HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1778300Generated: November 3, 2026
Styrylboronic acid → (E)-N-methoxy-N-methyl-4-styrylquinoline-6-carboxamide
https://huagongshe.com/reaction/1778300
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Styrylboronic acid | HCID 5702628 | — |
| Reactant | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Reactant | Potassium phosphate, tribasic, monohydrate | HCID 22031701 | — |
| Reactant | 4-bromo-N-methoxy-N-methylquinoline-6-carboxamide | HCID 118324067 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (E)-N-methoxy-N-methyl-4-styrylquinoline-6-carboxamide | HCID 118323977 | — |
Reaction Steps
A mixture of 4-bromo-N-methoxy-N-methylquinoline-6-carboxamide (155 mg, 0.525 mmol), (E)-styrylboronic acid (155 mg, 1.05 mmol), Pd(OAc)2 (11.8 mg, 0.053 mmol), SPhos (43 mg, 0.105 mmol) and K3PO4.H2O (334 mg, 1.58 mmol) in anhydrous THF (5 mL) was heated at 35° C. overnight. The reaction was diluted with DCM and water. The organics were washed with water and concentrated. The resulting residue was purified by silica column chromatography (40-55% EtOAc/hexanes) to yield (E)-N-methoxy-N-methyl-4-styrylquinoline-6-carboxamide. (ES, m/z) 319.0 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09266835B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-2f2c80a0ab7249359877fa350a75d7bb |
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| Source note | uspto-grants-2016_02 |
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