Water → 9-{4-[(1-Methyl-1H-benzimidazol-2-yl)oxy]phenyl}-9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridine

HRID 572179Notes

Reaction equation

HRID 572179 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:12]3[C:7](=[N:8][CH:9]=[CH:10][CH:11]=3)[N:6]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[C:5]=12.[H-].[Na+].Cl[C:23]1[N:27]([CH3:28])[C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[N:24]=1.O>CN(C=O)C>[CH3:28][N:27]1[C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[N:24]=[C:23]1[O:19][C:16]1[CH:17]=[CH:18][C:13]([N:6]2[C:7]3=[N:8][CH:9]=[CH:10][CH:11]=[C:12]3[N:4]3[CH:3]=[CH:2][N:1]=[C:5]23)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 6630802-chloro-1-methyl-1H-1,3-benzodiazoleHCID 867049864-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenol

Product 1

HCID 867049889-{4-[(1-Methyl-1H-benzimidazol-2-yl)oxy]phenyl}-9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridineYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-(9H-imidazo[1′,2′:1,2]imidazo[4,5-b]pyridin-9-yl)phenol (150 mg) in DMF (2 mL) was added sodium hydride (60% in oil, 28 mg) at room temperature by small portions. After stirring for 10 min, a solution of 2-chloro-1-methyl-1H-benzimidazole (117 mg) in DMF (1.5 mL) was added, and the obtained mixture was stirred under microwave irradiation at 180° C. for 30 min. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/THF) and recrystallized from methanol to give the title compound (194 mg).

Workup

  1. stirringthe obtained mixture was stirred under microwave irradiation at 180° C. for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (hexane/THF)
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-42b21d18362f4abea4754997fbf913e9
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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