Cesium carbonate → HCID 90010418, compound

HRID 1503297Notes

Reaction equation

HRID 1503297 reaction equation
[Cl:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][NH:4][N:3]=1.Br[C:11]([CH3:18])([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]([C:11]([CH3:18])([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 178526866HCID 178526866, compound

Product 1

HCID 90010418HCID 90010418, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-chloro-4-nitro-1H-pyrazole (1.0 g, 6.8 mmol) in DMF (30 mL) was added ethyl 2-bromo-2-methylpropanoate (2.00 g, 10.2 mmol) and Cs2CO3 (4.40 g, 13.6 mmol). The mixture was stirred at 100° C. for 2 h. After filtration, the solution was poured into water and extracted with ethyl acetate for 3 times. The organic layers were combined and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography to afford the title compound (1.2 g, 68%) as yellowish oil. LC-MS (ESI): m/z=262.0 (M+H)+.

Workup

  1. filtrationAfter filtration
  2. additionthe solution was poured into water
  3. extractionextracted with ethyl acetate for 3 times
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-051ed5bdcdfc438a826c0a77d9d8ff50
Source dataset
uspto-grants-2015_12
Patent number
US09212173B2

Reaction notes

Loading…