Ethyl orthoformate → 9-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

HRID 1818221Notes

Reaction equation

HRID 1818221 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([NH:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[C:5]([NH2:12])[CH:6]=[N:7]2.[CH:18](OCC)(OCC)OCC.Cl.N1C=CC=CC=1>C(#N)C>[Br:1][C:2]1[C:3]2[C:4]3[N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH:18]=[N:12][C:5]=3[CH:6]=[N:7][C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 10176127Pyridinium chlorideHCID 68819348HCID 68819348, compound

Product 1

HCID 219843489-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromo-N4-(2-methylpropyl)quinoline-3,4-diamine (1.0 g, 3.4 mmol), triethyl orthoformate (0.9 mL, 5 mmol), and pyridine hydrochloride (117 mg, 1.0 mmol) in acetonitrile (17 mL) was heated at reflux overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by HPFC (eluting with chloroform:CMA in a gradient from 100:0 to 70:30) to provide 9-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline as a dark oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by HPFC (
  5. washeluting with chloroform

Sources & evidence

ORD record
ord-9f45d54f6e4449de8bf5b456473bd16d
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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