Sodium Acetate → HCID 67223823, compound

HRID 1947641Notes

Reaction equation

HRID 1947641 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:3]=1[C:4]([N:6]([CH2:11][CH3:12])[CH2:7][C:8]([CH3:10])=[CH2:9])=[O:5].C([O-])=O.[Na+].C([O-])(=O)C.[Na+]>[Cl-].C([N+](CC)(CC)CC)C.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:11]([N:6]1[CH2:7][C:8]([CH3:10])([CH3:9])[C:2]2[C:3](=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)[C:4]1=[O:5])[CH3:12]

Participants

7

Reactant 3

HCID 517045Sodium AcetateHCID 2723810Sodium FormateHCID 61945180HCID 61945180, compound

Product 1

HCID 67223823HCID 67223823, compoundYield 96.3%

Reagents, catalysts & solvents 3

HCID 5946Tetraethylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred de-gassed solution of 2-bromo-N-ethyl-N-(2-methyl-allyl)-5-nitro-benzamide (150 mg, 0.46 mmol), tetra-ethylammonium chloride (84 mg, 0.46 mmol), sodium formate (34 mg, 0.50 mmol) and sodium acetate (82 mg, 1.01 mmol) in anhydrous DMF (10 ml) was added palladium(II) acetate (10 mg, 0.046 mmol) and the reaction stirred at 70° C. for 15 hrs. The reaction was cooled to room temperature and filtered through a pad of celite. The solvent was evaporated in vacuo and the resulting residue purified by flash column chromatography (20% ethyl acetate in dichloromethane) to afford the title compound as a yellow solid (110 mg, 96%). HPLC retention time 4.21 min. Mass spectrum (ES+) m/z 249 (M+H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. customThe solvent was evaporated in vacuo
  4. customthe resulting residue purified by flash column chromatography (20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-c7505c8923654caa9491e411e87e844b
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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