2,5-Dibromopyridine → 5-Bromo-2-(3-methoxy-prop-1-ynyl)-pyridine

HRID 1814464Notes

Reaction equation

HRID 1814464 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH2:9]([O:12][CH3:13])[C:10]#[CH:11]>C(N(CC)CC)C.[Cu](I)I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:11]#[C:10][CH2:9][O:12][CH3:13])=[N:3][CH:4]=1

Participants

6

Reactant 2

HCID 693532,5-DibromopyridineHCID 693933-Methoxypropyne

Product 1

HCID 225032615-Bromo-2-(3-methoxy-prop-1-ynyl)-pyridineYield 79%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

2,5-Dibromopyridine (16.582 g) was dissolved in triethylamine (200 ml), followed by the addition of methyl propargyl ether (5.9 ml), copper iodide (267 mg) and bis(triphenylphosphine)palladium (II) chloride (46 mg). The resulting mixture was stirred in nitrogen atmosphere at room temperature for 1 hr. Subsequently, it was stirred at room temperature for further 3 hr. After the resulting insoluble matters were filtered off, the resulting solution was evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a brown solid (12.411 g, yield; 79%).

Workup

  1. stirringSubsequently, it was stirred at room temperature for further 3 hr
  2. filtrationAfter the resulting insoluble matters were filtered off
  3. customthe resulting solution was evaporated
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-4a310222aa7542eea614433a2f3202c5
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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