Potassium Carbonate → N-(2-chloro-5-{3-[3-(dimethylamino)-1-piperidinyl]-6-quinoxalinyl}-3-pyridinyl)benzenesulfonamide

HRID 734966Notes

Reaction equation

HRID 734966 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][CH2:15][CH:14]([N:18]([CH3:20])[CH3:19])[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[C:45]1[CH:46]=[C:47]([NH:52][S:53]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)(=[O:55])=[O:54])[C:48]([Cl:51])=[N:49][CH:50]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:51][C:48]1[C:47]([NH:52][S:53]([C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)(=[O:55])=[O:54])=[CH:46][C:45]([C:2]2[CH:11]=[C:10]3[C:5](=[CH:4][CH:3]=2)[N:6]=[CH:7][C:8]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([N:18]([CH3:20])[CH3:19])[CH2:13]2)=[N:9]3)=[CH:50][N:49]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 57843322N-(5-Bromo-2-chloropyridin-3-yl)benzenesulfonamideHCID 685062171-(7-bromo-2-quinoxalinyl)-N,N-dimethyl-3-piperidinamine

Product 1

HCID 57843447N-(2-chloro-5-{3-[3-(dimethylamino)-1-piperidinyl]-6-quinoxalinyl}-3-pyridinyl)benzenesulfonamideYield 10%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A slurry of 1-(7-bromo-2-quinoxalinyl)-N,N-dimethyl-3-piperidinamine (1.2 mmol), bis(pinacolato)diboron (1.30 mmol), potassium acetate (4.80 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.09 mmol) in 1,4-dioxane (5 ml) was heated at 100° C. After the reaction stirred for 2.5 hours, N-(5-bromo-2-chloro-3-pyridinyl)benzenesulfonamide (1.20 mmol) and 2M solution potassium carbonate (5 ml) was added and continued to stir for 18 hours. The reaction was cooled to ambient temperature, concentrated, redissolved in methanol and purified on reverse phase HPLC (0.1% trifluoracetic acid/water in acetonitrile). The desired fractions were combined, neutralized with saturated sodium bicarbonate, extracted with ethyl acetate (3×20 ml). Combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to give the title compound (52 mg, 10%) as a yellow solid. MS(ES)+ m/e 524.2 [M+H]+.

Workup

  1. stirringto stir for 18 hours
  2. concentrationconcentrated
  3. dissolutionredissolved in methanol
  4. custompurified on reverse phase HPLC (0.1% trifluoracetic acid/water in acetonitrile)
  5. extractionextracted with ethyl acetate (3×20 ml)
  6. washCombined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d3c363f1391c49c3bd918d24e9bfda5b
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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