HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 228783Generated: October 27, 2026
Toluene → {4-[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl}-dimethyl-amine
https://huagongshe.com/reaction/228783
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-(Dimethylamino)phenylboronic acid | HCID 2734344 | — |
| Reactant | 4-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinoline | HCID 10093673 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | {4-[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl}-dimethyl-amine | HCID 57756439 | 80% |
Reaction Steps
Toluene (1 ml), N,N-dimethylformamide (0.5 ml) and a saturated aqueous sodium hydrogencarbonate solution (0.5 ml) were added to 4-(2-iodo-6-methyl-pyridin-3-yloxy)-6,7-dimethoxy-quinoline (compound 116) (50 mg), tetrakistriphenylphosphine palladium (28 mg), and 4-dimethylaminophenylboronic acid (196 mg) under an argon atmosphere, and the mixture was stirred at 80° C. overnight. The reaction solution was cooled to room temperature, water was then added thereto, and the mixture was extracted with chloroform. The chloroform layer was then washed with water and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform-methanol to give the title compound (39 mg, yield 80%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07560558B2 |
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| Source dataset | uspto-grants-2009_07 |
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| ORD ID | ord-cb2c83c2f70342e590e763463fb048fc |
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| Source note | uspto-grants-2009_07 |
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