Potassium Carbonate → HCID 57843438, compound

HRID 734980Notes

Reaction equation

HRID 734980 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]([S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH2:14][CH2:13]3)=[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>[CH3:22][N:21]([CH3:23])[S:18]([CH:15]1[CH2:16][CH2:17][N:12]([C:8]2[CH:7]=[N:6][C:5]3[C:10](=[CH:11][C:2]([C:32]4[CH:37]=[N:36][CH:35]=[C:34]([NH:38][S:39]([C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=5)(=[O:41])=[O:40])[CH:33]=4)=[CH:3][CH:4]=3)[N:9]=2)[CH2:13][CH2:14]1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 52936632N-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]benzenesulfonamideHCID 68508222HCID 68508222, compound

Product 1

HCID 57843438HCID 57843438, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A slurry of 1-(7-bromo-2-quinoxalinyl)-N,N-dimethyl-4-piperidinesulfonamide (0.43 mmol), N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide (0.47 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 18 hours. The reaction was cooled to ambient temperature, separated the organic layer and purified directly on silica by column chromatography (5% methanol/ethyl acetate). The desired fractions were combined and concentrated to give the title compound (102 mg, 43% yield) as a yellow solid. MS(ES)+ m/e 539.2 [M+H]+.

Workup

  1. customseparated the organic layer
  2. custompurified directly on silica by column chromatography (5% methanol/ethyl acetate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bac322d1f6a84243bb83dd7e4eaff730
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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