Sodium Formate → HCID 86611467, compound

HRID 452491Notes

Reaction equation

HRID 452491 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:7])=[C:4]([CH3:18])[CH:3]=1.[CH:19]([O-])=[O:20].[Na+].[C]=O>CN(C)C=O.O>[CH:19]([C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:7])=[C:4]([CH3:18])[CH:3]=1)=[O:20]

Participants

6

Reactant 3

HCID 2723810Sodium FormateHCID 47265314HCID 47265314, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 86611467HCID 86611467, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a solution of 2.0 g of 4-bromo-2-methyl-N-(2-pyridylmethyl)benzoic acid amide in 20 ml of N,N-dimethylformamide in an autoclave, 0.67 g of sodium formate and 0.10 g of dichlorobis(triphenylphosphine) palladium (II) were added, and stirred under 1.05 MPa carbon monoxide atmosphere at 110° C. for 3 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and poured in 100 ml of water, and extracted with ethyl acetate (50 ml×2). The organic phases together were dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (9:1), and 0.50 g of the aimed product was obtained as pale yellow crystal.

Workup

  1. customAfter the completion of the reaction
  2. waitthe reaction mixture was left
  3. extractionextracted with ethyl acetate (50 ml×2)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-050dbe76f3374e98a1ee936abd9d6435
Source dataset
uspto-grants-2013_07
Patent number
US08492311B2

Reaction notes

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