Ammonium Chloride → HCID 91454878, compound

HRID 857345Notes

Reaction equation

HRID 857345 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[Br:7][C:8]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]2[C:9]=1[C:10]([S:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)=[C:11]1[C:21](=[O:22])[CH2:20][CH2:19][CH2:18][N:12]12.[NH4+].[Cl-]>C1COCC1.[Zn].[Cu]>[Br:7][C:8]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]2[C:9]=1[C:10]([S:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)=[C:11]1[C:21]([CH2:2][C:3]([O:5][CH3:6])=[O:4])([OH:22])[CH2:20][CH2:19][CH2:18][N:12]12

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 21867462HCID 21867462, compound

Product 1

HCID 91454878HCID 91454878, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 10290809Zinc copper coupleCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a boiling suspension of 300 mg of Zn-copper couple in 4 mL of THF was added dropwise methyl bromoacetate (720 mg, 4.7 mmol). The suspension was stirred at reflux for 30 minutes and a solution of the ketone of Step 4 (200 mg, 0.5 mmol) in THF (1 mL) was added. The reaction mixture was stirred at reflux for 5 h and saturated aqueous NH4Cl solution was added and extracted with EtOAc. The combined organic layers were washed with brine and water, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 20% EtOAc in Hexanes to provide 106 mg of the title compound as a pale brown solid.

Workup

  1. temperatureat reflux for 30 minutes
  2. stirringThe reaction mixture was stirred
  3. temperatureat reflux for 5 h
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine and water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluted with 20% EtOAc in Hexanes

Sources & evidence

ORD record
ord-99faf79565874c3ab0afe7cb83e6fb98
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

Loading…