Triethylamine → HCID 69080447, compound

HRID 2404997Notes

Reaction equation

HRID 2404997 reaction equation
[I:1][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]([CH2:33][CH2:34][CH2:35][C:36]#[CH:37])[C:21]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]=[C:23]([NH2:31])[C:22]=2[N:32]=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>[IH:1].[CH2:17]([C:19]1[N:20]([CH2:33][CH2:34][CH2:35][C:36]#[C:37][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]=[C:23]([NH2:31])[C:22]=2[N:32]=1)[CH3:18]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 696764-IodoanisoleHCID 86626645HCID 86626645, compound

Product 1

HCID 69080447HCID 69080447, 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 (0.095 g, 0.03 eq.), 4-iodoanisole (0.786 g, 1.1 eq.), triethylamine (1.3 mL, 3 eq.), and copper (I) iodide (0.035 g, 0.06 eq.) were added sequentially to a solution of 2-ethyl-1-(4-pentynyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.85 g, 3.0 mmol, 1.0 eq.) in DMF. The reaction mixture was stirred for about 4 hours and then concentrated under reduced pressure. The residue was purified by column chromatography (silica gel eluting with 4/96 methanol/dichloromethane) to provide an oil. The oil was recrystallized from ethanol to provide 2-ethyl-1-[5-(4-methoxyphenyl)-4-pentynyl]-1H-imidazo[4,5-c]quinolin-4-amine hydroiodide as off white granules, mp 230.0° C. 1H NMR (300 MHz, DMSO-d6) δ 13.14 (broad s, 1H), 8.65 (broad s, 2H), 8.37 (d, J=8.6 Hz, 1H), 7.83 (dd, J=8.4, 0.8 Hz, 1H), 7.68 (t, J=7.4 Hz, 1H), 7.41 (dt, J=8.1, 0.7 Hz, 1H), 7.34 (m, 2H), 6.93 (m, 2H), 4.73 (t, J=7.5 Hz, 2H), 3.77 (s, 3H), 3.08 (q, J=7.4 Hz, 2H), 2.66 (t, J=6.9 Hz, 2H), 2.09 (m, 2H), 1.41 (t, J=7.4 Hz, 3H); MS (APCI) m/z 385 (M+H)+; Anal. calcd for C24H24N4O1.HI.0.08C2H4Cl2: C, 55.30; H, 4.89; N, 10.69. Found: C, 55.39; H, 4.88; N, 10.63.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography (silica gel eluting with 4/96 methanol/dichloromethane)
  3. customto provide an oil
  4. customThe oil was recrystallized from ethanol

Sources & evidence

ORD record
ord-84e5539e8c764158a937505fb1d4e27f
Source dataset
uspto-grants-2014_08
Patent number
US08802853B2

Reaction notes

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