US 12,435,034 B2
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
Jiping Fu, Danville, CA (US); Yan Lou, Dallas, TX (US); Yigang He, Newark, DE (US); Yuetao Shi, Changzhou (CN); Peng Zhou, Suzhou Industrial Park (CN); and Xingxing Li, Changzhou (CN)
Assigned to NIKANG THERAPEUTICS, INC., Wilmington, DE (US)
Filed by NiKang Therapeutics, Inc., Wilmington, DE (US)
Filed on Mar. 2, 2023, as Appl. No. 18/177,450.
Application 18/177,450 is a continuation of application No. 17/503,176, filed on Oct. 15, 2021, granted, now 11,634,382.
Claims priority of application No. PCT/CN2020/121780 (WO), filed on Oct. 19, 2020.
Prior Publication US 2023/0202970 A1, Jun. 29, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 253/30 (2006.01); C07C 29/00 (2006.01); C07C 29/143 (2006.01); C07C 45/00 (2006.01); C07C 45/27 (2006.01); C07C 45/66 (2006.01); C07C 67/307 (2006.01); C07C 67/343 (2006.01)
CPC C07C 253/30 (2013.01) [C07C 29/00 (2013.01); C07C 29/143 (2013.01); C07C 45/002 (2013.01); C07C 45/27 (2013.01); C07C 45/66 (2013.01); C07C 67/307 (2013.01); C07C 67/343 (2013.01); C07C 2602/08 (2017.05); C07C 2603/10 (2017.05)] 20 Claims
 
1. A process of preparing compound (11):

OG Complex Work Unit Chemistry
comprising reducing the keto moiety of compound (10):

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with a suitable reducing agent in a suitable organic solvent and optionally in the presence of an organic acid, wherein the reducing agent is sodium borohydride, lithium borohydride, sodium acetoxy borohydride, or sodium cyanoborohydride; and
(a) further comprising preparing compound (10):

OG Complex Work Unit Chemistry
by reacting compound (9):

OG Complex Work Unit Chemistry
with 3-fluoro-5-hydroxybenzonitrile in the presence of a base in a suitable organic solvent.