The synthesis of 6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-ylacetic acid (1), a selective cyclooxygenase 2 (COX-2) inhibitor, is described. The synthesis relied on a novel indole formation that involved an alkylation/1,4-addition/elimination/isomerization cascade. It was demonstrated that the entire sequence from sulfonamide 13 and bromoketone 14 to the desired indole (1) could be executed in a single pot.
Divalent tin enolates formed from stannous triflate and ketones react with carbonyl compounds under mild conditions to give the corresponding aldol products in good yields. In the case of cross-coupling with aldehydes, good to excellent erythro-selectivity was observed.
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