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

HRID 734978Notes

Reaction equation

HRID 734978 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-].Br[C:54]1[CH:55]=[C:56]([NH:60][S:61]([CH:64]2[CH2:66][CH2:65]2)(=[O:63])=[O:62])[CH:57]=[N:58][CH:59]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:28][O:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[S:18]([N:15]1[CH2:14][CH2:13][N:12]([C:8]2[CH:7]=[N:6][C:5]3[C:10]([N:9]=2)=[CH:11][C:2]([C:54]2[CH:55]=[C:56]([NH:60][S:61]([CH:64]4[CH2:66][CH2:65]4)(=[O:62])=[O:63])[CH:57]=[N:58][CH:59]=2)=[CH:3][CH:4]=3)[CH2:17][CH2:16]1)(=[O:19])=[O:20]

Participants

8

Reactant 6

HCID 259Bromide ionHCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 57843334N-(5-bromopyridin-3-yl)cyclopropanesulfonamideHCID 685015527-Bromo-2-(4-{[2-(methyloxy)phenyl]sulfonyl}-1-piperazinyl)quinoxaline

Product 1

HCID 57843433N-{5-[3-(4-{[2-(methyloxy)phenyl]sulfonyl}-1-piperazinyl)-6-quinoxalinyl]-3-pyridinyl}cyclopropanesulfonamideYield 14%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A slurry of 7-bromo-2-(4-{[2-(methyloxy)phenyl]sulfonyl}-1-piperazinyl)quinoxaline (0.96 mmol), bis(pinacolato)diboron (0.54 mmol), potassium acetate (1.16 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, a bromide such as N-(5-bromo-3-pyridinyl)cyclopropanesulfonamide (0.54 mmol) and 2M solution potassium carbonate (4 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 (80% ethyl acetate/hexanes). The desired fractions were combined and concentrated to give the title compound (44 mg, 14% yield) as a pale yellow solid. MS(ES)+ m/e 581.3 [M+H]+.

Workup

  1. stirringto stir for 1 hour
  2. customseparated the organic layer
  3. custompurified directly on silica by column chromatography (80% ethyl acetate/hexanes)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-989baa93c690440c913f2bd6d86b4220
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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