Substituted imidazo [4, 5-b] pyridine compound as well as preparation method and application thereof
By reacting pyridine with phenylacetic acid with pre-introduction of N-methyl, combined with multiple steps, the problem of insufficient selectivity of unsubstituted imidazo[4,5-b]pyridine alkylation was successfully solved, and the efficient preparation of substituted imidazo[4,5-b]pyridine compounds were achieved, and good catalytic performance was shown in the copper catalytic reaction.
CN119735592APending Publication Date: 2025-04-01SHANGHAI INST OF TECH
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Patent Information
- Application Number
- CN202411768804.6
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-12-04
- Publication Date
- 2025-04-01
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Figure CN119735592A_ABST
Abstract
The invention belongs to the technical field of chemical synthesis, and relates to a substituted imidazo [4, 5-b] pyridine compound and a preparation method and application thereof.The preparation method comprises the following steps that S1, a raw material 1 # imgabs0 # is substituted with a substitution reagent to generate a compound 2 # imgabs1 # S2, in the presence of a catalyst, the compound 2 is subjected to catalytic reduction with a reducing agent to obtain a compound 3 # imgabs2 # S3, in the presence of phenylacetic acid and a condensing agent, the compound 3 # imgabs2 # S3 is subjected to condensation reaction, and the substituted imidazo [4, 5-b] pyridine compound is obtained; the method comprises the following steps: carrying out ring closure on a compound 3 to obtain a compound 4 # imgabs3 # S4, oxidizing the compound 4 by using an oxidant to obtain a compound 5 # imgabs4 # S5, chlorinating the compound 5 by using a chlorination reagent to obtain a compound 6 # imgabs5 # S6, and in the presence of a catalyst, carrying out buchwald coupling reaction on a compound 6 to obtain a target compound 7 # imgabs6 #, r is hydrogen or benzyl, and the target compound 7 # imgabs7 # imgabs8 # can be used as a catalyst ligand to show good catalytic performance in the reaction of generating C-N bonds by coupling aryl chloride and organic amine under the catalysis of copper. Compared with the prior art, the preparation method is simple and efficient, and the prepared substituted imidazo [4, 5-b] pyridine compound is high in yield.
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