Cesium carbonate → 2-fluoro-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzonitrile

HRID 1877453

반응식

HRID 1877453 반응식
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:59][O:60][C:61]1[CH:62]=[C:63]([C:67]2[C:79]3[C:78]4[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=4)[NH:72][C:71]=3[CH:70]=[CH:69][CH:68]=2)[CH:64]=[N:65][CH:66]=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:10][C:4]1[CH:3]=[C:2]([N:72]2[C:71]3[CH:70]=[CH:69][CH:68]=[C:67]([C:63]4[CH:64]=[N:65][CH:66]=[C:61]([O:60][CH3:59])[CH:62]=4)[C:79]=3[C:78]3[C:73]2=[CH:74][CH:75]=[CH:76][CH:77]=3)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7360294-Bromo-2-fluorobenzonitrileHCID 673084644-(5-methoxypyridin-3-yl)-9H-carbazole

생성물 1

HCID 673080012-fluoro-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzonitrile수율 80%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

실험 절차

0.74 g of 4-bromo-2-fluorobenzonitrile, 3.07 g of caesium carbonate, 0.172 g of (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) and 0.055 g of palladium acetate are successively added, under argon, to a solution of 0.68 g of 4-(5-methoxypyridin-3-yl)-9H-carbazole in 30 ml of dioxane. The reaction mixture is refluxed for 2 and a half hours, cooled to ambient temperature, filtered through celite and concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a mixture of cyclohexane and ethyl acetate (80/20 by volume), so as to give 0.78 g of 2-fluoro-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzonitrile in the form of a colourless oil, the characteristics of which are the following:

후처리

  1. temperatureThe reaction mixture is refluxed for 2 and a half hours
  2. filtrationfiltered through celite and
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by silica gel chromatography, elution
  5. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (80/20 by volume)

출처 및 근거

ORD 기록
ord-2320c06f8ea74d21bed34d755ae094c0
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309721B2

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