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

HRID 1291288노트

반응식

HRID 1291288 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-f001c9558a854b4790dc67f0b110d703
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753664

반응 노트

불러오는 중…