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 82552Notes

Reaction equation

HRID 82552 reaction equation
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

Participants

8

Reactant 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

Product 1

HCID 585776467-methyl-3-{4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneYield 37.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-634062630cff4fcf94e0273dd6631f20
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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