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198481-32-2

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198481-32-2 Usage

Uses

Bazedoxifene is an nonsteroidal selective estrogen receptor modulator (SERM). Bazedoxifene is used as an antiosteoporotic.

General Description

Bazedoxifene, 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol (Viviant), was declared to be “approvable” bythe FDA in 2007 for the prevention of postmenopausalosteoporosis. As of mid-2009, final approval in the UnitedStates is still pending. Bazedoxifene was approved inEurope in 2009 for the treatment of post–menopausalosteoporosis.

Clinical Use

Bazedoxifene is an indole-based SERM that is under investigation for the treatment and prevention of postmenopausal osteoporosis. It also is being evaluated in combination with Premarin (conjugated estrogens). Bazedoxifene displaces 17β-estradiol from estrogen receptors and has excellent binding affinity for the receptor itself. Unlike raloxifene, this agent does not cause hot flashes at the doses required to have a beneficial effect on bone. In addition, it does not cause uterine or mammary gland stimulation.

Enzyme inhibitor

This potent and selective estrogen receptor modulator, or SERM (FW = 530.65 g/mol; CAS 198481-33-3; Solubility: 00 mM in DMSO), also named 1-[[4-[2- (hexahydro-1H-azepin-1-yl) ethoxy]phenyl]methyl]-2- (4- hydroxyphenyl) -3-methyl-1H-indol-5-ol, selectivity targets the extrogen receptor ERα (IC50 = 26 nM), with weaker action against ERβ (IC50 = 99 nM), inhibiting 17β-estradiol-induced proliferation of MCF-7 cells. Bazedoxifene represents a promising new treatment for osteoporosis, one with a potential for less uterine and vasomotor effects than selective estrogen receptor modulators now used clinically.

Check Digit Verification of cas no

The CAS Registry Mumber 198481-32-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,8,4,8 and 1 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 198481-32:
(8*1)+(7*9)+(6*8)+(5*4)+(4*8)+(3*1)+(2*3)+(1*2)=182
182 % 10 = 2
So 198481-32-2 is a valid CAS Registry Number.
InChI:InChI=1/C30H34N2O3/c1-22-28-20-26(34)12-15-29(28)32(30(22)24-8-10-25(33)11-9-24)21-23-6-13-27(14-7-23)35-19-18-31-16-4-2-3-5-17-31/h6-15,20,33-34H,2-5,16-19,21H2,1H3

198481-32-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol

1.2 Other means of identification

Product number -
Other names TSE-424

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:198481-32-2 SDS

198481-32-2Synthetic route

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1-[4-(2-azepan-1-yl-ethoxy)-benzyl]-1H-indole
198480-21-6

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1-[4-(2-azepan-1-yl-ethoxy)-benzyl]-1H-indole

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; sodium hydroxide In ethanol; ethyl acetate Solvent; Reagent/catalyst;100%
With hydrogen; 2.34% Pd/C In tetrahydrofuran; ethanol for 5h;99%
With hydrogen; palladium 10% on activated carbon In methanol; water; acetone at 40℃; under 7355.72 Torr; Product distribution / selectivity;99.72%
1-[4-(2-Azepan-1-yl-ethoxy)-benzyl]-5-methoxy-2-(4-methoxy-phenyl)-3-methyl-1H-indole

1-[4-(2-Azepan-1-yl-ethoxy)-benzyl]-5-methoxy-2-(4-methoxy-phenyl)-3-methyl-1H-indole

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With trimethylsilyl iodide In chloroform at 20℃; for 5h;95%
With hydrogen iodide36.3 g
1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride
223251-25-0

1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride

4-(5-acetoxy-3-methyl-1H-indol-2-yl)phenyl acetate
91444-55-2

4-(5-acetoxy-3-methyl-1H-indol-2-yl)phenyl acetate

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
Stage #1: 4-(5-acetoxy-3-methyl-1H-indol-2-yl)phenyl acetate With sodium hydride In N,N-dimethyl-formamide at 0 - 5℃; for 2h; Inert atmosphere;
Stage #2: 1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 15h;
Stage #3: With sodium hydroxide In N,N-dimethyl-formamide at 25℃; for 15h; Solvent; Temperature; Reagent/catalyst;
89%
1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-5-(tert-butoxy)-2-(4-(tert-butoxy)phenyl)-3-methyl-1H-indole

