Benzyl Bromide → 5-benzylpyrrolo[1,2-b]cinnolin-10(5H)-one

HRID 1639253Notes

Reaction equation

HRID 1639253 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[C:13]=1[C:12](=[O:14])[C:11]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(=O)CC>[CH2:21]([N:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[C:12](=[O:14])[C:13]2=[CH:1][CH:2]=[CH:3][N:4]12)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 113213465h-Pyrrolo[1,2-b]cinnolin-10-one

Product 1

HCID 141715785-benzylpyrrolo[1,2-b]cinnolin-10(5H)-oneYield 58.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred slurry containing pyrrolo[1,2-b]cinnolin-10(5H)-one (4.0 g) and potassium carbonate (11.2 g) in 100 ml of 2-butanone was treated with benzyl bromide (4.0 g) and the mixture was stirred at 60°. After 4 h the mixture was quenched with 700 ml of H2O and extracted with two 150 ml portions of dichloromethane. These organic extracts were dried over MgSO4, filtered and concentrated to a green oil. This oil was purified by flash chromatography (silica, dichloromethane) to a yellow solid which was recrystallized from dichloromethane to give 3.5 g of bright yellow crystals, mp 146°-148°.

Workup

  1. customAfter 4 h the mixture was quenched with 700 ml of H2O
  2. extractionextracted with two 150 ml portions of dichloromethane
  3. dry with materialThese organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a green oil
  6. customThis oil was purified by flash chromatography (silica, dichloromethane) to a yellow solid which
  7. customwas recrystallized from dichloromethane

Sources & evidence

ORD record
ord-c7c40baad2aa4c6fb70e242778c69f80
Source dataset
uspto-grants-1989_11
Patent number
US04883794

Reaction notes

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