The development of a large scale synthesis of the glucocorticoid agonist BI 653048 BS H3PO4 is presented. A key trifluoromethyl ketone intermediate containing an N-(4-methoxyphenyl)ethyl amide was prepared by an enolization/bromine�magnesium exchange/electrophile trapping reaction. An asymmetric propargylation of trifluoromethyl ketone gave the desired diastereomer in 4:1 diastereoselectivity and 75% yield with dr = 99:1 after crystallization. The azaindole moiety was efficiently installed by a one-pot cross coupling/indolization reaction. An efficient deprotection of the 4-methoxyphenethyl group produced the desired target molecule.

Development of a large scale asymmetric synthesis of the glucocorticoid agonist BI 653048 BS H<sub>3</sub>PO<sub>4</sub>

248th National Meeting (2014)

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Development of a large scale asymmetric synthesis of the glucocorticoid agonist BI 653048 BS H3PO4

Development of a large scale asymmetric synthesis of the glucocorticoid agonist BI 653048 BS H₃PO₄