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198479-63-9

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198479-63-9 Usage

Uses

3-Methyl-5-(phenylmethoxy)-2-[4-(phenylmethoxy)phenyl]-1H-indole is an intermediate of Bazedoxifene acetate (B129250).

Check Digit Verification of cas no

The CAS Registry Mumber 198479-63-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,8,4,7 and 9 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 198479-63:
(8*1)+(7*9)+(6*8)+(5*4)+(4*7)+(3*9)+(2*6)+(1*3)=209
209 % 10 = 9
So 198479-63-9 is a valid CAS Registry Number.
InChI:InChI=1/C29H25NO2/c1-21-27-18-26(32-20-23-10-6-3-7-11-23)16-17-28(27)30-29(21)24-12-14-25(15-13-24)31-19-22-8-4-2-5-9-22/h2-18,30H,19-20H2,1H3

198479-63-9SDS

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 3-methyl-5-phenylmethoxy-2-(4-phenylmethoxyphenyl)-1H-indole

1.2 Other means of identification

Product number -
Other names Bazedoxifene intermediate I

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:198479-63-9 SDS

198479-63-9Synthetic route

1-<4-(benzyloxy)phenyl>-2-bromo-1-propanone
35081-45-9

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

4-benzyloxyaniline hydrochloride
51388-20-6

4-benzyloxyaniline hydrochloride

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 115℃; for 4h; Temperature; Reagent/catalyst;94.6%
Stage #1: 1-<4-(benzyloxy)phenyl>-2-bromo-1-propanone; 4-benzyloxyaniline hydrochloride With triethylamine In butan-1-ol at 118℃; for 3h; Bischler-Moehlau Indole Synthesis;
Stage #2: With hydrogenchloride In water; butan-1-ol at 118℃; for 7h; Temperature; Reagent/catalyst; Bischler-Moehlau Indole Synthesis;
90.5%
With triethylamine In N,N-dimethyl-formamide at 120 - 150℃; for 4h; Bischler indole synthesis; Inert atmosphere;84.9%
4-benzyloxypropiophenone
4495-66-3

4-benzyloxypropiophenone

4-benzyloxyphenylhydrazine hydrochloride
52068-30-1

4-benzyloxyphenylhydrazine hydrochloride

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
With acetic acid In ethanol at 75 - 80℃; Product distribution / selectivity;94%
acetic acid In ethanol at 75 - 80℃; for 12h; Product distribution / selectivity;94%
With hydrogenchloride In ethanol for 2h; Reflux;84%
C33H27N3O2

C33H27N3O2

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
With sodium ethanolate In ethanol; dimethyl sulfoxide at 100℃; for 20h;85%
With sodium ethanolate In dimethyl sulfoxide at 130℃;72%
1-(4-benzyloxyphenyl)-2-morpholin-4-yl-propan-1-one

1-(4-benzyloxyphenyl)-2-morpholin-4-yl-propan-1-one

4-benzyloxyaniline hydrochloride
51388-20-6

4-benzyloxyaniline hydrochloride

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
In chlorobenzene at 125 - 130℃; for 8h; Large scale;83.5%
1-(4-benzyloxyphenyl)-2-(4-benzyloxy-phenylamino)-1-propanone
1048697-94-4

1-(4-benzyloxyphenyl)-2-(4-benzyloxy-phenylamino)-1-propanone

4-benzyloxyaniline hydrochloride
51388-20-6

4-benzyloxyaniline hydrochloride

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
In isopropyl alcohol at 110 - 115℃; for 5h; Product distribution / selectivity;82%
In ethanol at 110 - 115℃; for 5h; Product distribution / selectivity;79%
1-(4-benzyloxyphenyl)-2-(4-benzyloxy-phenylamino)-1-propanone
1048697-94-4

1-(4-benzyloxyphenyl)-2-(4-benzyloxy-phenylamino)-1-propanone

p-benzyloxyaniline
6373-46-2

p-benzyloxyaniline

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
In 2-ethoxy-ethanol for 6h; Reflux;80.5%
4’-benzyloxy-2-bromophenyl propiophenone

4’-benzyloxy-2-bromophenyl propiophenone

4-benzyloxyaniline hydrochloride
51388-20-6

4-benzyloxyaniline hydrochloride

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 2.5h; Reflux;65%
4’-benzyloxy-2-bromophenyl propiophenone

4’-benzyloxy-2-bromophenyl propiophenone

p-benzyloxyaniline
6373-46-2

p-benzyloxyaniline

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
In dichloromethane; ethyl acetate; N,N-dimethyl-formamide33%
In dichloromethane; ethyl acetate; N,N-dimethyl-formamide33%
In dichloromethane; ethyl acetate; N,N-dimethyl-formamide33%
4-benzyloxy-2-bromophenylpropiophenone

