Methyl iodide → Ethyl 3-(4-chlorophenyl)-1-methyl-1H-pyrazole-5-carboxylate

HRID 915402Notes

Reaction equation

HRID 915402 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[NH:8][N:7]=1)=[O:5])[CH3:2].[CH3:18]I.[OH-].[K+]>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:18])[N:8]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[CH:10]=1)=[O:5])[CH3:2].[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[N:8]([CH3:18])[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178468626HCID 178468626, compound

Product 2

HCID 45790142Ethyl 3-(4-chlorophenyl)-1-methyl-1H-pyrazole-5-carboxylateHCID 45790143ethyl 5-(4-chlorophenyl)-1-methyl-1H-pyrazole-3-carboxylate

Procedure

In analogy to the procedure described for example 2 a], 5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (T. van Herk et al., J. Med. Chem. 2003, 46, 3945-3951) was reacted with methyl iodide in the presence of potassium hydroxide to to give 5-(4-chloro-phenyl)-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester as colorless crystals and 5-(4-chloro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid ethyl ester as colorless oil.

Sources & evidence

ORD record
ord-581b49951e7b4bcc88afe75876bc113f
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

Loading…