METHODS OF PRODUCING TRICYCLIC SERD COMPOUNDS HAVING SUBSTITUTED PHENYL OR PYRIDINYL MOIETY Russian patent published in 2024 - IPC C07D209/16 C07D471/04 C07B37/02 C07B41/02 C07B43/04 

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing a compound of formula (II) or a stereoisomer or salt thereof, where each of R^1a and R^1b is independently hydrogen, halogen or unsubstituted C_1-3alkyl; each R² is independently halogen or unsubstituted C_1-3alkyl; m is 0, 1 or 2; and n is 1, 2 or 3; wherein the method includes: (a) contacting a compound of formula (III) or a stereoisomer or salt thereof with an acid selected from H₂SO₄ or ClSO₃H to form a compound of formula (IIIa) or a stereoisomer or salt thereof, (b) contacting a compound of formula (IIIa) or a stereoisomer or salt thereof with a hydroxide base to form a compound of formula (IV) or a stereoisomer or salt thereof, (c) hydrogenation of a compound of formula (IV) or a stereoisomer or salt thereof, in the presence of a catalyst, to form a compound of formula (V) or a stereoisomer or salt thereof and contacting a compound of formula (V) or a stereoisomer or salt thereof with a compound of formula (VI), thereby forming a compound of formula (II) or a stereoisomer or salt thereof. Invention also relates to methods of producing compounds of formula (I) and (1).

EFFECT: novel method of producing substituted condensed tricyclic compounds, including GDC-9545, and intermediate compounds with high output, characterized by improved process conditions and scalability.

23 cl, 6 ex