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

HRID 9350

Reaction equation

HRID 9350 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-162be3fc5e3f4ed98a5683cec7677ead
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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