Phenylboronic Acid → 1-isobutyl-8-phenyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9371Notes

Reaction equation

HRID 9371 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]([NH2:12])[C:6]3[N:13]=[CH:14][N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:5]=3[C:4]=2[CH:3]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:16]([N:15]1[C:5]2[C:4]3[CH:3]=[C:2]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:11]=[CH:10][C:9]=3[N:8]=[C:7]([NH2:12])[C:6]=2[N:13]=[CH:14]1)[CH:17]([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 111745978-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 219841321-isobutyl-8-phenyl-1H-imidazo[4,5-c]quinolin-4-amine

Procedure

8-Bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and benzeneboronic acid were coupled according to the general procedure described in Part J of Example 1. Recrystallization from isopropanol followed by recrystallization from methanol afforded 1-isobutyl-8-phenyl-1H-imidazo[4,5-c]quinolin-4-amine as a beige solid, m.p. 203–204° C.

Workup

  1. customRecrystallization from isopropanol
  2. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-ea48b66e88164bddafa0c996a8011a44
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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