Cesium carbonate → 2-tert-Butoxycarbonylmethyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl ester

HRID 31530Notes

Reaction equation

HRID 31530 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][N:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 178498471HCID 178498471, compound

Product 1

HCID 586466732-tert-Butoxycarbonylmethyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirring mixture of 5-nitro-2H-pyrazole-3-carboxylic acid methyl ester (3.5 gm, 20.5 mmol) dissolved in 150 ml of acetone was added cesium carbonate (8.01 gm, 24.6 mmol) followed by the addition of tert-butyl bromoacetate (3.61 ml). After 5 hours the solids were filtered and the mixture chromatographed on silica gel using 10% ethyl acetate/hexanes as the eluent to obtain 4.16 gm of pure title product. ESI M+1=286.

Workup

  1. filtrationAfter 5 hours the solids were filtered
  2. customthe mixture chromatographed on silica gel using 10% ethyl acetate/hexanes as the eluent

Sources & evidence

ORD record
ord-b17f059cfb264519bb356a492bd823a3
Source dataset
uspto-grants-2008_09
Patent number
US07425640B2

Reaction notes

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