 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.03 mmol) in 1,4-dioxane (4 ml) and 2M potassium carbonate (aq) (2 ml) was stirred at 100° C. for 18 hours. The reaction was cooled to ambient temperature, the organic layer separated and purified directly on silica by column chromatography (80% ethyl acetate/hexanes). The desired fractions were combined and concentrated to give the title compound (99 mg, 48%) as a yellow solid. MS(ES)+ m/e 553.4 [M+H]+.

Workup

  1. customthe organic layer separated
  2. custompurified directly on silica by column chromatography (80% ethyl acetate/hexanes)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0c90a2e144414cfcb7e3d5d91abb2180
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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