Water → 9-(4-{[3-(2-Methoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]oxy}phenyl)-5-methyl-9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridine

HRID 572192Notes

Reaction equation

HRID 572192 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[C:9]3[N:10]([CH:11]=[CH:12][N:13]=3)[C:3]=12.CC(C)([O-])C.[K+].[CH3:27][O:28][CH2:29][CH2:30][N:31]1[C:35]2=[N:36][CH:37]=[CH:38][CH:39]=[C:34]2[N:33]=[C:32]1S(C)(=O)=O.O>CC(N(C)C)=O>[CH3:27][O:28][CH2:29][CH2:30][N:31]1[C:35]2=[N:36][CH:37]=[CH:38][CH:39]=[C:34]2[N:33]=[C:32]1[O:20][C:17]1[CH:18]=[CH:19][C:14]([N:8]2[C:4]3=[N:5][CH:6]=[CH:7][C:2]([CH3:1])=[C:3]3[N:10]3[CH:11]=[CH:12][N:13]=[C:9]23)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 667277733-(2-methoxyethyl)-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 867049944-(5-Methyl-9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenol

Product 1

HCID 867049959-(4-{[3-(2-Methoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]oxy}phenyl)-5-methyl-9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridineYield 86.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

To a solution of 4-(5-methyl-9H-imidazo[1′,2′:1,2]imidazo[4,5-b]pyridin-9-yl)phenol (370 mg) obtained in Example 15, step E) in DMA (3 ml) was added potassium tert-butoxide (168 mg) at room temperature. After stirring for 10 min, a solution of 3-(2-methoxyethyl)-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (383 mg) in DMA (3 ml) was added, and the obtained mixture was stirred at 150° C. for 1 hr. 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 acetone to give the title compound (531 mg).

Workup

  1. stirringthe obtained mixture was stirred at 150° C. for 1 hr
  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 acetone

Sources & evidence

ORD record
ord-3caae54928234c7fa6dc4784b7c98e97
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

Loading…