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 587472Notes

Reaction equation

HRID 587472 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-a4d07f3c0cbd4466b699eca749127c81
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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