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• W2063972151 abstract "Lithiation of (S)-N-(1-phenylpropyl)-2-phenylquinoline-4-carboxamide with the complex n-BuLi/TMEDA (1/1 molar ratio) in THF at -60 degrees C for 5 h occurred selectively at the position 3 of the quinoline ring. This selectivity was shown by the absence of racemization of the stereogenic center and the formation of the corresponding functionalized quinolines in 59-74% yield by subsequent reaction with an electrophile at -60 degrees C for 1 h. The 3-trimethylstannyl derivative was subjected to a Stille reaction using methyl, phenyl, or thienyliodide to afford the alkyl or aryl quinolines in moderate to good yields. This methodology was successfully applied to the radiosynthesis of [11C]SB 222200 using methyl iodide labeled with carbon-11 (beta+ emitter, t1/2=20.4 min) for the in vivo study of NK-3 receptor by positron emission tomography (48-58% radiochemical yields from [11C]CH3I, decay corrected, 45 min total synthesis time)." @default.
• W2063972151 created "2016-06-24" @default.
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• W2063972151 date "2007-02-24" @default.
• W2063972151 modified "2023-09-25" @default.
• W2063972151 title "Functionalization through Lithiation of (<i>S</i>)-<i>N</i>-(1-Phenylpropyl)-2-phenylquinoline-4-carboxamide. Application to the Labeling with Carbon-11 of NK-3 Receptor Antagonist SB 222200" @default.
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• W2063972151 doi "https://doi.org/10.1021/jo062285p" @default.
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