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

HRID 230151Notes

Reaction equation

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]

Participants

Conditions

Temperature: -78 °C

Procedure

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 1 M 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.

Workup

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)

Sources & evidence

ORD record: ord-d5ced89c33dd458b997efd50aa2fe0b8
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566708B2

Reaction notes

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