Methyl iodide → HCID 178498598, compound

HRID 1695378Notes

Reaction equation

HRID 1695378 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][N:7]=[C:8]([OH:10])[CH:9]=1)=[O:4].[C:11](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:11])[N:7]=[C:8]([OH:10])[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 1784986025-Hydroxy-1H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 178498598HCID 178498598, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-hydroxy-2H-pyrazole-3-carboxylic acid methyl ester (2.3 g, 16 mmol) in DMF (10 mL) at room temperature was added cesium carbonate (5.27 g, 16 mmol) and methyl iodide (2.3 g, 1.0 mL, 16 mmol) and the resulting mixture stirred for 2.5 h. The mixture was then filtered off to afford the title compound (434 mg, 17%) as a white solid after trituration with ethyl acetate. MS: m/e=157.2 [M+H]+.

Workup

  1. filtrationThe mixture was then filtered off

Sources & evidence

ORD record
ord-f0aea6468f3442e7ab397bb7f3e12d66
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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