Triethylamine → HCID 69080743, compound

HRID 2404984Notes

Reaction equation

HRID 2404984 reaction equation
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:20]([C:22]1[N:23]([CH2:35][C:36]#[CH:37])[C:24]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[CH:26][C:25]=2[N:34]=1)[CH3:21]>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>[CH2:20]([C:22]1[N:23]([CH2:35][C:36]#[C:37][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[C:24]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[CH:26][C:25]=2[N:34]=1)[CH3:21]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 142891Ethyl 4-iodobenzoateHCID 86626641HCID 86626641, compound

Product 1

HCID 69080743HCID 69080743, compound

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 (65.9 mg, 0.03 eq.), ethyl 4-iodobenzoate (388 μL, 1.1 eq.), triethylamine (887 μL, 3.0 eq.), and copper (I) iodide (24.2 mg, 0.06 eq.) were added sequentially to a solution of 2-ethyl-1-(2-propynyl)-1H-imidazo[4,5-c]quinoline (499 mg, 2.12 mmol, 1.0 eq.) in DMF (10.6 mL). The reaction mixture was stirred at ambient temperature for 1 hour and then concentrated under reduced pressure. The residue was purified by column chromatography (silica gel eluting with 5/95 methanol/chloroform) to provide 0.70 g of ethyl 4-[3-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-propynyl]benzoate as a light tan solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography (silica gel eluting with 5/95 methanol/chloroform)

Sources & evidence

ORD record
ord-64da3cb534564edf9071fe51a3895910
Source dataset
uspto-grants-2014_08
Patent number
US08802853B2

Reaction notes

Loading…