Sodium Formate → HCID 20777476, compound

HRID 1816608Notes

Reaction equation

HRID 1816608 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12](=[O:14])[O-:13])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH:15]([O-:17])=O.[Na+].[C]=O>CN(C)C=O.C(OCC)(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:15]([C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12](=[O:14])[O:13][C:4]([CH3:10])([CH3:5])[CH3:3])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1)=[O:17]

Participants

7

Reactant 3

HCID 2723810Sodium FormateHCID 86759681HCID 86759681, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 20777476HCID 20777476, compoundYield 77.6%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.009 g of N-[(5-bromo-2-methoxy-3-pyridyl)methyl]carbamate, 45 mg of dichlorobistriphenylphosphine palladium, 325 mg of sodium formate and 17 mg of triphenylphosphine were dissolved in 3 ml anhydrous N,N-dimethylformamide, followed by stirring at 110° C. for 2.5 hours in a carbon monoxide atmosphere. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water and saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 401 mg of tertiary butyl N-[(5-formyl-2-methoxy-3-pyridyl)methyl]carbamate was obtained from fractions eluted with hexane-ethyl acetate (3.5:1).

Workup

  1. washthe organic layer was washed with water and saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cdfbcee0e0e747e69db7eb375ba6a042
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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