Bromine → 8-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9366

Reaction equation

HRID 9366 reaction equation
[CH2:1]([N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:18])[C:8]=2[N:7]=[CH:6]1)[CH:2]([CH3:4])[CH3:3].[Br:19]Br>C(O)(=O)C>[Br:19][C:14]1[CH:13]=[CH:12][C:11]2[N:10]=[C:9]([NH2:18])[C:8]3[N:7]=[CH:6][N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:17]=3[C:16]=2[CH:15]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 57469Imiquimod

Product 1

HCID 111745978-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amineYield 25.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine (10.0 g, 41.6 mmol) in acetic acid (150 mL) was added Br2 (10.0 g, 62.6 mmol), and after 24 h, the resulting solid was collected by filtration and washed with H2O. The orange solid was suspended in a saturated aqueous solution of NaHSO3, after which it was again collected and stirred with a 2 M solution of Na2CO3 for 18 h. The solid was collected by filtration, washed with H2O, and azeotropically dried with toluene on a rotary evaporator. Purification on silica gel (7%–10% methanol in CH2Cl2 gradient) afforded 3.4 g of 8-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with H2O
  3. customafter which it was again collected
  4. filtrationThe solid was collected by filtration
  5. washwashed with H2O
  6. dry with materialazeotropically dried with toluene on a rotary evaporator
  7. customPurification on silica gel (7%–10% methanol in CH2Cl2 gradient)

Sources & evidence

ORD record
ord-ed8f627f3e2042acae8a94dcfcac827a
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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