1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-5-(tert-butoxy)-2-(4-(tert-butoxy)phenyl)-3-methyl-1H-indole

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With hydrogen bromide; acetic acid at 20℃; for 0.5h;87%
1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-2-(4-(benzoyloxy)phenyl)-3-methyl-1H-indol-5-yl benzoate

1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-2-(4-(benzoyloxy)phenyl)-3-methyl-1H-indol-5-yl benzoate

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With triethylamine In methanol; water for 5h; Reflux;86%
1-[4-(2-azepan-1-yl-ethoxy)benzyl]-5-benzyloxy-2-(4-benzyloxyphenyl)-3-methyl-1H-indole

1-[4-(2-azepan-1-yl-ethoxy)benzyl]-5-benzyloxy-2-(4-benzyloxyphenyl)-3-methyl-1H-indole

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With ammonium formate; 10 wt% Pd(OH)2 on carbon In acetone85%
4-(5-acetoxy-1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-3-methyl-1H-indol-2-yl)phenyl acetate

4-(5-acetoxy-1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-3-methyl-1H-indol-2-yl)phenyl acetate

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With ammonia In methanol; water at 20℃; for 3h;85%
1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-3-methyl-2-(4-(pivaloyloxy)phenyl)-1Hindol-5-yl pivalate

1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-3-methyl-2-(4-(pivaloyloxy)phenyl)-1Hindol-5-yl pivalate

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With methanol; potassium carbonate at 45℃; for 3h;83%
1-(2-{4-[5-Hydroxy-2-(4-hydroxy-phenyl)-3-methyl-indol-1-ylmethyl]-phenoxy}-ethyl)-azepane-2,7-dione
1251936-45-4

1-(2-{4-[5-Hydroxy-2-(4-hydroxy-phenyl)-3-methyl-indol-1-ylmethyl]-phenoxy}-ethyl)-azepane-2,7-dione

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 5 - 10℃; for 4h;80.7%
hexamethylene imine
111-49-9

hexamethylene imine

2-(4-((5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)ethyl 4-methylbenzenesulfonate
1343413-19-3

2-(4-((5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)ethyl 4-methylbenzenesulfonate

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
In toluene at 70 - 75℃; for 12h;80%
ethyl 2-((1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-2-(4-(2-ethoxy-2-oxoethoxy)phenyl)-3-methyl-1H-indol-5-yl)oxy)acetate

ethyl 2-((1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-2-(4-(2-ethoxy-2-oxoethoxy)phenyl)-3-methyl-1H-indol-5-yl)oxy)acetate

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 20℃; for 3h;79%
1-[4-(2-azepan-1-yl-ethoxy)-benzyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indol-5-ol hydrochloride

1-[4-(2-azepan-1-yl-ethoxy)-benzyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indol-5-ol hydrochloride

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With triethylamine In dichloromethane; water pH=9.5 - 10.5; Product distribution / selectivity;73.27%
1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride
223251-25-0

1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride

2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol
91444-54-1

2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
Stage #1: 1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride; 2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;
Stage #2: 1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride In N,N-dimethyl-formamide at 0 - 5℃; for 3.91h;
70.18%
1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-5-(2-ethoxyethoxy)-2-(4-(2-ethoxyethoxy)phenyl)-3-methyl-1H-indole

1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-5-(2-ethoxyethoxy)-2-(4-(2-ethoxyethoxy)phenyl)-3-methyl-1H-indole

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With boron tribromide In methanol for 5h; Reflux;69%
1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-5-(cyclopentyloxy)-2-(4-(cyclopentyloxy)phenyl)-3-methyl-1H-indole

1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-5-(cyclopentyloxy)-2-(4-(cyclopentyloxy)phenyl)-3-methyl-1H-indole

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With hydrogen bromide; acetic acid In methanol at 50℃; for 2h;61%
hexanedial
1072-21-5

hexanedial

1-[4-(2-Amino-ethoxy)-benzyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indol-5-ol
1251936-44-3

1-[4-(2-Amino-ethoxy)-benzyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indol-5-ol

