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

HRID 1291288ノート

反応式

HRID 1291288 の反応式
[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+].[F: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>[F: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

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 47290134-(4-Fluorobenzoyl)benzyl bromideHCID 1356675915-Methyl-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one

生成物 1

HCID 189192541-[4-(4-Fluorobenzoyl)benzyl]-5-methyl-1H-pyrrolo-[2,3-d]pyridazin-4(5H)-one収率 68.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

A solution of 5-methyl-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one (373 mg) in DMF (10 ml) was dripped into a suspension of 60% sodium hydride-oil (120 mg) in DMF (10 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 (806 mg) in DMF (20 ml) was added and the mixture was further stirred at room temperature for 13 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; dichloromethane: methanol=99:1) to provide the title compound as white powder (615 mg, yield 68%).

後処理

  1. stirringthe mixture was further stirred at room temperature for 13 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; dichloromethane: methanol=99:1)

出典と根拠

ORDレコード
ord-f001c9558a854b4790dc67f0b110d703
出典データセット
uspto-grants-1998_05
特許番号
US05753664

反応ノート

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