Sodium Bicarbonate → N,N-dimethyl-N'-{5-[3-(1-methyl-1H-pyrazol-4-yl)-6-quinoxalinyl]-3-pyridinyl}sulfamide

HRID 734962Notes

Reaction equation

HRID 734962 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([C:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=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[C:42]1[CH:43]=[C:44]([NH:48][S:49]([N:52]([CH3:54])[CH3:53])(=[O:51])=[O:50])[CH:45]=[N:46][CH:47]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.O.ClCCl.CCOCC>[CH3:53][N:52]([CH3:54])[S:49]([NH:48][C:44]1[CH:45]=[N:46][CH:47]=[C:42]([C:2]2[CH:11]=[C:10]3[C:5](=[CH:4][CH:3]=2)[N:6]=[CH:7][C:8]([C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)=[N:9]3)[CH:43]=1)(=[O:50])=[O:51]

Participants

10

Reactant 5

HCID 516892Sodium BicarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 578432587-bromo-2-(1-methyl-1H-pyrazol-4-yl)quinoxalineHCID 57843357N'-(5-bromo-3-pyridinyl)-N,N-dimethylsulfamide

Product 1

HCID 57843459N,N-dimethyl-N'-{5-[3-(1-methyl-1H-pyrazol-4-yl)-6-quinoxalinyl]-3-pyridinyl}sulfamideYield 57%

Reagents, catalysts & solvents 4

HCID 6344DichloromethaneCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

In an oven dried high pressure vessel under a nitrogen atmosphere, 7-bromo-2-(1-methyl-1H-pyrazol-4-yl)quinoxaline (150 mg, 0.519 mmol), bis(pinacolato)diboron (158 mg, 0.623 mmol), potassium acetate (153 mg, 1.556 mmol), and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (18.98 mg, 0.026 mmol) in anhydrous 1,4-dioxane (2 mL) was stirred at 100° C. in an oil bath for 1 hr. The reaction mixture was cooled to room temperature. N′-(5-bromo-3-pyridinyl)-N,N-dimethylsulfamide (145 mg, 0.519 mmol) followed by sodium bicarbonate (131 mg, 1.556 mmol) in water (0.67 mL) were added to the reaction mixture and the vessel was sealed again. The reaction was stirred at 100° C. for 16.75 hours then cooled to room temperature. The reaction was filtered through Celite and the pad was washed with ethyl acetate. The bi-phasic mixture was separated in a separatory funnel. The organic layer was washed with brine (20 mL), dried over magnesium sulfate, and concentrated in vacuo to give a brown solid. Trituration of the brown solid in dichloromethane (3 drops) and ether (8 mL) provided the title compound (120 mg, 57%) as a light brown solid. MS(ES)+ m/e 410.2 [M+H]+.

Workup

  1. customIn an oven dried high pressure vessel under a nitrogen atmosphere
  2. additionwere added to the reaction mixture
  3. customthe vessel was sealed again
  4. temperaturethen cooled to room temperature
  5. filtrationThe reaction was filtered through Celite
  6. washthe pad was washed with ethyl acetate
  7. customThe bi-phasic mixture was separated in a separatory funnel
  8. washThe organic layer was washed with brine (20 mL)
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customto give a brown solid

Sources & evidence

ORD record
ord-4bffdfd25a4b4573a17a28f3443ddd11
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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