Sodium Acetate → HCID 67442191, compound

HRID 2096273Notes

Reaction equation

HRID 2096273 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([N:9]([CH2:21][C:22]#[C:23][C:24]2[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=2)[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[O:19][CH3:20])=[O:8])[NH:5][CH:6]=1.C([O-])(=O)C.[Na+]>CS(C)=O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:7](=[O:8])[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=3[O:19][CH3:20])[CH:21]=[C:22]([CH2:23][C:24]3[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=3)[C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:5]2[CH:6]=1

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 67441517HCID 67441517, compound

Product 1

HCID 67442191HCID 67442191, compound

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of EXAMPLE 4B (100 mg, 0.2 mmol) in dimethylsulfoxide (3 mL) was added sodium acetate (16 mg, 0.2 mmol), tetra-n-butylammonium chloride (53 mg, 0.2 mmol) and palladium(II) acetate (4.3 mg, 0.02 mmol). The mixture was stirred at 80° C. for 10 minutes. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and diluted aqueous HCl solution. The organic phase was washed with water, NaHCO3 solution, and brine, and concentrated. The residue was separated by flash chromatography eluting with ethyl acetate to afford the title compound. MS (DCI/NH3) m/z 526 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between ethyl acetate and diluted aqueous HCl solution
  3. washThe organic phase was washed with water, NaHCO3 solution, and brine
  4. concentrationconcentrated
  5. customThe residue was separated by flash chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-db1221d307b0414e93799d65e2d2a9df
Source dataset
uspto-grants-2013_05
Patent number
US08450320B2

Reaction notes

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