2,6-Dibromopyridine → HCID 19966486, compound

HRID 977600Notes

Reaction equation

HRID 977600 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[CH3:9][O:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[CH:19])[CH:13]=1>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:19]#[C:18][C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([O:10][CH3:9])=[O:20])[CH:13]=2)[N:3]=1

Participants

6

Reactant 2

HCID 122742,6-DibromopyridineHCID 112751593-Ethynylbenzoic acid methyl ester

Product 1

HCID 19966486HCID 19966486, compoundYield 23.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 15.1 g of 2,6-dibromopyridine in 500 ml of triethylamine is mixed under ice cooling with 10.2 g of 3-ethinylbenzoic acid methyl ester, 1.1 g of bis-(triphenylphosphine)-palladium(II) chloride and 150 mg of copper(I) iodide and the mixture is stirred for 1 hour. Then, the ice bath is removed and it is stirred for 48 hours at room temperature. The precipitate is filtered off, the filtrate is evaporated to dryness, mixed with water and shaken out with ethyl acetate. The organic phase is dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/0-12% ethyl acetate. 4.8 g of 2-bromo-6-[2-(3-methoxycarbonyiphenyl)-ethinyl]-pyridine of melting point 12°-126° C. is obtained.

Workup

  1. customThen, the ice bath is removed
  2. stirringit is stirred for 48 hours at room temperature
  3. filtrationThe precipitate is filtered off
  4. customthe filtrate is evaporated to dryness
  5. additionmixed with water
  6. stirringshaken out with ethyl acetate
  7. customThe organic phase is dried on sodium sulfate
  8. concentrationconcentrated by evaporation
  9. customthe residue is chromatographed on silica gel with hexane/0-12% ethyl acetate

Sources & evidence

ORD record
ord-4bb28497933843ff97b13aab94eb29fe
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Reaction notes

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