Sodium Bicarbonate → 4-[2-(4-Isopropyl-phenyl)-6-methyl-pyridin-3-yloxy]-6,7-dimethoxy-quinoline

HRID 228779

Reaction equation

I[C:2]1[C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[C:4]([CH3:23])[N:3]=1.[CH:24]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)([CH3:26])[CH3:25].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH:24]([C:27]1[CH:32]=[CH:31][C:30]([C:2]2[C:7]([O:8][C:9]3[C:18]4[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=4)[N:12]=[CH:11][CH:10]=3)=[CH:6][CH:5]=[C:4]([CH3:23])[N:3]=2)=[CH:29][CH:28]=1)([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

4-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinoline (compound 116) (84 mg), 4-isopropylphenylboronic acid (164 mg), and tetrakistriphenylphosphine palladium (12 mg) were dissolved in toluene (1 ml) to prepare a solution. A saturated aqueous sodium hydrogencarbonate solution (1 ml) was added to the solution, and the mixture was stirred at 80° C. for 3 hr. The reaction solution was filtered, the solvent was then removed by distillation under the reduced pressure, and the residue was purified by column chromatography using methanol-chloroform to give the title compound (59 mg, yield 72%).

Workup

customto prepare a solution
filtrationThe reaction solution was filtered
customthe solvent was then removed by distillation under the reduced pressure
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-54e88c2007d04f5e9b127d760a4b7175
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Linked notes

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