Ethyl 4,6-dichloropyridazine-3-carboxylate → (4,6-Dichloro-pyridazin-3-yl)-(2-methoxy-phenyl)-methanone

HRID 271080노트

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HRID 271080 반응식
C(O[C:4]([C:6]1[N:7]=[N:8][C:9]([Cl:13])=[CH:10][C:11]=1[Cl:12])=[O:5])C.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Mg]Br>C1COCC1>[Cl:12][C:11]1[CH:10]=[C:9]([Cl:13])[N:8]=[N:7][C:6]=1[C:4]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][CH3:14])=[O:5]

참가 물질

4

반응물 2

HCID 53428795Ethyl 4,6-dichloropyridazine-3-carboxylateHCID 178489560HCID 178489560, 화합물

생성물 1

HCID 59834303(4,6-Dichloro-pyridazin-3-yl)-(2-methoxy-phenyl)-methanone수율 78.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

4,6-Dichloro-pyridazine-3-carboxylic acid ethyl ester (1.032 g, 4.67 mmol, prepared as described by Xie et al., WO 2004031174) was dissolved in 25 ml dry THF, and the reaction mixture was cooled in a dry ice/acetone bath for 15 minutes. 2-Methoxyphenyl magnesium bromide (7 mL of 1M solution in THF, 7.00 mmol) was added, and the reaction mixture was stirred for 8 hours under nitrogen at −78° C. Silica gel (11.0 g) was added, and the reaction mixture was allowed to warm to room temperature. Solvent was removed under reduced pressure, and the residue was purified by flash chromatography (0% to 20% EtOAc/Hexanes) to yield 1.029 g (3.65 mmol, 78%) of (4,6-dichloro-pyridazin-3-yl)-(2-methoxy-phenyl)-methanone as a yellow solid. Mass Spec. M+H=283.

후처리

  1. temperaturethe reaction mixture was cooled in a dry ice/acetone bath for 15 minutes
  2. additionSilica gel (11.0 g) was added
  3. temperatureto warm to room temperature
  4. customSolvent was removed under reduced pressure
  5. customthe residue was purified by flash chromatography (0% to 20% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-253eb133e26945d5a80a0781a1b56b86
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452880B2

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