Water → 1-[3-(4-Chlorobenzoyl)benzyl]-2,3-dichloro-5-methyl-1H-pyrrolo [2,3-d]pyridazin-4(5H)-one

HRID 1291285Notes

Reaction equation

HRID 1291285 reaction equation
[Cl:1][C:2]1[NH:12][C:5]2[CH:6]=[N:7][N:8]([CH3:11])[C:9](=[O:10])[C:4]=2[C:3]=1[Cl:13].[H-].[Na+].[Cl:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([C:23]2[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=2)[CH2:26]Br)=[O:22])=[CH:19][CH:18]=1.O>CN(C=O)C>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([C:23]2[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=2)[CH2:26][N:12]2[C:5]3[CH:6]=[N:7][N:8]([CH3:11])[C:9](=[O:10])[C:4]=3[C:3]([Cl:13])=[C:2]2[Cl:1])=[O:22])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 136496533-(4-Chlorobenzoyl)benzyl bromideHCID 1356675802,3-Dichloro-5-methyl-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one

Product 1

HCID 699619661-[3-(4-Chlorobenzoyl)benzyl]-2,3-dichloro-5-methyl-1H-pyrrolo [2,3-d]pyridazin-4(5H)-oneYield 16.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 2,3-dichloro-5-methyl-1H-pyrrolo [2,3-d]pyridazin-4(5H)-one (303 mg) in DMF (50 ml) was dripped into a suspension of 60% sodium hydride-oil (72 mg) in DMF (10 ml) on an ice-water bath. The mixture was stirred at room temperature for 2.5 hours, after which a solution of 3-(4-chlorobenzoyl) benzyl bromide (511 mg) in DMF (10 ml) was added and the mixture was further stirred at room temperature for 17 hours. The reaction was stopped by adding water and the reaction mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developer; n-hexane: ethyl acetate=1:1) to provide the title compound as white powder (104 mg, yield 16%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 17 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (developer; n-hexane: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-8c17ea975fe84c76b156ac31b81b89ce
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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