Iodobenzene → HCID 22254423, compound

HRID 433992Notes

Reaction equation

HRID 433992 reaction equation
[CH3:1][C:2]1[N:3]([CH2:15][CH2:16][O:17][CH2:18][C:19]#[CH:20])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=1.I[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)(O)[O-].[Na+]>>[CH3:1][C:2]1[N:3]([CH2:15][CH2:16][O:17][CH2:18][C:19]#[C:20][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=1

Participants

4

Reactant 3

HCID 11575IodobenzeneHCID 516892Sodium BicarbonateHCID 22254462HCID 22254462, compound

Product 1

HCID 22254423HCID 22254423, compoundYield 41.9%

Procedure

Using the general method of Example 12 Part A, 2-methyl-1-[2-(prop-2-ynyloxy)ethyl]-1H-imidazo[4,5-c]quinoline (3.6 g, 13.57 mmol) was reacted with iodobenzene (1.7 mL, 14.92 mmol) at ambient temperature. After 20 hours the reaction was judged complete. The solution was basified with 5% aqueous sodium bicarbonate and then extracted with dichloromethane (3×). The organics were combined, washed with water (3×), washed with brine, dried with anhydrous sodium sulfate, filtered and then concentrated under reduced pressure. Purification was completed by chromatography over silica gel (95/5 dichloromethane/methanol) and recrystallization from acetonitrile to provide 1.94 g of 2-methyl-1-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinoline as a light yellow solid.

Workup

  1. extractionextracted with dichloromethane (3×)
  2. washwashed with water (3×)
  3. washwashed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification
  8. customwas completed by chromatography over silica gel (95/5 dichloromethane/methanol) and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-8fe114eb5f244553b901c6ff3d9c8bf2
Source dataset
uspto-grants-2003_12
Patent number
US06670372B2

Reaction notes

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