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

HRID 572191Notes

Reaction equation

HRID 572191 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][N:28]1[C:32]2=[N:33][CH:34]=[CH:35][CH:36]=[C:31]2[N:30]=[C:29]1S(C)(=O)=O.O>CC(N(C)C)=O>[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]([O:20][C:29]4[N:28]([CH3:27])[C:32]5=[N:33][CH:34]=[CH:35][CH:36]=[C:31]5[N:30]=4)=[CH:16][CH:15]=3)[C:9]3[N:10]([CH:11]=[CH:12][N:13]=3)[C:3]=12

Participants

6

Reactant 4

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 585773713-Methyl-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 665579805-Methyl-9-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridineYield 64.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-(5-methyl-9H-imidazo[1′,2′:1,2]imidazo[4,5-b]pyridin-9-yl)phenol (238 mg) in DMA (4 ml) was added potassium tert-butoxide (112 mg) at room temperature. After stirring for 10 min, 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (211 mg) 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 (THF) and recrystallized from hexane/THF to give the title compound (229 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 (THF)
  7. customrecrystallized from hexane/THF

Sources & evidence

ORD record
ord-9112c891e8ed48ba8b4c103dbdea86ef
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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