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1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 7-methyl-3-{4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 82552
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인쇄 미리보기

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HRID 82552 반응식
CC([O-])(C)C.[Na+].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.Cl[C:50]1[C:55]([NH:56][C:57](=[O:63])OC(C)(C)C)=[C:54]([CH3:64])[CH:53]=[CH:52][N:51]=1.[CH3:65][Si:66]([CH3:89])([CH3:88])[CH2:67][CH2:68][O:69][CH2:70][N:71]1[C:75]2[CH:76]=[CH:77][CH:78]=[CH:79][C:74]=2[N:73]=[C:72]1[O:80][C:81]1[CH:87]=[CH:86][C:84]([NH2:85])=[CH:83][CH:82]=1>C1(C)C=CC=CC=1.CC(O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:64][C:54]1[CH:53]=[CH:52][N:51]=[C:50]2[N:85]([C:84]3[CH:83]=[CH:82][C:81]([O:80][C:72]4[N:71]([CH2:70][O:69][CH2:68][CH2:67][Si:66]([CH3:88])([CH3:89])[CH3:65])[C:75]5[CH:76]=[CH:77][CH:78]=[CH:79][C:74]=5[N:73]=4)=[CH:87][CH:86]=3)[C:57](=[O:63])[NH:56][C:55]=12
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참가 물질

8

반응물 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 585776534-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]anilineHCID 58577713Tert-butyl (2-chloro-4-methylpyridin-3-yl)carbamate

생성물 1

HCID 58577646
7-methyl-3-{4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
수율 37.3%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 3776Isopropanol용매

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온도
100 °C

실험 절차

The mixture of sodium 2-methylpropan-2-olate (0.16 g), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.054 g), tert-butyl (2-chloro-4-methylpyridin-3-yl)carbamate (0.28 g), 4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]aniline (0.41 g) and Pd2(dba)3 (0.043 g) in toluene (40 mL) and 2-propanol (10 mL) was stirred at 100° C. under N2 overnight. After cooling to room temperature, the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-100% EtOAc in hexane) to give 7-methyl-3-{4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (0.21 g) as white crystals.

후처리

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, eluted with 0%-100% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-634062630cff4fcf94e0273dd6631f20
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846713B2

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