Triethylamine → HCID 57557246, compound

HRID 2404995Notes

Reaction equation

HRID 2404995 reaction equation
I[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.C(N(CC)CC)C.[CH2:14]([C:16]1[N:17]([CH2:30][CH2:31][CH2:32][C:33]#[CH:34])[C:18]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[C:20]([NH2:28])[C:19]=2[N:29]=1)[CH3:15]>ClCCl.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>[CH2:14]([C:16]1[N:17]([CH2:30][CH2:31][CH2:32][C:33]#[C:34][C:2]2[S:3][CH:4]=[CH:5][CH:6]=2)[C:18]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[C:20]([NH2:28])[C:19]=2[N:29]=1)[CH3:15]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 189212-IodothiopheneHCID 86626645HCID 86626645, compound

Product 1

HCID 57557246HCID 57557246, compoundYield 19.8%

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 6344DichloromethaneSolvent

Procedure

Tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (0.112 g, 0.03 eq.), 2-iodothiophene (3.9 g, 1.1 eq.), triethylamine (1.1 g, 3 eq.), and copper (I) iodide (0.042 g, 0.06 eq.) were added sequentially to a solution of 2-ethyl-1-(4-pentynyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.0 g, 3.5 mmol, 1.0 eq.) in dichloromethane (20 mL). The reaction mixture was stirred at ambient temperature for 6 hours at which time analysis by liquid chromatography/mass spectroscopy indicated that the reaction was complete. The reaction mixture was absorbed onto the top of a column of silica gel (30 g) and the column was eluted sequentially with dichloromethane and 3/97 methanol/dichloromethane. The product was recrystallized from 1,2-dichloroethane to provide 0.25 g of 2-ethyl-1-[5-(thien-2-yl)-4-pentynyl]-1H-imidazo[4,5-c]quinolin-4-amine as an off white powder, mp 175.0-190.0° C. (dec.). 1H NMR (300 MHz, CDCl3) δ 8.09 (dd, J=8.3, 1.0 Hz, 1H), 7.82 (dd, J=8.3, 1.0 Hz, 1H), 7.48 (ddd, J=8.4, 6.9, 1.3 Hz, 1H), 7.24 (m, 3H), 6.99 (dd, J=5.1, 3.6 Hz, 1H), 5.37 (s, 2H), 4.65 (t, J=7.7 Hz, 2H), 3.01 (q, J=7.5 Hz, 2H), 2.63 (t, J=6.2 Hz, 2H), 2.23 (m, 2H), 1.49 (t, J=7.4 Hz, 3H); MS (APCI) m/z 361 (M+H)+; Anal. calcd for C21H20N4S.0.03C2H4Cl2: C, 69.88; H, 5.59; N, 15.51. Found: C, 69.59; H, 5.69; N, 15.34.

Workup

  1. customThe reaction mixture was absorbed onto the top of a column of silica gel (30 g)
  2. washthe column was eluted sequentially with dichloromethane and 3/97 methanol/dichloromethane
  3. customThe product was recrystallized from 1,2-dichloroethane

Sources & evidence

ORD record
ord-150e70ebf7764cdca323f2482fea1067
Source dataset
uspto-grants-2014_08
Patent number
US08802853B2

Reaction notes

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