2-Bromopyridine → 2-(3-Methoxyprop-1-YN-1-YL)pyridine

HRID 2253370Notes

Reaction equation

HRID 2253370 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][O:9][CH2:10][C:11]#[CH:12]>C(NCC)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)I>[CH3:8][O:9][CH2:10][C:11]#[C:12][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 79732-BromopyridineHCID 693933-Methoxypropyne

Product 1

HCID 138648462-(3-Methoxyprop-1-YN-1-YL)pyridineYield 90.2%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-bromopyridine (20 g) dissolved in diethylamine (100 mL) was added 3-methoxy-1-propyne (11.8 g), dichlorobis(triphenylphosphine)palladium(II) (888 mg) and copper iodide (121 mg), and the reaction mixture was stirred for 1 hour at 40° C. under a nitrogen stream. After the reaction mixture was filtered through celite to remove insoluble residue, the filtrate was evaporated under reduced pressure, the residue was purified by silica gel column chromatography and the title compound (16.8 g) was obtained as a light orange oil from the n-hexane:ethyl acetate (5:1) fraction.

Workup

  1. filtrationAfter the reaction mixture was filtered through celite
  2. customto remove insoluble residue
  3. customthe filtrate was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-49b1cbd7411146cb9b30c62f45893773
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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