Dimethylformamide → HCID 12114211, compound

HRID 433970

Reaction equation

HRID 433970 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[CH:8]1)[C:2]#[CH:3].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].F[C:33](F)(F)[C:34](O)=O>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.C(#N)C.O>[C:34]1([C:3]#[C:2][CH2:1][O:4][CH2:5][CH2:6][N:7]2[C:19]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[N:12]=[C:11]([NH2:20])[C:10]=3[N:9]=[CH:8]2)[CH:33]=[CH:18][CH:19]=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 98566101-[2-(2-propynyloxy)ethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 12114211HCID 12114211, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
85 °C

Procedure

Under a nitrogen atmosphere, a mixture of 1-[2-(2-propynyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (10 g, 37.6 mmol), anhydrous N,N-dimethylformamide (150 mL) and potassium carbonate (6.23 g, 45.1 mmol) was heated to 70° C. lodobenzene (4.43 mL, 39.5 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.53 g, 0.75 mol), and copper(I) iodide (0.29 g, 1.50 mmol) were added and the mixture was allowed to stir for 0.5 hour. The temperature was raised to about 85° C. After 1.5 hours analysis by HPLC (reverse phase, acetonitrile/water with 0.1% trifluoroacetic acid) indicated that the reaction was complete. The mixture was allowed to cool to ambient temperature and then it was filtered. The filtrate was concentrated under reduced pressure. The residue was purified twice by flash chromatography (95/5 dichloromethane/methanol) to provide 2.7 g of 1-{2-[(3-phenyl-2-propynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, m.p. 196-197° C.

Workup

  1. additionwere added
  2. temperatureto cool to ambient temperature
  3. filtrationit was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified twice by flash chromatography (95/5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-d5a4024a39d344898ec0b79911be0166
Source dataset
uspto-grants-2003_12
Patent number
US06670372B2

Linked notes

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