Potassium Carbonate → HCID 18408531, compound

HRID 993021Notes

Reaction equation

CO[CH2:3][N:4]1[C:8]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)=[CH:7][C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:5]1.C(=O)([O-])[O-].[K+].[K+].Cl.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35](CCl)[CH:34]=1>CN(C=O)C>[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:3][N:4]2[C:8]([C:9]3[CH:10]=[C:11]([O:19][CH3:20])[C:12]([O:17][CH3:18])=[C:13]([O:15][CH3:16])[CH:14]=3)=[CH:7][C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:5]2)[CH:34]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl 1-methoxymethyl-5-(3,4,5-trimethoxyphenyl)-pyrazole-3-carboxylate (820 mg) was dissolved in DMF (4 mL), and to the solution potassium carbonate (325 mg) and 3-picolyl chloride hydrochloride (193 mg) were added, and the mixture was stirred at 50° C. for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed with water and saturated brine and dried over anhydrous sodium sulfate. After concentrating the diluted residue, the resultant residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2 to 0:1) to obtain the title compound.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additionthe residue was diluted with ethyl acetate
washwashed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationAfter concentrating the diluted residue
customthe resultant residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2 to 0:1)

Sources & evidence

ORD record: ord-9e9baf4e4ca04ddbb7923f0476cabe60
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472386B1

Reaction notes

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