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

HRID 734965노트

반응식

HRID 734965 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-3f40500c914b400383bed8882d958cc9
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592342B2

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