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2-(Tributylstannyl)furan → 4-(tert-butyl)-N-[3-(2-{[5-(2-furyl)-2-pyrimidinyl]oxy}ethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

HRID 1062719
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인쇄 미리보기

반응식

HRID 1062719 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][CH2:10][O:11][C:12]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[C:15]([NH:24][S:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[N:14]([CH3:38])[N:13]=2)=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:44]1[O:45][CH:46]=[CH:47][CH:48]=1)CCC>O1CCOCC1.C(OCC)(=O)C.C(#N)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:34]([C:31]1[CH:32]=[CH:33][C:28]([S:25]([NH:24][C:15]2[N:14]([CH3:38])[N:13]=[C:12]([O:11][CH2:10][CH2:9][O:8][C:5]3[N:4]=[CH:3][C:2]([C:44]4[O:45][CH:46]=[CH:47][CH:48]=4)=[CH:7][N:6]=3)[C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:27])=[O:26])=[CH:29][CH:30]=1)([CH3:37])([CH3:36])[CH3:35]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 2

HCID 43936882-(Tributylstannyl)furanHCID 9894949N-[3-{2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide

생성물 1

HCID 222820504-(tert-butyl)-N-[3-(2-{[5-(2-furyl)-2-pyrimidinyl]oxy}ethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide수율 86.7%

시약·촉매·용매 4

HCID 6102075
Dichlorobis(triphenylphosphine)palladium
촉매
HCID 6342Acetonitrile용매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

실험 절차

To N-[3-{2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide (Example 3) (277 mg) in 1,4-dioxane (7.5 ml) at room temperature was added 2-(tributylstannyl)furan (329 mg) and bis(triphenylphosphine)palladium (II) chloride (32 mg) the mixture was stirred and heated to reflux for 16 hrs. The reaction was diluted with ethyl acetate.(100 ml) and washed with a 10% solution of potassium fluoride in water (100 ml), the aqueous portion was then extracted with ethyl acetate (100 ml). The organic fractions were separated and combined, washed with brine (100 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica (10 g) eluted with ethyl acetate:hexane (3:2) to yield an oil which was dissolved in acetonitrile (20 ml) and washed with hexane (6×10 ml). Evaporation of the acetonitrile under reduced pressure yielded the title compound as a white solid (235 mg).

후처리

  1. temperatureheated
  2. temperatureto reflux for 16 hrs
  3. wash(100 ml) and washed with a 10% solution of potassium fluoride in water (100 ml)
  4. extractionthe aqueous portion was then extracted with ethyl acetate (100 ml)
  5. customThe organic fractions were separated
  6. washwashed with brine (100 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography on silica (10 g)
  11. washeluted with ethyl acetate:hexane (3:2)
  12. customto yield an oil which
  13. washwashed with hexane (6×10 ml)
  14. customEvaporation of the acetonitrile under reduced pressure

출처 및 근거

ORD 기록
ord-7d92f654fa9049aaa8c46c9032897fc2
출처 데이터셋
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06962923B2

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