Iodobenzene → 2-(ethoxymethyl)-1-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinoline

HRID 1839115Notes

Reaction equation

HRID 1839115 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][O:20][CH2:21][C:22]#[CH:23])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].I[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][O:20][CH2:21][C:22]#[C:23][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2]

Participants

3

Reactant 2

HCID 11575IodobenzeneHCID 222544792-(ethoxymethyl)-1-[2-(prop-2-ynyloxy)ethyl]-1H-imidazo[4,5-c]quinoline

Product 1

HCID 222544292-(ethoxymethyl)-1-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinolineYield 78.5%

Procedure

Using the general method of Example 12 Part A, 2-(ethoxymethyl)-1-[2(prop-2-ynyloxy)ethyl]-1H-imidazo[4,5-c]quinoline (1.5 g, 4.13 mmol) was reacted with iodobenzene (0.51 mL, 4.54 mmol) at 40° C. After 50 minutes the reaction was judged complete. The volatiles were removed under reduced pressure and the resulting oil was partitioned between dichloromethane and 5% aqueous sodium bicarbonate. The aqueous layer was extracted with dichioromethane. The organic fractions were combined, washed with brine, dried with anhydrous sodium sulfate, and then concentrated under reduced pressure to leave a brown oil. The oil was purified by chromatography over silica gel (98/2 dichloromethane/methanol) to provide 1.25 g of 2-(ethoxymethyl)-1-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinoline as a brown glassy solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe resulting oil was partitioned between dichloromethane and 5% aqueous sodium bicarbonate
  3. extractionThe aqueous layer was extracted with dichioromethane
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto leave a brown oil
  8. customThe oil was purified by chromatography over silica gel (98/2 dichloromethane/methanol)

Sources & evidence

ORD record
ord-0e8a06b3b7cb424bb0d601928d234e80
Source dataset
uspto-grants-2004_01
Patent number
US06677348B2

Reaction notes

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