Cesium carbonate → HCID 86004373, compound

HRID 1867520Notes

Reaction equation

HRID 1867520 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10]3[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=3)[CH:8]=[CH:9][C:2]=12.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:24][CH2:25][F:26]>CN(C=O)C>[F:26][CH2:25][CH2:24][O:16][C:12]1[CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:2]3[C:3]([CH:6]=2)=[N:4][O:5][N:1]=3)[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 129822-Fluoroethyl bromideHCID 68880821HCID 68880821, compound

Product 1

HCID 86004373HCID 86004373, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

600 mg (2.83 mmol) 3-benzo[1,2,5]oxadiazol-5-yl-phenol are dissolved in 15 mL DMF and stirred for 20 hours at room temperature in the presence of 1.15 g (1.25 eq.) cesium carbonate and 0.264 mL 1-bromo-2-fluoroethane. The reaction mixture is extracted with water and ethyl acetate, the combined organic phases are washed with water and brine, dried with magnesium sulfate and evaporated to dryness. The residue is column chromatographed (gradient from hexane to hexane/ethyl acetate 3:2) to yield the desired product as a pale yellow powder. MS(ES+): 259 (M+1).

Workup

  1. extractionThe reaction mixture is extracted with water and ethyl acetate
  2. washthe combined organic phases are washed with water and brine
  3. dry with materialdried with magnesium sulfate
  4. customevaporated to dryness
  5. customchromatographed (gradient from hexane to hexane/ethyl acetate 3:2)

Sources & evidence

ORD record
ord-705ff33980d84ca6a47fe84539415e06
Source dataset
uspto-grants-2009_12
Patent number
US07632851B2

Reaction notes

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