4-Propoxyphenylboronic Acid → 2-butyl-1-isobutyl-7-(4-propoxyphenyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9353Notes

Reaction equation

HRID 9353 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:14]([CH2:20][CH2:21][CH2:22][CH3:23])=[N:13][C:7]=3[C:8]([NH2:12])=[N:9][C:10]=2[CH:11]=1.[CH2:24]([O:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)[CH2:25][CH3:26]>>[CH2:20]([C:14]1[N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:6]2[C:5]3[CH:4]=[CH:3][C:2]([C:31]4[CH:32]=[CH:33][C:28]([O:27][CH2:24][CH2:25][CH3:26])=[CH:29][CH:30]=4)=[CH:11][C:10]=3[N:9]=[C:8]([NH2:12])[C:7]=2[N:13]=1)[CH2:21][CH2:22][CH3:23]

Participants

3

Reactant 2

HCID 44564904-Propoxyphenylboronic AcidHCID 688179447-Bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 219841702-butyl-1-isobutyl-7-(4-propoxyphenyl)-1H-imidazo[4,5-c]quinolin-4-amine

Procedure

7-Bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and 4-propoxybenzeneboronic acid were coupled according to the general procedure described in Part J of Example 1. The product was recrystallized from isopropanol, collected by filtration, dissolved in CH2Cl2, and then precipitated with hexanes to afford 2-butyl-1-isobutyl-7-(4-propoxyphenyl)-1H-imidazo[4,5-c]quinolin-4-amine as a pale yellow solid, m.p. 194–197° C.

Workup

  1. customThe product was recrystallized from isopropanol
  2. filtrationcollected by filtration
  3. dissolutiondissolved in CH2Cl2
  4. customprecipitated with hexanes

Sources & evidence

ORD record
ord-182ec36ce0ca4c7dba7b593a28732964
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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