Trimethyl orthovalerate → 7-bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinoline

HRID 1818100Notes

Reaction equation

HRID 1818100 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:18](OC)(OC)(OC)[CH2:19][CH2:20][CH2:21][CH3:22]>Cl.N1C=CC=CC=1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:18]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 83755Trimethyl orthovalerateHCID 688181597-bromo-N4-isobutylquinoline-3,4-diamine

Product 1

HCID 219843597-bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinolineYield 43.9%

Reagents, catalysts & solvents 2

HCID 10176127Pyridinium chlorideCatalystHCID 1140TolueneSolvent

Procedure

7-Bromo-N4-isobutylquinoline-3,4-diamine (39.4 g of crude material), trimethyl orthovalerate (32 g, 0.20 mol), and pyridine hydrochloride (0.31 g, 2.7 mmol) were combined with anhydrous toluene (500 mL) and heated to reflux for 30 min. The reaction was cooled to room temperature, concentrated, and the residue was purified by chromatography on silica gel (75% ethyl acetate in hexane to 100% ethyl acetate gradient) to afford 21.2 g of 7-bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinoline as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 min
  3. concentrationconcentrated
  4. customthe residue was purified by chromatography on silica gel (75% ethyl acetate in hexane to 100% ethyl acetate gradient)

Sources & evidence

ORD record
ord-2ce973852df043cb9ceeab06a2d77bfa
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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