Ethyl Acetate → HCID 23438493, compound

HRID 2120115Notes

Reaction equation

HRID 2120115 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Na].[NH:10]1[CH:14]=[N:13][CH:12]=[N:11]1.C(OCC)(=O)C>CN(C)C=O>[N:10]1([C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)[CH:14]=[N:13][CH:12]=[N:11]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 693532,5-DibromopyridineHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 23438493HCID 23438493, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml of dimethylformamide, 1 g of 2,5-dibromopyridin was reacted with 0.58 g of 1,2,4-triazole sodium at 80° C. for 10 hours with stirring. Following the addition of ethyl acetate, the organic layer thus separated was washed with brine, dehydrated, filtered, and concentrated in vacuo to give 880 mg of 2-(1,2,4-triazol-1-yl)-5-bromopyridine. This compound was dissolved, along with 1.4 g of (S)-[N-3-(4-trimethylstannyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl acetamide, in 50 ml of dimethylformamide and then added with 1.2 ml of triethyl amine and 1.1 g of dichlorobistriphenylphosphine palladium (II) at room temperature. Reaction was conducted at 100° C. for 3 hours. Water was then added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer thus separated was washed with brine, dehydrated, filtered, and concentrated in vacuo. Purification of the concentrate with column chromatography provided the title compound. 320 mg. Yield 23%.

Workup

  1. customthe organic layer thus separated
  2. washwas washed with brine
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6871d372da6e4f8186da2f801f907c18
Source dataset
uspto-grants-2004_02
Patent number
US06689779B2

Reaction notes

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