Sodium Formate → HCID 86611467, compound

HRID 1844820Notes

Reaction equation

HRID 1844820 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-05df5ee8b6f3451e84edc659427c8610
Source dataset
uspto-grants-2015_02
Patent number
US08946492B2

Reaction notes

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