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

HRID 271080ノート

反応式

HRID 271080 の反応式
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]

参加物

4

反応物 2

HCID 53428795Ethyl 4,6-dichloropyridazine-3-carboxylateHCID 178489560HCID 178489560、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-253eb133e26945d5a80a0781a1b56b86
出典データセット
uspto-grants-2008_11
特許番号
US07452880B2

反応ノート

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