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

HRID 1006893Notes

Reaction equation

HRID 1006893 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-615b514faf0f41169674b60162d6e3d2
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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