Triethylamine → HCID 69084239, compound

HRID 2404985Notes

Reaction equation

HRID 2404985 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:17]([C:19]1[N:20]([CH2:32][C:33]#[CH:34])[C:21]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]=[CH:23][C:22]=2[N:31]=1)[CH3:18]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].[Cu]I>[CH2:17]([C:19]1[N:20]([CH2:32][C:33]#[C:34][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[C:21]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]=[CH:23][C:22]=2[N:31]=1)[CH3:18]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 696764-IodoanisoleHCID 86626641HCID 86626641, compound

Product 1

HCID 69084239HCID 69084239, compoundYield 48.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 6228DimethylformamideSolvent

Procedure

Tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (64 mg, 0.03 eq.), 4-iodoanisole (531 mg, 1.1 eq.), triethylamine (862 μL, 3.0 eq.), and copper (I) iodide (23.6 mg, 0.06 eq.) were added sequentially to a solution of 2-ethyl-1-(2-propynyl)-1H-imidazo[4,5-c]quinoline (485 mg, 2.06 mmol, 1.0 eq.) in DMF (10 mL). The reaction mixture was stirred at ambient temperature for 3 hour and then concentrated under reduced pressure. The residue was purified by column chromatography (silica gel eluting with 2/98 methanol/chloroform) to provide 0.34 g of 2-ethyl-1-[3-(4-methoxyphenyl)-2-propynyl]-1H-imidazo[4,5-c]quinoline as a clear oil that partially crystallized on standing.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography (silica gel eluting with 2/98 methanol/chloroform)

Sources & evidence

ORD record
ord-11d66dd5e5934181a89899603d3324d4
Source dataset
uspto-grants-2014_08
Patent number
US08802853B2

Reaction notes

Loading…