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US 11,634,382 B2Granted
Process of preparing 3-fluoro-5(((1R,2aR)-3,3,4,4-tetrafluoro-1,2a-dihydroxy-2,2a,3,4-tetrahydro-1H-cyclopenta[cd]inden-7-yl)-oxy)benzonitrile
AssigneeNikang Therapeutics, Inc.
InventorsJiping Fu, Yan Lou, Yigang He, Yuetao Shi, Peng Zhou, Xingxing Li
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Abstract
Disclosed herein are processes for preparing certain intermediates useful in the synthesis of 3-fluoro-5-(((1S,2aR)-1,3,3,4,4-pentafluoro-2a-hydroxy-2,2a,3,4-tetrahydro-1H-cyclopenta[cd]inden-7-yl)oxy)benzonitrile or a pharmaceutically acceptable salt thereof.
Claims37
A process of preparing compound (11):
- comprising reducing the keto moiety of compound (10):
- with a suitable reducing agent in a suitable organic solvent and optionally in the presence of an organic acid.
A process of preparing compound (10):
- comprising reacting compound (9):
- with 3-fluoro-5-hydroxybenzonitrile in the presence of a base in a suitable organic solvent.
A process for preparing compound (9):
- comprising carrying out oxidative cleavage of the vinylidene moiety of compound (8):
- with a suitable oxidizing agent in a suitable organic or aqueous organic solvent.
A process for preparing compound (8):
- comprising performing intramolecular cyclization between the alkene and bromo groups in compound (7):
- by treating compound (7) with a palladium catalyst in the presence of a base in a suitable organic or aqueous organic solvent.
A process for preparing compound (7):
- comprising brominating compound (6):
- with a brominating agent in the presence of a deprotonating agent in a suitable organic solvent.
Dependencies are inferred from the claim text.