Triethylamine → HCID 18760173, compound

HRID 432692Notes

Reaction equation

HRID 432692 reaction equation
[N:1]1([CH2:14][CH2:15][O:16][CH2:17][C:18]#[CH:19])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.C(N(CC)CC)C.I[C:28]1[S:29][CH:30]=[CH:31][CH:32]=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.CN(C)C=O>[S:29]1[CH:30]=[CH:31][CH:32]=[C:28]1[C:19]#[C:18][CH2:17][O:16][CH2:15][CH2:14][N:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 189212-IodothiopheneHCID 12114205HCID 12114205, compound

Product 1

HCID 18760173HCID 18760173, compoundYield 60.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A dried round bottom flask was charged with a stir bar, 2-(1H-imidazo[4,5-c]quinolin-1-yl)ethyl (2-propynyl)ether (11.78 g, 46.88 mmol), anhydrous triethylamine (14 mL, 121.9 mmol), 2-iodothiophene (5.7 mL, 51.57 mmol) and anhydrous dimethyl formamide(130 mL) under a nitrogen atmosphere and heated to 80° C. After 5 minutes dichlorobis(triphenylphosphine)palladium(II) (0.658 g, 0.937 mol) and copper(I) iodide (0.357 g, 1.875 mmol) were added neat to the solution. The reaction was judged complete after 50 minutes. The volatiles were removed under reduced pressure and the resulting solid partitioned between dichloromethane and 0.5N aqueous potassium hydroxide. The aqueous fraction was extracted with dichloromethane (3×); the combined organic fractions were dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to provide a brown solid. The glassy solid obtained from purification by chromatography over silica gel (98/2 dichloromethane/methanol) was triturated with ether to provide 9.5 g of 1-{2-[(3-thien-2-ylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinolin as a tan solid.

Workup

  1. additionA dried round bottom flask was charged with a stir bar
  2. customThe volatiles were removed under reduced pressure
  3. customthe resulting solid partitioned between dichloromethane and 0.5N aqueous potassium hydroxide
  4. extractionThe aqueous fraction was extracted with dichloromethane (3×)
  5. dry with materialthe combined organic fractions were dried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto provide a brown solid
  9. customThe glassy solid obtained from purification by chromatography over silica gel (98/2 dichloromethane/methanol)
  10. customwas triturated with ether

Sources & evidence

ORD record
ord-a611a2df43c94f82887a171d21c730a3
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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