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

HRID 734965ノート

反応式

HRID 734965 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-3f40500c914b400383bed8882d958cc9
出典データセット
uspto-grants-2009_09
特許番号
US07592342B2

反応ノート

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