HCID 66922097, compound → HCID 66922203, compound

HRID 2039836Notes

Reaction equation

HRID 2039836 reaction equation
Br[C:2]1(Br)[C:6]2[CH:7]=[N:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=2[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]1=[O:19]>C(O)(=O)C.[Pd].[Zn]>[CH3:12][O:11][C:9]1[N:8]=[CH:7][C:6]2[CH2:2][C:3](=[O:19])[N:4]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:5]=2[CH:10]=1

Participants

5

Reactant 1

HCID 66922097HCID 66922097, compound

Product 1

HCID 66922203HCID 66922203, compoundYield 16.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 8.73 g of the compound of step 2 in acetic acid (180 ml) was added zinc, and the suspension was stirred at room temperature overnight. The mixture was extracted with EA, the organic layer was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. The resulting solid was dissolved in ethanol (245 ml), and palladium on activated carbon (1.75 g, 1.64 mmol, 10%) was added. The reaction mixture was hydrogenated (5.2 bar H2) at room temperature overnight. The mixture was filtered over celite, the solvent was removed under reduced pressure and the solid was purified by silica gel chromatography (EA (10 to 70%)/HEP). 870 mg of the title compound were obtained.

Workup

  1. extractionThe mixture was extracted with EA
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. dissolutionThe resulting solid was dissolved in ethanol (245 ml)
  7. customat room temperature
  8. customovernight
  9. filtrationThe mixture was filtered over celite
  10. customthe solvent was removed under reduced pressure
  11. customthe solid was purified by silica gel chromatography (EA (10 to 70%)/HEP)

Sources & evidence

ORD record
ord-2b75e856c37e4706b76466c7a7db5ad2
Source dataset
uspto-grants-2013_11
Patent number
US08580813B2

Reaction notes

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