Triethylamine → 3-[(6-Methylpyridin-2-yl)ethynyl]cyclohex-2-en-1-one

HRID 1189052Notes

Reaction equation

HRID 1189052 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[N:4]=1)#[CH:2].Br[C:11]1[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH:12]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)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>[CH3:9][C:5]1[N:4]=[C:3]([C:1]#[C:2][C:11]2[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH:12]=2)[CH:8]=[CH:7][CH:6]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 109650383-Bromocyclohex-2-enoneHCID 134006352-Ethynyl-6-methylpyridine

Product 1

HCID 689367313-[(6-Methylpyridin-2-yl)ethynyl]cyclohex-2-en-1-oneYield 82.8%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-ethynyl-6-methyl-pyridine (702 mg, 6 mmol), 3-bromo-cyclohex-2-enone (1.26 g, 7.2 mmol), bis-(triphenylphosphine)palladium-dichloride (168 mg, 0.24 mmol), copper(I) iodide (93 mg, 0.48 mmol), triethylamine (4.8 ml, 34.4 mmol) in 12 ml DMF is heated to 55° C. for 1 h. After that time the solution is diluted with ethyl acetate (500 ml) and washed with sat aq. NaHCO3 (1×150 ml). The water phase is extracted with ethyl acetate (1×150 ml) and the combined organic phases are dried over Na2SO4, filtered and concentrated in vacuo. The residue (1.88 g) is purified on column chromatography (silica gel, eluent hexane/ethyl acetate 3:1 v/v) and the fractions containing the desired compound are collected and concentrated in vacuo to yield 1.05 g (yield=82%) of the title compound as a light yellow oil.

Workup

  1. washwashed
  2. extractionThe water phase is extracted with ethyl acetate (1×150 ml)
  3. dry with materialthe combined organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue (1.88 g) is purified on column chromatography (silica gel, eluent hexane/ethyl acetate 3:1 v/v)
  7. additionthe fractions containing the desired compound
  8. customare collected
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e185eab347a4bbc940486f1adf7ff8f
Source dataset
uspto-grants-2014_03
Patent number
US08674110B2

Reaction notes

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