1-Ethoxy-4-ethynylbenzene → 2-[(4-Ethoxyphenyl)ethynyl]-5-(methoxymethoxy)pyridine

HRID 1888752Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][N:3]=1.[CH2:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[CH:22])=[CH:17][CH:16]=1)[CH3:13].C1COCC1.C(N(CC)CC)C>C(OCC)(=O)C.[Cu]I.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>[CH2:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[C:22][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][N:3]=2)=[CH:17][CH:16]=1)[CH3:13]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-bromo-5-(methoxymethoxy)pyridine (2.50 g, 11.5 mmol), 1-ethoxy-4-ethynylbenzene (2.57 mL, 17.2 mmol) and copper(I) iodide (220 mg, 1.15 mmol) in a mixed solvent of THF-triethylamine (20 ml-10 mL) was added bis(triphenylphosphine)palladium(II) chloride (807 mg, 1.15 mmol), and the mixture was stirred under an argon stream at 60° C. for 15 min. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 3:7) to give the title compound (3.21 g, yield 98%) as a yellow solid.

Workup

washthe mixture was washed with water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 3:7)

Sources & evidence

ORD record: ord-65a431f3a1724f67973de712370d5e17
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501804B2

Reaction notes

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