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

HRID 1625966
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HRID 1625966 반응식
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
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참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

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

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온도
100 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-40e3b2a07cbb4be9a21535c07f82bdaf
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785433B2

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