ChemicalBook CAS DataBase List 1-(6-METHYLPYRIDYL)-2-QUINOLIN-4-YL ETHANONE

1-(6-METHYLPYRIDYL)-2-QUINOLIN-4-YL ETHANONE synthesis

4synthesis methods

Product Name:1-(6-METHYLPYRIDYL)-2-QUINOLIN-4-YL ETHANONE
CAS Number:476472-02-3
Molecular formula:C17H14N2O
Molecular Weight:262.31

4363-93-3 Synthesis

4363-93-3
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614750-85-5 Synthesis

Phosphonic acid, P-[(6-Methyl-2-pyridinyl)(phenylaMino)Methyl]-, diphenyl ester

614750-85-5
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1-(6-METHYLPYRIDYL)-2-QUINOLIN-4-YL ETHANONE

476472-02-3
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Yield:476472-02-3 88%

Reaction Conditions:

with caesium carbonate in tetrahydrofuran;isopropyl alcohol at 20;

Steps:

1.1 Generalprocedure for the preparation of1-(6-methylpyridin-2-yl)-2-(quinolin-4-yl)ethanone (8)and 1-(6-methylpyridin-2-yl)-2-(2-phenylpyridin-4-yl)ethanone(16)

General procedure: To a stirredsolution of 7or 15(18.97 mmol) in a mixture of THF (40 mL) and i-PrOH (10 mL), diphenyl(6-methylpyridin-2-yl)(phenylamino)methylphosphonate (18.97 mmol) and Cs₂CO₃ (24.65 mmol) were added. The mixture wasstirred at room temperature for 4-16 h, and to it, 1 N HCl (75 mL) was added dropwise over a period of 5 min. The reactionmixturewas diluted with MTBE (30 mL) and stirred for1h. The aqueous layer was separated, andthe organic layer was extracted with 1 N HCl (2 × 50 mL). Thecombined aqueous layer was neutralized with 50% aqueous KOH solution (pH 7-8) and extracted with EtOAc (3× 100 mL). The EtOAc solution was dried over anhydrous Na₂SO₄,filtered, and evaporated to dryness under reduced pressure. The residue waspurified by MPLC on silica gel using EtOAc/Petroleum ether as eluent to give the titled compound 8 or 16as a light yellow solid.

References:

Jiang, Zhe;Jin, Cheng Hua;Jin, Xuejun;Li, Shanji;Li, Xiang-Yu;Li, Yan-Wei;Ma, Juan;Piao, Hu-Ri;Zhao, Li-Min [Bioorganic and medicinal chemistry letters,2019] Location in patent:supporting information