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51417-51-7 Usage

Chemical Properties

Beige-yellowish or brownish crystalline powder

Uses

7-Bromoindole may be used in the synthesis of the following:indoledyestuffs8-bromocarboline

General Description

7-Bromoindole is a 7-substituted indole derivative. Its synthesis from 7-bromoindole-2-carboxylic acid has been reported. It has been reported to reduce the production of staphyloxanthin in Staphylococcus aureus.

Check Digit Verification of cas no

The CAS Registry Mumber 51417-51-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,1,4,1 and 7 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 51417-51:
(7*5)+(6*1)+(5*4)+(4*1)+(3*7)+(2*5)+(1*1)=97
97 % 10 = 7
So 51417-51-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H6BrN/c9-7-3-1-2-6-4-5-10-8(6)7/h1-5,10H

51417-51-7 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (44422)  7-Bromoindole, 98%   

  • 51417-51-7

  • 0.25g

  • 142.0CNY

  • Detail
  • Alfa Aesar

  • (44422)  7-Bromoindole, 98%   

  • 51417-51-7

  • 1g

  • 567.0CNY

  • Detail
  • Alfa Aesar

  • (44422)  7-Bromoindole, 98%   

  • 51417-51-7

  • 5g

  • 2835.0CNY

  • Detail
  • Aldrich

  • (473723)  7-Bromoindole  96%

  • 51417-51-7

  • 473723-250MG

  • 2,160.99CNY

  • Detail
  • Aldrich

  • (473723)  7-Bromoindole  96%

  • 51417-51-7

  • 473723-1G

  • 5,023.98CNY

  • Detail
  • Aldrich

  • (473723)  7-Bromoindole  96%

  • 51417-51-7

  • 473723-5G

  • 13,969.80CNY

  • Detail

51417-51-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 7-Bromoindole

1.2 Other means of identification

Product number -
Other names RARECHEM AH BS 0083

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:51417-51-7 SDS

51417-51-7Synthetic route

7-bromo-N-(4-toluenesulfonyl)-1H-indole
189266-03-3

7-bromo-N-(4-toluenesulfonyl)-1H-indole

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;87%
1-(2-amino-3-bromophenyl)-2-chloroethan-1-one
74798-64-4

1-(2-amino-3-bromophenyl)-2-chloroethan-1-one

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
With sodium tetrahydroborate In 1,4-dioxane; water for 1h; Heating;84%
7-bromo-1-(pyrimidin-2-yl)-1H-indole

7-bromo-1-(pyrimidin-2-yl)-1H-indole

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
With sodium ethanolate In ethanol; dimethyl sulfoxide at 90℃; for 5h; Sealed tube; Inert atmosphere;79%
(2-Bromo-6-trimethylsilanylethynyl-phenyl)-carbamic acid tert-butyl ester
187099-50-9

(2-Bromo-6-trimethylsilanylethynyl-phenyl)-carbamic acid tert-butyl ester

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 2h; Heating;77%
7-bromoisatin
20780-74-9

7-bromoisatin

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
With potassium borohydride; dimethyl sulfate In toluene at -10 - -5℃; Inert atmosphere;74%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 48h;32%
7-bromo-2,3-dihydroindole
62813-85-8

7-bromo-2,3-dihydroindole

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
With salcomine; oxygen In methanol at 20℃; for 3h;73%
With salcomine In methanol for 11h; Ambient temperature;72%
With oxygen In N,N-dimethyl acetamide at 20℃; Schlenk technique; Irradiation;41%
2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
In tetrahydrofuran at -45 - -40℃; for 25h;72%
In tetrahydrofuran at -45℃; for 0.583333h;72%
Stage #1: 2-nitrophenyl bromide; vinyl magnesium bromide In tetrahydrofuran at -40 - 0℃; for 2.5h; Inert atmosphere;
Stage #2: With hydrogenchloride; pivalaldehyde In tetrahydrofuran; water at 0℃; for 72h; Inert atmosphere;
70%
(S)-7-bromo-tryptophan
75816-19-2

(S)-7-bromo-tryptophan

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; tryptophanase TnaA at 25℃; pH=7.4; Enzymatic reaction;63.2%
2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

A

2-oxoindole
59-48-3

2-oxoindole

B

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
In tetrahydrofuran at -40℃;A 30%
B 62%
2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

vinylmagnesium chloride
3536-96-7

vinylmagnesium chloride

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
In tetrahydrofuran at -70℃; for 3h; Cycloaddition;53%
7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole
642494-37-9

