CAS: 137718-84-4; 3,4-Dibromo-2-Fluoropyridine

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36178-05-9 473596-07-5 80392-79-6

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2-fluoropyridine

📜2-氟吡啶置于溴,Lithium Diisopropyl Amide体系中,化学反应生成2-氟-3-溴吡啶,4-溴-2-氟吡啶,3,4-二溴-2-二氟吡啶
参考文献:A New Convergent Route To 1-Substituted Ellipticines
标题:A New Convergent Route To 1-Substituted Ellipticines
摘要:1-(2-Fluoro-4-Pyridyl)Ethanone Was Synthesized From 2-Fluoropyridine And Was Ortho-Lithiated After Activation As The Propylene Glycol Ketal. The Resulting 3-Lithio Derivative Was Trapped By Various Electrophiles But Reacted In Low Yield With N-Protected 3-Indolecarbaldehyde. Model Compounds 1-[[[2-(Diethylamino)Ethyl]Amino]-3-Pyridyl]Ethanol And-Ethanone Were Prepared And Selectively Condensed With Indole. 1-[[[2-(Diethylamino)-Ethyl]Amino]-3-Pyridyl]Ethanol And-Ethanone Bearing A Ketal-Protected Acetyl Moiety At The C-4 Position Have Been Obtained In High Yields Starting From The Propylene Glycol Ketal Of 1-(2-Fluoro-4-Pyridyl)Ethanone. These Reagents Could Not Be Condensed With Indole Either Due To Side Reactions Between The C-3 And C-4 Functions Or To Steric Hindrance. 1-(2-Substituted-4-Bromo-3-Pyridyl)Ethanols Were Synthesized Via A Metalation/halogen-Dance Strategy Starting From 2-Fluoropyridine. 1-(2,4-Dihalo-3-Pyridyl)-1-Chloroethane Could Be Prepared And Condensed With 1-Indolylmagnesium Iodide,Which Allowed The Construction Of The Expected 3-[1-(3-Pyridyl)Ethyl]Indole Skeleton. Functionalization Of The Pyridine C-4 Bromo Position Was Achieved By A Vinylstannane Cross-Coupling Reaction Using A Palladium(0) Catalyst. Acidic Treatment Of The Resulting 4-(1-Ethoxyethenyl)Pyridine Led To 1-Fluoroellipticine. The Whole Sequence Requires Six Steps From Indole And 2-Fluoropyridine And Allows An Attractive Overall Yield.
Doi:10.1021/jo00028A032