Triethylamine → HCID 69082291, compound

HRID 2404989Notes

Reaction equation

HRID 2404989 reaction equation
I[C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH2:18]([C:20]1[N:21]([CH2:34][C:35]#[CH:36])[C:22]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[C:24](N)[C:23]=2[N:33]=1)[CH3:19]>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>[CH2:18]([C:20]1[N:21]([CH2:34][C:35]#[C:36][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=2)[C:22]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[CH:24][C:23]=2[N:33]=1)[CH3:19]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 125741-Iodo-3-nitrobenzeneHCID 86626642HCID 86626642, compound

Product 1

HCID 69082291HCID 69082291, compoundYield 56.1%

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 (0.395 mg, 0.03 eq.), 3-iodonitrobenzene (3.5 g, 1.1 eq.), triethylamine (3.87 g, 3 eq.), and copper (I) iodide (0.145 g, 0.06 eq.) were added sequentially to a solution of 2-ethyl-1-(2-propynyl)-1H-imidazo[4,5-c]quinolin-4-amine (3 g, 13 mmol, 1.0 eq.) in DMF. The reaction mixture was stirred at ambient temperature for 3.5 hours. A precipitate was isolated by filtration and then recrystallized from dichloromethane to provide 2.6 g of 2-ethyl-1-[3-(3-nitrophenyl)-2-propynyl]-1H-imidazo[4,5-c]quinoline as a solid.

Workup

  1. customA precipitate was isolated by filtration
  2. customrecrystallized from dichloromethane

Sources & evidence

ORD record
ord-e633b47bf7514073a612d17155b305ad
Source dataset
uspto-grants-2014_08
Patent number
US08802853B2

Reaction notes

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