Potassium Carbonate → [1-(4-Bromobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester

HRID 1631917Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[C:6]([CH3:11])=[N:7][NH:8][C:9]=1[CH3:10].[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[C:9]([CH3:10])=[N:8][N:7]([CH2:18][C:17]2[CH:20]=[CH:21][C:14]([Br:13])=[CH:15][CH:16]=2)[C:6]=1[CH3:11]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (3,5-dimethyl-1H-pyrazol-4-yl)-acetic acid methyl ester (6 g, 36 mmol) and 4-bromobenzyl bromide (8.9 g, 36 mmol) in 80 ml acetonitrile was added K2CO3 (4.9 g, 36 mmol). The mixture was stirred for 12 h at room temperature, 12 h at 50° C., and after addition of an additional 1 g of K2CO3 the mixture was stirred for another 12 h at room temperature. The mixture was concentrated by under reduced pressure, poured into water and extracted twice with ethyl acetate, dried with MgSO4 and evaporated under reduced pressure.

Workup

stirringwas stirred for another 12 h at room temperature
concentrationThe mixture was concentrated by under reduced pressure
additionpoured into water
extractionextracted twice with ethyl acetate
dry with materialdried with MgSO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-829b0577e0c24b149d758c295d4f9c21
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791272B2

Reaction notes

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