Potassium Iodide → 1-[5-Chloro-2-(4-methoxy-benzyloxy)-benzyl]-5-methyl-1h-pyrazole-3-carboxylic acid ethyl ester

HRID 1527952Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[OH:20])[N:7]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Cl)=[CH:33][CH:32]=1>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:35][C:34]2[CH:37]=[CH:38][C:31]([O:30][CH3:29])=[CH:32][CH:33]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-(5-chloro-2-hydroxy-benzyl)-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester 2 0.2 g (0.6 mmol) in DMF (5 mL) were added potassium carbonate (0.23 g, 1.7 mmol), potassium iodide (0.1 g, 0.6 mmol) and 4-methoxybenzyl chloride (0.1 ml, 0.7 mmol). The resulting mixture was heated at 100° C. in an Emrys microwave reactor for 30 minutes. The volatiles were removed in vacuo. The crude product was purified on silica to yield 1-[5-chloro-2-(4-methoxy-benzyloxy)-benzyl]-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester 13 as a white solid.

Workup

customThe volatiles were removed in vacuo
customThe crude product was purified on silica

Sources & evidence

ORD record: ord-3c0ca17ca0ae418ba6993eee6ac03909
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090566B2

Reaction notes

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