Synthetic Communications p. 576 - 582 (2008)
Update date:2022-08-10
Topics:
Dai, Liyan
Fan, Dongbo
Wang, Xiaozhong
Chen, Yingqi
An improved synthetic approach to tenatoprazole 1 is described. It started from 2,3,5-trimethyl-4-nitropyridine-N-oxide 2 with acetic anhydride via rearrangement and hydrolysis to give 3, Chlorination with SOCl2 yielded 2-chloromethyl-3,5-dimethyl-4-nitropyridine hydrochloride 4, then 4 condensed with 2-mercapto-5-methoxy imidazole [4,5-b]pyridine 5 to give 5-methoxy-2-[(4-nitro-3,5-dimethyl-2-pyridinyl)methylthio]imidazole[4,5-b] pyridine 6. At last the title compound 1 was produced by two methods: 6 was oxidized with MCPBA and then methoxylated with CH3ONa to give 1 and 6 was first methoxylated with CH3ONa and then oxidized with MCPBA to give 1. The overall yield is around 26% for both five-step syntheses. Copyright Taylor & Francis Group, LLC.
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