4-(Bromomethyl)benzophenone → HCID 11326145, compound

HRID 1890624Notes

Reaction equation

HRID 1890624 reaction equation
Br[CH2:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[CH2:17]([C:19]1[NH:20][C:21]2[C:22]([N:29]=1)=[N:23][C:24]([CH3:28])=[CH:25][C:26]=2[CH3:27])[CH3:18].O.[OH-].[Li+]>CN(C=O)C>[CH2:17]([C:19]1[N:29]([CH2:2][C:3]2[CH:16]=[CH:15][C:6]([C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:8])=[CH:5][CH:4]=2)[C:22]2=[N:23][C:24]([CH3:28])=[CH:25][C:26]([CH3:27])=[C:21]2[N:20]=1)[CH3:18]

Participants

5

Reactant 3

HCID 1229514-(Bromomethyl)benzophenoneHCID 168937Lithium hydroxide, monohydrateHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurine

Product 1

HCID 11326145HCID 11326145, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Commercially available 4-bromomethylbenzophenone (5.00 g, 18.2 mmol) was dissolved in DMF (100 mL), and 2-ethyl-5,7-dimethylimidazo[4,5-b]pyridine (3.82 g, 21.8 mmol) and lithium hydroxide monohydrate (0.920 g, 21.9 mmol) was added to the solution, followed by stirring at room temperature for 3 hours. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1), and recrystallized from ethanol to obtain Compound 1 (5.33 g, yield 79%).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f1e0c04690434e9f8aff6fdc553f9469
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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