ChemicalBook CAS DataBase List Bazedoxifene

Bazedoxifene synthesis

5synthesis methods

Product Name:Bazedoxifene
CAS Number:198481-32-2
Molecular formula:C30H34N2O3
Molecular Weight:470.6

Bazedoxifene is a third generation selective estrogen receptor modulator (SERM), developed by Pfizer following the completion of their takeover of Wyeth Pharmaceuticals. In late 2013, Pfizer received approval for bazedoxifene as part of the combination drug DUAVEE in the prevention (not treatment) of postmenopausal osteoporosis. Bazedoxifene is an indole-based ER ligand that binds to both ERα (IC50 = 26 nM) and ERβ (IC50 = 99 nM).

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

Mylavarapu, Ravikumar; Kondaiah, G. C. M.; Reddy, L. Amaranth; Dubey, Manoj Kumar; Jasmine; Mukkanti, Kagga; Bandichhor, Rakeshwar. An improved synthesis of Bazedoxifene acetate. Chemistry & Biology Interface. Volume 5. Issue 2. Pages 137-150. Journal; Online Computer File. (2015).

1-[4-(2-AZEPAN-1-YL-ETHOXY)-BENZYL]-5-BENZYLOXY-2-(4-BENZYLOXY-PHENYL)-3-METHYL-1H-INDOLE

198480-21-6
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198481-32-2
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Yield:198481-32-2 100%

Reaction Conditions:

with palladium on activated charcoal;hydrogen;sodium hydroxide in ethanol;ethyl acetateSolvent;Reagent/catalyst;

Steps:

1; 6.1 The specific synthesis steps are
Add in 2000mL single-necked bottle1- (4- (2- (Acheptan-1-yl) ethoxy) benzyl) -5- (benzyloxy) -2- (4- (benzyloxy) phenyl) -3- Methyl-1H-indole175.0g, dissolved with 1400mL of ethyl acetate and ethanol mixture, then added 5ml of 1.0mol / L sodium hydroxide, and then added 52.5g of palladium on carbon,Fully reacted under hydrogen, after TLC detected the reaction,Filter to remove the catalyst palladium carbon, and then add a certain amount of L-ascorbic acid to the filtrate,Remove the solvent under reduced pressure and dry,That is, 126 g of bazedoxifene free base was obtained with a yield of 100%.

References:

Nanjing Zheng Ji Pharmaceutical Co., Ltd.;Ge Min;Gu Wen;Wang Huaiqiu;Hu Chunchen;Li Lingchao CN111004165, 2020, A Location in patent:Paragraph 0028-0031; 0044-0046

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