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

HRID 271080

Reaktionsgleichung

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]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-253eb133e26945d5a80a0781a1b56b86
Quelldatensatz: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07452880B2

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