Potassium Carbonate → N-{5-[3-(4-{[2-(methylsulfonyl)ethyl]amino}-1-piperidinyl)-6-quinoxalinyl]-3-pyridinyl}benzenesulfonamide

HRID 734971Notes

Reaction equation

HRID 734971 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][CH:15]([NH:18][CH2:19][CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:14][CH2:13]3)=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:33]2[CH:34]=[C:35]([NH:39][S:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)(=[O:42])=[O:41])[CH:36]=[N:37][CH:38]=2)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:24][S:21]([CH2:20][CH2:19][NH:18][CH:15]1[CH2:16][CH2:17][N:12]([C:8]2[CH:7]=[N:6][C:5]3[C:10]([N:9]=2)=[CH:11][C:2]([C:33]2[CH:34]=[C:35]([NH:39][S:40]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)(=[O:41])=[O:42])[CH:36]=[N:37][CH:38]=2)=[CH:3][CH:4]=3)[CH2:13][CH2:14]1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 52936632N-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]benzenesulfonamideHCID 685041941-(7-bromo-2-quinoxalinyl)-N-[2-(methylsulfonyl)ethyl]-4-piperidinamine

Product 1

HCID 57843482N-{5-[3-(4-{[2-(methylsulfonyl)ethyl]amino}-1-piperidinyl)-6-quinoxalinyl]-3-pyridinyl}benzenesulfonamideYield 6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A slurry of a 1-(7-bromo-2-quinoxalinyl)-N-[2-(methylsulfonyl)ethyl]-4-piperidinamine (0.48 mmol), N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide (0.53 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 3 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 (15 mg, 6%) as a tan solid. MS(ES)+ m/e 567.4 [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-95c40a9da7b74770a47f1420b3a55f60
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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