1-Butyne → 2-(1-Butynyl)-4-methoxypyridine

HRID 9186

Reaction equation

HRID 9186 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=CC=CN=1.[CH:10]#[C:11][CH2:12]C.[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15]>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)I>[C:15]([C:14]1[CH:2]=[C:7]([O:8][CH3:9])[CH:18]=[CH:17][N:16]=1)#[C:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 78461-ButyneHCID 8021DiethylamineHCID 903642-Bromo-3-methoxypyridine

Product 1

HCID 219846612-(1-Butynyl)-4-methoxypyridine

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

After adding dichlorobis(triphenylphosphine)palladium (II) (671 mg) and copper iodide (91 mg) to a solution of 2-bromo-3-methoxypyridine (18.0 g) in diethylamine (250 mL), 1-butyne (15.5 g) was bubbled through at room temperature, and the mixture was stirred for 20 hours. Upon completion of the reaction, the solvent was distilled off under reduced pressure. Water was added to the obtained residue, extraction was performed with ethyl acetate, the extract was washed with brine and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography (500 g), and 2-(1-butynyl)-4-methoxypyridine (10.0 g) was obtained from the n-hexane:ethyl acetate (2:1) fraction as a brown oil.

Workup

  1. customwas bubbled through at room temperature
  2. customUpon completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionWater was added to the obtained residue, extraction
  5. washthe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c955a68fd91c4d9193e9298121138839
Source dataset
uspto-grants-2006_08
Patent number
US07091215B2

Linked notes

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