Cesium carbonate → HCID 86702820, compound

HRID 1850061Notes

Reaction equation

HRID 1850061 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[CH:11]=[C:10](/[CH:12]=[CH:13]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[N:8]1.Br[CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C>[CH2:20]([N:7]1[CH:11]=[C:10](/[CH:12]=[CH:13]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[N:8]1)[CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 5357478Cinnamyl bromideHCID 86702818HCID 86702818, compound

Product 1

HCID 86702820HCID 86702820, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

Cesium carbonate (0.490 g, 1.5 mmol) was added to a solution of (E)-ethyl 3-(1H-pyrazol-4-yl)acrylate (0.167 g, 1 mmol) in ACN (8 mL) at room temperature. The suspension was stirred and 1-((E)-3-bromoprop-1-enyl)benzene (0.256 g, 1.30 mmol) was added. The mixture was heated at 40° C. overnight. After cooling down to room temperature, the precipitated solids were filtered off. The filtrate was concentrated and purified by silica gel column chromatography using a 0-60% gradient of EtOAc in hexanes to provide the title compound as a colorless oil (0.214 g, 76%). ES+(M+H)+283

Workup

  1. temperatureAfter cooling down to room temperature
  2. filtrationthe precipitated solids were filtered off
  3. concentrationThe filtrate was concentrated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-d5c921940b5a4c66b37a185d2d876297
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

Loading…