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Dichloromethane → 3-(4-Morpholinylsulfonyl)-5-[4-(4-pyridinyl)-6-quinolinyl]-2-pyridinamine

HRID 472084
ノート
印刷プレビュー

反応式

HRID 472084 の反応式
Br[C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])[C:5]([NH2:8])=[N:6][CH:7]=1.[N:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31](B4OC(C)(C)C(C)(C)O4)[CH:32]=3)[N:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1.ClCCl.C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[N:12]1([S:9]([C:4]2[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:31]3[CH:32]=[C:33]4[C:28](=[CH:29][CH:30]=3)[N:27]=[CH:26][CH:25]=[C:24]4[C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)[CH:3]=2)(=[O:11])=[O:10])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 621482705-Bromo-3-(morpholinosulfonyl)pyridin-2-amineHCID 667823744-(4-Pyridinyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

生成物 1

HCID 251212683-(4-Morpholinylsulfonyl)-5-[4-(4-pyridinyl)-6-quinolinyl]-2-pyridinamine収率 37%

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 5-bromo-3-(4-morpholinylsulfonyl)-2-pyridinamine (0.296 g, 0.92 mmol), 4-(4-pyridinyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (0.306 mg, 0.92 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II)-complex with dichloromethane(1:1) (37.6 mg, 0.046 mmol), 2 M aqueous K2CO3 (5 mL) and dioxane (5 mL) was heated at 100° C. for 18 h. After cooling to room temperature, the organic layer was separated and the aqueous portion extracted three times with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified twice by silica gel chromatography (eluent: i) 1-5% MeOH in CH2Cl2 and ii) 0-20% MeOH in CH2Cl2) to provide the title compound as a white solid (150 mg, 37% yield). MS (ES)+ m/e 448.0 [M+H]+.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe organic layer was separated
  3. extractionthe aqueous portion extracted three times with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified twice by silica gel chromatography (eluent: i) 1-5% MeOH in CH2Cl2 and ii) 0-20% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-616071253bf64237b2273d571c6c8187
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08633187B2

反応ノート

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