Potassium Carbonate → 1,1-Dimethylethyl [2-(4-{7-[5-(aminosulfonyl)-3-pyridinyl]-2-quinoxalinyl}-1-piperazinyl)ethyl]carbamate

HRID 734965Notes

Reaction equation

HRID 734965 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]([CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[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[C:52]1[CH:53]=[C:54]([S:58]([NH2:61])(=[O:60])=[O:59])[CH:55]=[N:56][CH:57]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[NH2:61][S:58]([C:54]1[CH:53]=[C:52]([C:2]2[CH:11]=[C:10]3[C:5]([N:6]=[CH:7][C:8]([N:12]4[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:16][CH2:17]4)=[N:9]3)=[CH:4][CH:3]=2)[CH:57]=[N:56][CH:55]=1)(=[O:60])=[O:59]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 126842585-Bromopyridine-3-sulfonamideHCID 866250001,1-Dimethylethyl {2-[4-(7-bromo-2-quinoxalinyl)-1-piperazinyl]ethyl}carbamate

Product 1

HCID 251176481,1-Dimethylethyl [2-(4-{7-[5-(aminosulfonyl)-3-pyridinyl]-2-quinoxalinyl}-1-piperazinyl)ethyl]carbamateYield 7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A slurry of 1,1-dimethylethyl {2-[4-(7-bromo-2-quinoxalinyl)-1-piperazinyl]ethyl}carbamate (0.96 mmol), bis(pinacolato)diboron (1.06 mmol), potassium acetate (3.84 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.07 mmol) in 1,4-dioxane (5 ml) was heated at 100° C. After the reaction stirred for 1 hour, 5-bromo-3-pyridinesulfonamide (0.96 mmol) and 2M potassium carbonate (aq) (4 ml) was added and the reaction mixture stirred for 18 hours. The reaction was cooled to ambient temperature, separated the organic layer and purified directly on silica by column chromatography (10% ethyl acetate/hexanes). The desired fractions were combined and concentrated to give the title compound (20 mg, 7%) as a light yellow solid. MS(ES)+ m/e 514.2 [M+H]+.

Workup

  1. stirringthe reaction mixture stirred for 18 hours
  2. customseparated the organic layer
  3. custompurified directly on silica by column chromatography (10% ethyl acetate/hexanes)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3f40500c914b400383bed8882d958cc9
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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