Sodium Iodide → HCID 58760742, compound

HRID 857359Notes

Reaction equation

HRID 857359 reaction equation
[Br:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:15](=O)[CH2:14][CH2:13][N:6]3[C:7]=2[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].[NH4+].[Cl-].C[Si](Cl)(C)C.[Na+].[I-].C([O-])(O)=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>C1COCC1.CC#N.CCOC(C)=O>[CH3:22][O:21][C:19](=[O:20])[CH2:18][CH:15]1[C:5]2=[CH:4][C:3]3[C:2]([Br:1])=[CH:10][C:9]([O:11][CH3:12])=[CH:8][C:7]=3[N:6]2[CH2:13][CH2:14]1

Participants

11

Reactant 7

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 24437Sodium SulfiteHCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 516892Sodium BicarbonateHCID 21867438HCID 21867438, compound

Product 1

HCID 58760742HCID 58760742, compoundYield 82.7%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the ketone from Step 4 (0.4 g, 1.43 mmol), methyl bromoacetate (0.7 mL, 7.1 mmol), and Zn/Cu couple (0.46 g, 7.1 mmol) in THF (6 mL) was suspended in an ultrasound bath for 45 minutes. Saturated NH4Cl solution and EtOAc were then added, and the suspension was filtered through abed of Celite. The organic phase was washed with H2O and brine, dried (MgSO4), filtered and evaporated. The crude material was purified by flash chromatography (1:1 EtOAc/hexane) and the resulting intermediate was dissolved in CH3CN (10 mL). This solution was then added to a stirring mixture of TMSCl (0.8 mL, 6.4 mmol) and NaI (0.95 g, 6.4 mmol) in CH3CN (4 mL) in a RT H2O bath. Saturated NaHCO3 solution and sodium sulfite were added, and the product was extracted with EtOAc. The organic layer was washed with H2O and brine, dried (MgSO4), filtered, and evaporated to give a pale yellow solid (0.40 g).

Workup

  1. filtrationthe suspension was filtered through abed of Celite
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude material was purified by flash chromatography (1:1 EtOAc/hexane)
  7. dissolutionthe resulting intermediate was dissolved in CH3CN (10 mL)
  8. extractionthe product was extracted with EtOAc
  9. washThe organic layer was washed with H2O and brine
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-a4fd630fa0b14cbe8d4a921cf2c29ccb
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

Loading…