4-Propoxyphenylboronic Acid → 1-(2-methylpropyl)-9-(4-propoxyphenyl)-1H-imidazo[4,5-c]quinoline

HRID 9477Notes

Reaction equation

HRID 9477 reaction equation
Br[C:2]1[C:3]2[C:4]3[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH:13]=[N:12][C:5]=3[CH:6]=[N:7][C:8]=2[CH:9]=[CH:10][CH:11]=1.[CH2:19]([O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)[CH2:20][CH3:21]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:17][CH:16]([CH3:18])[CH2:15][N:14]1[C:4]2[C:3]3[C:2]([C:26]4[CH:27]=[CH:28][C:23]([O:22][CH2:19][CH2:20][CH3:21])=[CH:24][CH:25]=4)=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:12]=[CH:13]1

Participants

5

Reactant 2

HCID 44564904-Propoxyphenylboronic AcidHCID 219843489-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 219840881-(2-methylpropyl)-9-(4-propoxyphenyl)-1H-imidazo[4,5-c]quinolineYield 90%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

9-Bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (1.0 g, 3.4 mmol) and 4-propoxyphenylboronic acid (1.0 g, 5.5 mmol) were coupled according to Part J of Example 1. The palladium (II) acetate (2.5 mg, 0.011 mmol) was added as a 5 mg/mL solution in toluene. The work-up procedure described in Parts 125–135 was followed. The crude product was purified by HPFC (eluting with chloroform:CMA in a gradient from 100:0 to 70:30) to provide 1.1 g of 1-(2-methylpropyl)-9-(4-propoxyphenyl)-1H-imidazo[4,5-c]quinoline as a dark brown oil.

Workup

  1. customThe crude product was purified by HPFC (
  2. washeluting with chloroform

Sources & evidence

ORD record
ord-aa3baeb825a2493d835b1e3bfc26310b
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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