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Grignard Reagent Utilization Enables a Practical and Scalable Construction of 3-Substituted 5-Chloro-1,6-naphthyridin-4-one Derivatives.


ABSTRACT: A robust, practical, and scalable approach for the construction of 3-substituted 5-chloro-1,6-naphthyridin-4-one derivatives 13 via the addition of Grignard reagents to 4-amino-2-chloronicotinonitrile (15) was developed. Starting with various Grignard reagents, a wide range of 3-substituted 5-chloro-1,6-naphthyridin-4-one derivatives 13 were conveniently synthesized in moderate-to-good yields through addition-acidolysis-cyclocondensation. In addition, the robustness and applicability of this synthetic route was proven on a 100 g scale, which would enable convenient sample preparation in the preclinical development of 1,6-naphthyridin-4-one-based MET-targeting antitumor drug candidates.

SUBMITTER: Wang MS 

PROVIDER: S-EPMC7730554 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Grignard Reagent Utilization Enables a Practical and Scalable Construction of 3-Substituted 5-Chloro-1,6-naphthyridin-4-one Derivatives.

Wang Ming-Shu MS   Gong Yi Y   Yu Zhi-Cheng ZC   Tian Yan-Guang YG   Zhuo Lin-Sheng LS   Huang Wei W   She Neng-Fang NF  

Molecules (Basel, Switzerland) 20201201 23


A robust, practical, and scalable approach for the construction of 3-substituted 5-chloro-1,6-naphthyridin-4-one derivatives <b>13</b> via the addition of Grignard reagents to 4-amino-2-chloronicotinonitrile (<b>15</b>) was developed. Starting with various Grignard reagents, a wide range of 3-substituted 5-chloro-1,6-naphthyridin-4-one derivatives <b>13</b> were conveniently synthesized in moderate-to-good yields through addition-acidolysis-cyclocondensation. In addition, the robustness and appl  ...[more]

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