Thiophene-3-boronic acid → 2-ethoxymethyl-1-isobutyl-7-(thiophen-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9358

Reaction equation

HRID 9358 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][O:21][CH2:22][CH3:23])=[N:13][C:7]=3[C:8]([NH2:12])=[N:9][C:10]=2[CH:11]=1.[S:24]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25]1>>[CH2:22]([O:21][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:26]4[CH:27]=[CH:28][S:24][CH:25]=4)=[CH:11][C:10]=3[N:9]=[C:8]([NH2:12])[C:7]=2[N:13]=1)[CH3:23]

Participants

3

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 219840427-Bromo-2-ethoxymethyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 219840902-ethoxymethyl-1-isobutyl-7-(thiophen-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine

Procedure

7-Bromo-2-ethoxymethyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and thiophene-3-boronic acid were coupled according to the general procedure described in Part J of Example 1. Recrystallization from isopropanol followed by purification on silica gel (5% methanol in CH2Cl2 to 7% methanol in CH2Cl2 gradient) afforded 2-ethoxymethyl-1-isobutyl-7-(thiophen-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine as a pale yellow solid, m.p. 187–189° C.

Workup

  1. customRecrystallization from isopropanol
  2. customfollowed by purification on silica gel (5% methanol in CH2Cl2 to 7% methanol in CH2Cl2 gradient)

Sources & evidence

ORD record
ord-cf064ee4162445c1a8b080a1ce1d6cbd
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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