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

HRID 1291287Notes

Reaction equation

HRID 1291287 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][NH:11][C:5]=2[CH:4]=[N:3]1.[H-].[Na+].[Cl:14][C:15]1[CH:30]=[CH:29][C:18]([C:19]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=2)=[O:20])=[CH:17][CH:16]=1.O>CN(C=O)C>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25][N:11]3[C:5]4[CH:4]=[N:3][N:2]([CH3:1])[C:7](=[O:8])[C:6]=4[CH:9]=[CH:10]3)=[CH:23][CH:22]=2)=[O:20])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 1356675915-Methyl-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one

Product 1

HCID 189189201-[4-(4-Chlorobenzoyl)benzyl]-5-methyl-1H-pyrrolo-[2,3-d]pyridazin-4(5H)-oneYield 66.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 5-methyl-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one (298 mg) in DMF (10 ml) was dripped into a suspension of 60% sodium hydride-oil (96 mg) in DMF (8 ml) on an ice-water bath. The mixture was stirred at room temperature for 30 minutes, after which a solution of 4-(4-chlorobenzoyl)benzyl bromide (712 mg) in DMF (15 ml) was added and the mixture was further stirred at room temperature for 1.5 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=1:2) to provide the title compound as white powder (505 mg, yield 57%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 1.5 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=1:2)

Sources & evidence

ORD record
ord-ece5179ad88a43fd88e7fe61cf514292
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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