Potassium Carbonate → HCID 57486431, compound

HRID 1821688Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[C:12]([CH3:18])=[N:13][N:14]([CH3:17])[C:15]=1[OH:16])=[O:10].[Cl:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[N:22][C:21]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34].C(=O)([O-])[O-].[K+].[K+]>>[Cl:19][C:20]1[CH:25]=[C:24]([O:16][C:15]2[N:14]([CH3:17])[N:13]=[C:12]([CH3:18])[C:11]=2[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[O:10])[N:23]=[N:22][C:21]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34]

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 23013971HCID 23013971, compound

HCID 178434070HCID 178434070, compound

Product 1

HCID 57486431HCID 57486431, compoundYield 80.6%

Conditions

Temperature: 130 °C

Procedure

109 mg (0.382 mmol) of (2,4-dichlorophenyl)(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)methanone, 1.62 g (6.35 mmol) of 4,6-dichloro-3-(2-methylphenoxy)pyridazine obtained in Example 1 (2) and 107 mg (0.775 mmol) of potassium carbonate were mixed, and the mixture was stirred at 130° C. for 14 hours. The reaction mixture was cooled up to room temperature, and purified by silica gel column chromatography (hexane:ethyl acetate, gradient) to obtain 155 mg (0.308 mmol, Yield: 80.6%) of (5-{[5-chloro-6-(2-methylphenoxy)-3-pyridazinyl]oxy}-1,3-dimethyl-1H-pyrazol-4-yl)(2,4-dichlorophenyl)methanone.

Workup

temperatureThe reaction mixture was cooled up to room temperature
custompurified by silica gel column chromatography (hexane:ethyl acetate, gradient)

Sources & evidence

ORD record: ord-d52bc6380a8941b29e81499a895b46fd
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608563B2

Reaction notes

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