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
10 wt% Pd(OH)2 on carbon at 45 - 50℃; under 3677.86 - 5884.58 Torr;45%
1-(4-(2(azepan-1-yl)ethoxy)benzyl)-5-((2-methoxyethoxy)methoxy)-2-(4-((2-methoxyethoxy)methoxy)phenyl)-3-methyl-1H-indole

1-(4-(2(azepan-1-yl)ethoxy)benzyl)-5-((2-methoxyethoxy)methoxy)-2-(4-((2-methoxyethoxy)methoxy)phenyl)-3-methyl-1H-indole

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With acetyl chloride In methanol at 0 - 2℃; for 3h;42%
1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-5-((4-methoxybenzyl)oxy)-2-(4-((4-methoxybenzyl)oxy)phenyl)-3-methyl-1H-indole

1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-5-((4-methoxybenzyl)oxy)-2-(4-((4-methoxybenzyl)oxy)phenyl)-3-methyl-1H-indole

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 20h;15%
(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: K2CO3
2.1: SOCl2 / tetrahydrofuran
3.1: sodium hydride / dimethylformamide / 0.33 h / 0 °C
3.2: 59 percent / dimethylformamide / 18 h / 20 °C
4.1: 78 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
5.1: 87 percent / CBr4; Ph3P / tetrahydrofuran / 3 h / 20 °C
6.1: tetrahydrofuran
7.1: H2 / Pd/C / ethanol; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / Reflux
2.1: hydrogenchloride / dichloromethane / 25 - 35 °C / Inert atmosphere
3.1: sodium hydride / N,N-dimethyl-formamide; toluene / -5 - -1 °C
3.2: 5 °C
4.1: hydrogen / palladium 10% on activated carbon / water; acetone; methanol / 40 °C / 7355.72 Torr
View Scheme
Multi-step reaction with 7 steps
1.1: potassium carbonate / acetonitrile / 60 °C
2.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 0.75 h / 0 °C / Inert atmosphere
3.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C
3.2: 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C
5.1: carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 20 °C
6.1: tetrahydrofuran / Reflux
7.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 20 °C
View Scheme
1-<4-(benzyloxy)phenyl>-2-bromo-1-propanone
35081-45-9

1-<4-(benzyloxy)phenyl>-2-bromo-1-propanone

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 51 percent / Et3N / dimethylformamide / Heating
2.1: sodium hydride / dimethylformamide / 0.33 h / 0 °C
2.2: 59 percent / dimethylformamide / 18 h / 20 °C
3.1: 78 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
4.1: 87 percent / CBr4; Ph3P / tetrahydrofuran / 3 h / 20 °C
5.1: tetrahydrofuran
6.1: H2 / Pd/C / ethanol; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / N,N-dimethyl-formamide / 100 - 125 °C
2.1: sodium hydride / N,N-dimethyl-formamide; toluene / -5 - -1 °C
2.2: 5 °C
3.1: hydrogen / palladium 10% on activated carbon / water; acetone; methanol / 40 °C / 7355.72 Torr
View Scheme
Multi-step reaction with 6 steps
1.1: triethylamine / N,N-dimethyl-formamide / 4 h / 120 - 150 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C
2.2: 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C
4.1: carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 20 °C
5.1: tetrahydrofuran / Reflux
6.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / N,N-dimethyl-formamide / 4 h / 115 °C
2: sodium hydride / N,N-dimethyl-formamide / 10 h / 20 °C
3: boron trifluoride diethyl etherate / dichloromethane; ethanethiol / 4 h / 0 - 25 °C
View Scheme
4-benzyloxyaniline hydrochloride
51388-20-6

4-benzyloxyaniline hydrochloride

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 51 percent / Et3N / dimethylformamide / Heating
2.1: sodium hydride / dimethylformamide / 0.33 h / 0 °C
2.2: 59 percent / dimethylformamide / 18 h / 20 °C
3.1: 78 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
4.1: 87 percent / CBr4; Ph3P / tetrahydrofuran / 3 h / 20 °C
5.1: tetrahydrofuran
6.1: H2 / Pd/C / ethanol; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / N,N-dimethyl-formamide / 100 - 125 °C
2.1: sodium hydride / N,N-dimethyl-formamide; toluene / -5 - -1 °C
2.2: 5 °C
3.1: hydrogen / palladium 10% on activated carbon / water; acetone; methanol / 40 °C / 7355.72 Torr
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / N,N-dimethyl-formamide / 4 h / 115 °C
2: sodium hydride / N,N-dimethyl-formamide / 10 h / 20 °C
3: boron trifluoride diethyl etherate / dichloromethane; ethanethiol / 4 h / 0 - 25 °C
View Scheme
ethyl [p-(chloromethyl)phenoxy]acetate
80494-75-3