4-benzyloxy-2-bromophenylpropiophenone

p-benzyloxyaniline
6373-46-2

p-benzyloxyaniline

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
In dichloromethane; ethyl acetate; N,N-dimethyl-formamide33%
p-benzyloxyaniline
6373-46-2

p-benzyloxyaniline

4-benzyloxypropiophenone
4495-66-3

4-benzyloxypropiophenone

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 125℃; for 6h;23%
4-benzyloxypropiophenone
4495-66-3

4-benzyloxypropiophenone

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bromine / acetic acid / 3 h / 0 - 20 °C
2: triethylamine / N,N-dimethyl-formamide / 4 h / 120 - 150 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: bromine / 1,4-dioxane; methanol / 1 h / 20 °C
2: triethylamine / ethanol / 5 h / 20 °C
3: 2-ethoxy-ethanol / 6 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: aluminum (III) chloride; bromine / toluene; methanol / 40 - 45 °C / Large scale
2: toluene / 2 h / 110 °C / Reflux; Large scale
3: chlorobenzene / 8 h / 125 - 130 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1: bromine; acetic acid / 1 h / 0 °C
2: triethylamine / N,N-dimethyl-formamide / 5 h / 120 - 150 °C
View Scheme
benzyl bromide
100-39-0

benzyl bromide

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 60 °C
2: bromine / acetic acid / 3 h / 0 - 20 °C
3: triethylamine / N,N-dimethyl-formamide / 4 h / 120 - 150 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / 60 °C
2: triethylamine / N,N-dimethyl-formamide / 6 h / 125 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 18 h / Reflux
2: bromine; acetic acid / 1 h / 0 °C
3: triethylamine / N,N-dimethyl-formamide / 5 h / 120 - 150 °C
View Scheme
4-hydroxypropiophenone
70-70-2

4-hydroxypropiophenone

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 60 °C
2: bromine / acetic acid / 3 h / 0 - 20 °C
3: triethylamine / N,N-dimethyl-formamide / 4 h / 120 - 150 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / acetonitrile / 16 h / 20 °C / Inert atmosphere
2: hydrogenchloride / ethanol / 2 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate / acetone / 24 h / Reflux
2: bromine / 1,4-dioxane; methanol / 1 h / 20 °C
3: triethylamine / ethanol / 5 h / 20 °C
4: 2-ethoxy-ethanol / 6 h / Reflux
View Scheme
1-<4-(benzyloxy)phenyl>-2-bromo-1-propanone
35081-45-9

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

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / ethanol / 5 h / 20 °C
2: 2-ethoxy-ethanol / 6 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: toluene / 2 h / 110 °C / Reflux; Large scale
2: chlorobenzene / 8 h / 125 - 130 °C / Large scale
View Scheme
4-nitro-phenol
100-02-7

4-nitro-phenol

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 24 h / Reflux
2: tin(ll) chloride / ethanol / 24 h / 45 °C / Inert atmosphere
3: 2-ethoxy-ethanol / 6 h / Reflux
View Scheme
benzyl chloride
100-44-7

benzyl chloride

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 24 h / Reflux
2: tin(ll) chloride / ethanol / 24 h / 45 °C / Inert atmosphere
3: 2-ethoxy-ethanol / 6 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate / acetone / 24 h / Reflux
2: bromine / 1,4-dioxane; methanol / 1 h / 20 °C
3: triethylamine / ethanol / 5 h / 20 °C
4: 2-ethoxy-ethanol / 6 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: tetrabutylammomium bromide / toluene; water / 90 °C / Reflux; Large scale
1.2: Reflux; Large scale
2.1: aluminum (III) chloride; bromine / toluene; methanol / 40 - 45 °C / Large scale
3.1: toluene / 2 h / 110 °C / Reflux; Large scale
4.1: chlorobenzene / 8 h / 125 - 130 °C / Large scale
View Scheme
benzyl 4-nitrophenyl ether
1145-76-2

benzyl 4-nitrophenyl ether

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tin(ll) chloride / ethanol / 24 h / 45 °C / Inert atmosphere
2: 2-ethoxy-ethanol / 6 h / Reflux
View Scheme
1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride
223251-25-0

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

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

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

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 10h; Time; Reagent/catalyst;93.7%
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydroxide In water; dimethyl sulfoxide at 20℃; for 1h; Large scale;
Stage #2: 1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 1h; Solvent; Time; Large scale;
91.8%
With sodium hydride In N,N-dimethyl acetamide at 0 - 10℃; for 0.5h; Large scale;82.6%
(4-chloromethylphenoxy)acetonitrile
112772-83-5

