Cesium carbonate → HCID 82396954, compound

HRID 1777741Notes

Reaction equation

HRID 1777741 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[NH:12]1[CH:16]=[CH:15][N:14]=[N:13]1.C([O-])([O-])=O.[Cs+].[Cs+].O.CC(=O)OCC>CN(C=O)C.[Cu](I)I>[N:12]1[N:13]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][C:9]([OH:11])=[O:10])[N:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27800902-Iodophenylacetic acidHCID 22728543Water ethylacetateHCID 178418936HCID 178418936, compound

Product 1

HCID 82396954HCID 82396954, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-iodophenylacetic acid (500 mg) in DMF (5 mL) was added 1H-1,2,3-triazole (0.214 mL), followed by Cs2CO3 (1.21 g) upon which the temperature increased. The reaction mixture was cooled to RT and copper iodide (17.6 mg) was added. The mixture was stirred at RT overnight and at 110° C. for 1 h30. After cooling down, H2O/EA was added and the phases were separated. The aq. phase was acidified to pH=1 with 1M HCl and extracted with EA. The combined org. phases were dried (Na2SO4) and evaporated in vacuo. The residue was purified by CC (Biotage, SNAP 25 g cartridge, solvent A: Hept; solvent B: EA/AcOH 100/1; gradient in % B: 18 for 4CV, 18 to 100 over 10CV, 100 for 2CV) to afford 235 mg of white solid. LC-MS (B): tR=0.60 min; [M+H]+: 204.42.

Workup

  1. temperatureincreased
  2. temperatureAfter cooling down
  3. customthe phases were separated
  4. extractionextracted with EA
  5. dry with materialphases were dried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by CC (Biotage, SNAP 25 g cartridge, solvent A: Hept; solvent B: EA/AcOH 100/1; gradient in % B: 18 for 4CV, 18 to 100 over 10CV, 100 for 2CV)

Sources & evidence

ORD record
ord-fc315bad20644aa3a688c39ea9a2a67a
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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