Cesium carbonate → HCID 86702817, compound

HRID 1850056Notes

Reaction equation

HRID 1850056 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH:17]1[CH:21]=[C:20](/[CH:22]=[CH:23]/[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:19]=[N:18]1>C(#N)C>[O:10]([CH2:9][CH2:8][N:17]1[CH:21]=[C:20](/[CH:22]=[CH:23]/[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:19]=[N:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 86702818HCID 86702818, compound

Product 1

HCID 86702817HCID 86702817, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Cesium carbonate (0.490 g, 1.5 mmol) and 1-(2-bromoethoxy)benzene (0.261 g, 1.30 mmol) were 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 overnight at 80° C. The reaction mixture was then cooled down to room temperature and the precipitated solids were filtered off. The filtrate was concentrated and purified by silica gel column chromatography using a gradient of 0-60% of EtOAc in hexanes to provide the title compound (0.203 g, 71%) as a colorless oil. ES+(M+H)+287

Workup

  1. temperatureThe reaction mixture was then cooled 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-70bb5f83e60b404ebc5b4213e353e1bf
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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