(4-chloromethylphenoxy)acetonitrile

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

{4-[5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-indol-1-ylmethyl]-phenoxy}-acetonitrile
1251936-40-9

{4-[5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-indol-1-ylmethyl]-phenoxy}-acetonitrile

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium amide In N,N-dimethyl-formamide at 10 - 15℃; for 0.25h;
Stage #2: 4-chloromethyl phenoxy acetonitrile In N,N-dimethyl-formamide at 10 - 15℃;
80%
5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

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

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

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol at 20℃;78.3%
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere
1.2: 2.5 h / 0 °C / Inert atmosphere; Reflux
2.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; ethyl acetate / 0.5 h
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere
1.2: 2.5 h / 0 °C / Inert atmosphere; Reflux
2.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; ethyl acetate / 0.5 h
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere
1.2: 2.5 h / 0 °C / Inert atmosphere; Reflux
2.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; ethyl acetate / 0.5 h
View Scheme
tert-butyl (4-(4-(bromomethyl)phenoxy)butyl)carbamate

tert-butyl (4-(4-(bromomethyl)phenoxy)butyl)carbamate

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

tert-butyl (4-(4-((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)butyl)carbamate

tert-butyl (4-(4-((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)butyl)carbamate

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: tert-butyl (4-(4-(bromomethyl)phenoxy)butyl)carbamate In N,N-dimethyl-formamide at 0 - 20℃; for 12h;
73%
4-(benzyloxy)benzyl bromide
5544-60-5

4-(benzyloxy)benzyl bromide

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

A

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

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

B

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

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

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 4-(benzyloxy)benzyl bromide In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere; Reflux;
A 68%
B 30%
4-Fluorobenzyl bromide
459-46-1

4-Fluorobenzyl bromide

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

A

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

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

B

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

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

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 4-Fluorobenzyl bromide In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere; Reflux;
A 23%
B 68%
1-[(S)-2-(4-Chloromethyl-phenoxy)-1-methyl-ethyl]-pyrrolidine
869006-43-9

1-[(S)-2-(4-Chloromethyl-phenoxy)-1-methyl-ethyl]-pyrrolidine

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1-[4-(2-pyrrolidin-1-yl-propoxy)-benzyl]-1H-indole
869006-49-5

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

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide67%
(R)-1-[2-(4-Chloromethyl-phenoxy)-ethyl]-3-methyl-pyrrolidine
869006-41-7

(R)-1-[2-(4-Chloromethyl-phenoxy)-ethyl]-3-methyl-pyrrolidine

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1-{4-[2-(3-methyl-pyrrolidin-1-yl)-ethoxy]-benzyl}-1H-indole
869006-47-3

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

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide67%
1 ,6-dibromohexane
629-03-8

1 ,6-dibromohexane

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

A

1,6-bis(5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)hexane

1,6-bis(5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)hexane

B

C35H36BrNO2

C35H36BrNO2

C

C35H36BrNO2

C35H36BrNO2

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 1 ,6-dibromohexane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
A 26%
B 66%
C 12%
1-(bromomethyl)-4-(triphenylmethoxy)benzene
1215269-88-7

1-(bromomethyl)-4-(triphenylmethoxy)benzene

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

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

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

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h;
Stage #2: 1-(bromomethyl)-4-(triphenylmethoxy)benzene In N,N-dimethyl-formamide at 0℃; for 2h;
66%
1,5-dibromo-pentane
111-24-0

1,5-dibromo-pentane

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

A

1,5-bis(5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)pentane

1,5-bis(5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)pentane

B

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

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

C

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

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

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 1,5-dibromo-pentane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
A 22%
B 9%
C 65%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

A

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

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

B

6-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-(4-bromobutyl)-3-methyl-3H-indole

6-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-(4-bromobutyl)-3-methyl-3H-indole

C

1,4-bis(5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)butane

1,4-bis(5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)butane

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 1,4-dibromo-butane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
A 63%
B 17%
C 20%
1,4-bis(bromomethyl)benzene
623-24-5

1,4-bis(bromomethyl)benzene

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

A

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

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

B

1,4-bis((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)benzene

1,4-bis((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)benzene

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 1,4-bis(bromomethyl)benzene In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
A 22%
B 63%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

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

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

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide for 0.666667h;
Stage #2: 1,4-dibromo-butane With N,N-dimethyl-formamide at 20℃; for 2.5h;
60.6%
2-(4-bromomethylphenoxy)ethyl 4-methylbenzenesulfonate
1343413-04-6

