Phenylboronic Acid → 2-ethyl-1-isobutyl-8-phenyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9372Notes

Reaction equation

HRID 9372 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]([NH2:12])[C:6]3[N:13]=[C:14]([CH2:20][CH3:21])[N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:5]=3[C:4]=2[CH:3]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:20]([C:14]1[N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:5]2[C:4]3[CH:3]=[C:2]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:11]=[CH:10][C:9]=3[N:8]=[C:7]([NH2:12])[C:6]=2[N:13]=1)[CH3:21]

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 219843008-Bromo-2-ethyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 219840482-ethyl-1-isobutyl-8-phenyl-1H-imidazo[4,5-c]quinolin-4-amine

Procedure

8-Bromo-2-ethyl-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. Chromatography on silica gel (5%–7% methanol in CH2Cl2 gradient) afforded 2-ethyl-1-isobutyl-8-phenyl-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, m.p. 233–235° C.

Sources & evidence

ORD record
ord-81344968fab24210b3c08586347dafa4
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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