Sodium Bicarbonate → HCID 23078312, compound

HRID 228766Notes

Reaction equation

HRID 228766 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.[CH3:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH3:20][O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:21][CH3:22])[N:12]=[CH:11][CH:10]=[C:9]2[O:8][C:7]1[C:2]([C:29]2[CH:30]=[C:25]([CH3:24])[CH:26]=[CH:27][CH:28]=2)=[N:3][C:4]([CH3:23])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27339503-Tolylboronic acidHCID 100936734-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinoline2×

Product 1

HCID 23078312HCID 23078312, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinoline (compound 116) (84 mg), 3-methylphenylboronic acid (136 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 (72 mg, yield 94%).

Workup

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

Sources & evidence

ORD record
ord-f54772ba870e4fd689c039c33a9eefc6
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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