Acetonitrile → 3-(2-Methyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl (3-Phenylprop-2-ynyl) Ether

HRID 1839133Notes

Reaction equation

HRID 1839133 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=[C:9]1[CH3:21])[C:2]#[CH:3].C(#N)C.C(N(CC)CC)C.I[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.CCOCC>[C:33]1([C:3]#[C:2][CH2:1][O:4][CH2:5][CH2:6][CH2:7][N:8]2[C:20]3[C:19]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[N:13]=[CH:12][C:11]=3[N:10]=[C:9]2[CH3:21])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 11575IodobenzeneHCID 858834993-(2-Methyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl (Prop-2-ynyl) Ether

Product 1

HCID 222544103-(2-Methyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl (3-Phenylprop-2-ynyl) EtherYield 79.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere, a mixture of 3-(2-methyl-1H-Imidazo[4,5-c]quinolin-1-yl)propyl (prop-2-ynyl) ether (4.6585 g, 16.68 mmol) from Part A, anhydrous acetonitrile (60 mL), anhydrous triethylamine (6 mL, 43.37 mmol), and iodobenzene (2.1 mL, 18.34 mmol) was heated to 80° C. with stirring. Dichlorobis(triphenylphosphine)palladium(II) (0.23 g, 0.334 mmol), and copper(I) iodide (0.13 g, 0.667 mmol) were added and the mixture was allowed to stir for 0.5 hour. Analysis by HPLC indicated that the reaction was complete. The reaction mixture was concentrated under reduced pressure, and the concentrate was purified by column chromatography over silica gel, employing dichloromethane (1 L) and 98/2 dichloromethane/methanol as the eluants. The resulting green oil (5.1 g) was triturated with ether, but no solids formed. The oil was placed under high vacuum (4 torr) at room temperature. HNMR analysis of the resulting oil showed the presence of ether. The oil was further dried under high vacuum to provide 4.7 g of dark oil.

Workup

  1. stirringto stir for 0.5 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe concentrate was purified by column chromatography over silica gel
  4. customThe resulting green oil (5.1 g) was triturated with ether
  5. customno solids formed
  6. customwas placed under high vacuum (4 torr) at room temperature
  7. customThe oil was further dried under high vacuum

Sources & evidence

ORD record
ord-f1903389ee4848c588951c808d5939d8
Source dataset
uspto-grants-2004_01
Patent number
US06677348B2

Reaction notes

Loading…