Sodium hydride → 2-(6-Chloropyridazin-3-yl)-1-(2,4-difluorophenyl)ethanone

HRID 1930024노트

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HRID 1930024 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[Cl:12][C:13]1[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=1.[H-].[Na+]>COCCOC>[Cl:12][C:13]1[N:14]=[N:15][C:16]([CH2:10][C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])=[O:11])=[CH:17][CH:18]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydride2회HCID 673313,6-Dichloropyridazine2회HCID 677702,4-Difluoroacetophenone

생성물 1

HCID 579298942-(6-Chloropyridazin-3-yl)-1-(2,4-difluorophenyl)ethanone수율 57%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
50 °C

실험 절차

The 1-(2,4-difluorophenyl)ethanone (Apollo, 1.00 g, 6.40 mmol) and 3,6-dichloropyridazine (0.95 g, 6.4 mmol) in DME (10 mL) were treated with NaH (0.512 g, 12.8 mmol, 60% dispersion in oil) then warmed at about 50° C. in an oil bath. The mixture was stirred for about 4 h then sodium hydride (0.26 g, 6.4 mmol, 60% dispersion in oil) and 3,6-dichloropyridazine (0.48 g, 3.2 mmol) were added. The reaction was heated for about 0.5 h and then quenched with acetic acid and water. The mixture was extracted with EtOAc then purified by flash chromatography on silica with EtOAc as an eluent to give the title compound (0.98 g, 57%): LC/MS (Table 1, Method a) Rt=2.34 min; MS m/z: 269.1 (M+H)+.

후처리

  1. temperatureThe reaction was heated for about 0.5 h
  2. customquenched with acetic acid and water
  3. extractionThe mixture was extracted with EtOAc
  4. customthen purified by flash chromatography on silica with EtOAc as an eluent

출처 및 근거

ORD 기록
ord-ac4047b99f1b40caa62e2db5c0718d05
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188083B2

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