ethyl [p-(chloromethyl)phenoxy]acetate

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydride / dimethylformamide / 0.33 h / 0 °C
1.2: 59 percent / dimethylformamide / 18 h / 20 °C
2.1: 78 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
3.1: 87 percent / CBr4; Ph3P / tetrahydrofuran / 3 h / 20 °C
4.1: tetrahydrofuran
5.1: H2 / Pd/C / ethanol; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C
3.1: carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 20 °C
4.1: tetrahydrofuran / Reflux
5.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 20 °C
View Scheme
ethyl 2-(4-hydroxymethylphenoxy)acetate
103258-64-6

ethyl 2-(4-hydroxymethylphenoxy)acetate

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: SOCl2 / tetrahydrofuran
2.1: sodium hydride / dimethylformamide / 0.33 h / 0 °C
2.2: 59 percent / dimethylformamide / 18 h / 20 °C
3.1: 78 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
4.1: 87 percent / CBr4; Ph3P / tetrahydrofuran / 3 h / 20 °C
5.1: tetrahydrofuran
6.1: H2 / Pd/C / ethanol; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 0.75 h / 0 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C
2.2: 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C
4.1: carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 20 °C
5.1: tetrahydrofuran / Reflux
6.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 20 °C
View Scheme
5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydride / dimethylformamide / 0.33 h / 0 °C
1.2: 59 percent / dimethylformamide / 18 h / 20 °C
2.1: 78 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
3.1: 87 percent / CBr4; Ph3P / tetrahydrofuran / 3 h / 20 °C
4.1: tetrahydrofuran
5.1: H2 / Pd/C / ethanol; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide; toluene / -5 - -1 °C
1.2: 5 °C
2.1: hydrogen / palladium 10% on activated carbon / water; acetone; methanol / 40 °C / 7355.72 Torr
View Scheme
Multi-step reaction with 5 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C
3.1: carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 20 °C
4.1: tetrahydrofuran / Reflux
5.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 20 °C
View Scheme
2-(4-((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)ethanol
198479-95-7

2-(4-((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)ethanol

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 87 percent / CBr4; Ph3P / tetrahydrofuran / 3 h / 20 °C
2: tetrahydrofuran
3: H2 / Pd/C / ethanol; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 20 °C
2: tetrahydrofuran / Reflux
3: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 20 °C
View Scheme
5-benzyloxy-2-(4-benzyloxy-phenyl)-1-[4-(2-bromo-ethoxy)-benzyl]-3-methyl-1H-indole
198480-07-8

5-benzyloxy-2-(4-benzyloxy-phenyl)-1-[4-(2-bromo-ethoxy)-benzyl]-3-methyl-1H-indole

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran
2: H2 / Pd/C / ethanol; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: tetrahydrofuran / Reflux
2: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 20 °C
View Scheme
{4-[5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-indol-1-ylmethyl]-phenoxy}-acetic acid ethyl ester
198479-82-2

{4-[5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-indol-1-ylmethyl]-phenoxy}-acetic acid ethyl ester

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 78 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
2: 87 percent / CBr4; Ph3P / tetrahydrofuran / 3 h / 20 °C
3: tetrahydrofuran
4: H2 / Pd/C / ethanol; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C
2: carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 20 °C
3: tetrahydrofuran / Reflux
4: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 20 °C
View Scheme
C30H36N2O9P2
1049816-47-8

C30H36N2O9P2

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
With water; alkaline phosphatase pH=7.4; Conversion of starting material; Tris buffer; Enzymatic reaction;
[4-(2-hexamethyleneimino-1-yl-ethoxy)-phenyl]-methanol
223251-16-9