2-(4-bromomethylphenoxy)ethyl 4-methylbenzenesulfonate

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

A

C45H41NO6S

C45H41NO6S

B

2-(4-{[5-(benzyloxy)-2-[4-(benzyloxy)phenyl]-3-methyl-1H-indol-1-yl]methyl}phenoxy)ethyl 4-methylbenzene-1-sulfonate
1343413-11-5

2-(4-{[5-(benzyloxy)-2-[4-(benzyloxy)phenyl]-3-methyl-1H-indol-1-yl]methyl}phenoxy)ethyl 4-methylbenzene-1-sulfonate

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide at -10 - -5℃; for 0.5h;
Stage #2: 2-(4-bromomethylphenoxy)ethyl 4-methylbenzenesulfonate In N,N-dimethyl-formamide at -5 - 0℃; for 3h;
Stage #3: With acetic acid In N,N-dimethyl-formamide
A n/a
B 60%
1,8-dibromooctane
4549-32-0

1,8-dibromooctane

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

A

5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-1-(8-bromooctyl)-3-methyl-1H-indole

5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-1-(8-bromooctyl)-3-methyl-1H-indole

B

1,8-bis(5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)octane

1,8-bis(5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)octane

C

6-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-(8-bromooctyl)-3-methyl-3H-indole

6-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-(8-bromooctyl)-3-methyl-3H-indole

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 1,8-dibromooctane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
A 60%
B 22%
C 13%
ethyl [p-(chloromethyl)phenoxy]acetate
80494-75-3

ethyl [p-(chloromethyl)phenoxy]acetate

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

{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

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h;
Stage #2: ethyl [p-(chloromethyl)phenoxy]acetate In N,N-dimethyl-formamide at 20℃; for 18h; Further stages.;
59%
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h;
Stage #2: ethyl [p-(chloromethyl)phenoxy]acetate In N,N-dimethyl-formamide at 20℃;
29.7%
1,12-dibromododecane
3344-70-5

1,12-dibromododecane

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

A

6-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-(12-bromododecyl)-3-methyl-3H-indole

6-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-(12-bromododecyl)-3-methyl-3H-indole

B

5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-1-(12-bromododecyl)-3-methyl-1H-indole

5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-1-(12-bromododecyl)-3-methyl-1H-indole

C

1,12-bis(5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)dodecane

1,12-bis(5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)dodecane

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 1,12-dibromododecane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
A 11%
B 59%
C 30%
3,4,5-trimethoxybenzyl bromide
21852-50-6

3,4,5-trimethoxybenzyl bromide

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

A

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

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

B

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

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

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 3,4,5-trimethoxybenzyl bromide In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere; Reflux;
A 17%
B 51%
3-phenoxypropyl bromide
588-63-6

3-phenoxypropyl bromide

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

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

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

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: 3-phenoxypropyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;
46.7%
bromoethyl-2-benzyl ether
1462-37-9

bromoethyl-2-benzyl ether

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

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

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

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: bromoethyl-2-benzyl ether In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere; Reflux;
43%
phenoxyethyl bromide
589-10-6

phenoxyethyl bromide

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole
198479-63-9

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

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

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

Conditions
ConditionsYield
Stage #1: 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: phenoxyethyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;
41.2%

198479-63-9Relevant articles and documents

Cobalt-catalyzed intramolecular decarbonylative coupling of acylindoles and diarylketones through the cleavage of C-C bonds

Lu, Hong,Wei, Hao,Xu, Wen-Hua,Yu, Tian-Yang

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We report here cobalt-N-heterocyclic carbene catalytic systems for the intramolecular decarbonylative coupling through the chelation-assisted C-C bond cleavage of acylindoles and diarylketones. The reaction tolerates a wide range of functional groups such as alkyl, aryl, and heteroaryl groups, giving the decarbonylative products in moderate to excellent yields. This transformation involves the cleavage of two C-C bonds and formation of a new C-C bond without the use of noble metals, thus reinforcing the potential application of decarbonylation as an effective tool for C-C bond formation. This journal is

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Xu, Fan,Li, Yan-Jie,Huang, Chong,Xu, Hai-Chao

, p. 3820 - 3824 (2018/05/22)

A ruthenium-catalyzed electrochemical dehydrogenative annulation reaction of aniline derivatives and alkynes has been developed for the synthesis of indoles. Electric current is used to recycle the active ruthenium-based catalyst and promote H2 evolution. The electrolysis reaction is operationally convenient as it employs a simple undivided cell, proceeds efficiently in an aqueous solution, and is insensitive to air.

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