Cesium carbonate → HCID 68878067, compound

HRID 1867519Notes

Reaction equation

HRID 1867519 reaction equation
[Br:1][CH2:2][CH2:3]F.[C:5]([O:9][C:10](=[O:30])[N:11]([C:13]1[CH:18]=CC(C2C=CC3C(C=2)=NON=3)=[C:15]([O:28][CH3:29])[CH:14]=1)[CH3:12])([CH3:8])([CH3:7])[CH3:6].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:5]([O:9][C:10](=[O:30])[N:11]([C:13]1[CH:18]=[CH:3][C:2]([Br:1])=[C:15]([O:28][CH3:29])[CH:14]=1)[CH3:12])([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 129822-Fluoroethyl bromideHCID 68877688HCID 68877688, compound

Product 1

HCID 68878067HCID 68878067, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
52.5 °C

Procedure

0.63 mL (1.25 eq.) 1-bromo-2-fluoroethane are added at room temperature to a stirred suspension of 2 g (6.6 mmol) (4-benzo[1,2,5]oxadiazol-5-yl-3-methoxy-phenyl)-methyl-carbamic acid tert-butyl ester and 3.2 g (1.5 eq.) cesium carbonate in 50 mL DMF. After stirring for 12 hours at 50 to 55° C., the reaction mixture is cooled to rt. And extracted with water/ethyl acetate. The combined organic phases are washed with brine, dried over magnesium sulfate and evaporated to yield the desired product as a yellow oil, which is used without further purification.

Workup

  1. temperaturethe reaction mixture is cooled to rt
  2. extractionAnd extracted with water/ethyl acetate
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-6fcf836f134d4494a1c9988a71378ffb
Source dataset
uspto-grants-2009_12
Patent number
US07632851B2

Reaction notes

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