[4-(2-hexamethyleneimino-1-yl-ethoxy)-phenyl]-methanol

bazedoxifene
198481-32-2

bazedoxifene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride / dichloromethane / 25 - 35 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide; toluene / -5 - -1 °C
2.2: 5 °C
3.1: hydrogen / palladium 10% on activated carbon / water; acetone; methanol / 40 °C / 7355.72 Torr
View Scheme
acetic acid
64-19-7

acetic acid

bazedoxifene
198481-32-2

bazedoxifene

bazedoxifene acetate

bazedoxifene acetate

Conditions
ConditionsYield
for 6h; Heating;98.5%
In ethanol; ethyl acetate at 20 - 30℃;95.5%
In acetone at 20 - 55℃;95%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

bazedoxifene
198481-32-2

bazedoxifene

C42H62N2O3Si2

C42H62N2O3Si2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;93.48%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

bazedoxifene
198481-32-2

bazedoxifene

C36H50N2O3Si2

C36H50N2O3Si2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;90.3%
bazedoxifene
198481-32-2

bazedoxifene

1-[4-(2-azepan-1-yl-ethoxy)-benzyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indol-5-ol hydrochloride

1-[4-(2-azepan-1-yl-ethoxy)-benzyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indol-5-ol hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol Product distribution / selectivity;87.79%
With hydrogenchloride In methanol; water
L-Lactic acid
79-33-4

L-Lactic acid

bazedoxifene
198481-32-2

bazedoxifene

bazedoxifene L-lactate
1354966-34-9

bazedoxifene L-lactate

Conditions
ConditionsYield
Stage #1: L-Lactic acid In ethanol at 60℃; for 0.25h;
Stage #2: bazedoxifene In ethanol at 60℃; for 0.333333h; Solvent;
66.4%
propionic acid
802294-64-0

propionic acid

bazedoxifene
198481-32-2

bazedoxifene

1-[4-(2-azepan-1-yl-ethoxy)benzyl]-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol propionate
1266685-12-4

1-[4-(2-azepan-1-yl-ethoxy)benzyl]-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol propionate

Conditions
ConditionsYield
In acetone60.23%
formic acid
64-18-6

formic acid

bazedoxifene
198481-32-2

bazedoxifene

1-[4-(2-azepan-1-ylethoxy)benzyl]-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol formic acid salt

1-[4-(2-azepan-1-ylethoxy)benzyl]-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol formic acid salt

Conditions
ConditionsYield
In ethyl acetate at 77℃;50%

198481-32-2Relevant articles and documents

Preparation method of bazedoxifene acetate crystal form A

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Paragraph 0028-0031; 0044-0046, (2020/04/22)

The invention discloses a preparation method of a bazedoxifene acetate crystal form A. The method comprises the following steps: taking 1-(4-(2-(azepine-1-yl) ethoxy) benzyl)-5-(benzyloxy)-2-(4-(benzyloxy) phenyl)-3-methyl-1H-indole as a raw material; preparing bazedoxifene acetate free alkali, preparing a bazedoxifene acetate crude product, preparing a bazedoxifene acetate crystal form B, preparing a bazedoxifene acetate crystal form C and preparing the bazedoxifene acetate crystal form A. A mixed solvent is adopted in the hydrogenation process of the method; the rate and the activity of thepalladium-carbon reduction reaction are improved; an antioxidant is added, so that the stability of the bazedoxifene free alkali is improved, the conversion from the crystal form B to the crystal formC is increased in the middle, key parameters for converting the crystal form C into the crystal form A are found, the purity of the crystal form A in the next step is greatly improved, and the production cost for producing the bazedoxifene acetate crystal form A is effectively reduced.

METHODS OF PREPARINGBAZEDOXIFENE BY NEW INTERMEDIATES

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, (2019/12/25)

The present invention relates to a method for manufacturing novel bazedoxifene or a pharmaceutically acceptable salt thereof. A manufacturing method according to the present invention can provide high purity and high yield of bazedoxifene, and is economical in terms of time and cost and eco-friendly due to a relatively simple manufacturing process, thereby being able to be usefully applied to mass production.COPYRIGHT KIPO 2020

METHODS OF PREPARING BAZOEDOXIFENE

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, (2018/10/16)

The present invention relates to novel bazedoxifene or to a method for producing a pharmaceutically acceptable salt thereof. The production method according to the present invention can provide the bazedoxifene with high purity and high yield, and is economical and environmentally friendly in terms of time and cost due to a relatively simple manufacturing process to be usefully applied to mass production.COPYRIGHT KIPO 2018

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