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

HRID 1291293Notes

Reaction equation

HRID 1291293 reaction equation
[CH3:1][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[CH3:13].[H-].[Na+].[F:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1.O>CN(C=O)C>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27][N:12]3[C:5]4[CH:6]=[N:7][N:8]([CH3:11])[C:9](=[O:10])[C:4]=4[C:3]([CH3:13])=[C:2]3[CH3:1])=[CH:25][CH:24]=2)=[O:22])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 47290134-(4-Fluorobenzoyl)benzyl bromideHCID 1356675992,3,5-Trimethyl-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one

Product 1

HCID 699612591-[4-(4-Fluorobenzoyl)benzyl]-2,3,5-trimethyl-1H-pyrrolo [2,3-d]pyridazin-4(5H)-oneYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 2,3,5-trimethyl-1H-pyrrolo[2,3-d]-pyridazin-4(5H)-one (354 mg) in DMF (30 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 1 hour, after which a solution of 4-(4-fluorobenzoyl)benzyl bromide (645 mg) in DMF (15 ml) was added and the mixture was further stirred at room temperature for 2 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 (628 mg, yield 81%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 2 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-11514966b7124f7f9fabb2a694528997
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…