7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
With copper(ll) bromide In methanol; water at 80℃; for 4h;40%
[(E)-2-(3-Bromo-2-nitro-phenyl)-vinyl]-dimethyl-amine
105205-49-0

[(E)-2-(3-Bromo-2-nitro-phenyl)-vinyl]-dimethyl-amine

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
With zinc In acetic acid at 85℃; for 2h;29%
7-bromo-1H-indole-2-carboxylic acid
16732-71-1

7-bromo-1H-indole-2-carboxylic acid

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
With quinoline; copper(I) bromide at 250℃;
2,6-dibromoaniline
608-30-0

2,6-dibromoaniline

tributyl-((Z)-2-ethoxy-vinyl)-stannane
64724-29-4

tributyl-((Z)-2-ethoxy-vinyl)-stannane

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; tetraethylammonium chloride; oxalic acid 1.) MeCN, reflux, 4 h, 2.) MeCN, reflux, 3 h; Multistep reaction;
7-bromo-N-formylindoline
910808-42-3

7-bromo-N-formylindoline

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / aq. NaOH / methanol / 0.5 h / 75 °C
2: 73 percent / salcomine; O2 / methanol / 3 h / 20 °C
View Scheme
1-indoline
496-15-1

1-indoline

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 94 percent / EDCI; pyridine / 24 h / 20 °C
2.1: trifluoroacetic acid; thallium trifluoroacetate / 11 h / 20 °C
2.2: 73 percent / CuBr2 / dimethylformamide / 2 h / 135 °C
3.1: 94 percent / aq. NaOH / methanol / 0.5 h / 75 °C
4.1: 73 percent / salcomine; O2 / methanol / 3 h / 20 °C
View Scheme
N-formylindoline
2861-59-8

N-formylindoline

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: trifluoroacetic acid; thallium trifluoroacetate / 11 h / 20 °C
1.2: 73 percent / CuBr2 / dimethylformamide / 2 h / 135 °C
2.1: 94 percent / aq. NaOH / methanol / 0.5 h / 75 °C
3.1: 73 percent / salcomine; O2 / methanol / 3 h / 20 °C
View Scheme
2-iodophenylamine
615-43-0

2-iodophenylamine

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 86 percent / tetrahydrofuran / 114 h / Heating
2: 95 percent / triethylamine, Pd(PPh3)2Cl2, CuI / 0.25 h / Ambient temperature
3: 1.) tert-butyllithium, 2.) 1,2-dibromoethane / 1.) Et2O, pentane, -20 deg C, 3 h, 2.) Et2O, pentane, -100 deg C to r.t., overnight
4: 77 percent / sodium ethoxide / ethanol / 2 h / Heating
View Scheme
2-bromo-N-(tert-butoxycarbonyl)aniline
78839-75-5

2-bromo-N-(tert-butoxycarbonyl)aniline

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 50 percent / triethylamine, Pd(PPh3)2Cl2, CuI / 13 h / 100 °C
2: 1.) tert-butyllithium, 2.) 1,2-dibromoethane / 1.) Et2O, pentane, -20 deg C, 3 h, 2.) Et2O, pentane, -100 deg C to r.t., overnight
3: 77 percent / sodium ethoxide / ethanol / 2 h / Heating
View Scheme
tert-butyl 2-iodophenylcarbamate
161117-84-6

tert-butyl 2-iodophenylcarbamate

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / triethylamine, Pd(PPh3)2Cl2, CuI / 0.25 h / Ambient temperature
2: 1.) tert-butyllithium, 2.) 1,2-dibromoethane / 1.) Et2O, pentane, -20 deg C, 3 h, 2.) Et2O, pentane, -100 deg C to r.t., overnight
3: 77 percent / sodium ethoxide / ethanol / 2 h / Heating
View Scheme
2-bromoaniline
615-36-1

2-bromoaniline

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 89 percent / tetrahydrofuran / 91 h / Heating
2: 50 percent / triethylamine, Pd(PPh3)2Cl2, CuI / 13 h / 100 °C
3: 1.) tert-butyllithium, 2.) 1,2-dibromoethane / 1.) Et2O, pentane, -20 deg C, 3 h, 2.) Et2O, pentane, -100 deg C to r.t., overnight
4: 77 percent / sodium ethoxide / ethanol / 2 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 1.) BCl4, AlCl3, 2.) 2 N HCl / 1.) C6H6, CH2Cl2, reflux, 3 h, 2.) C6H6, CH2Cl2, 80 deg C, 45 min
2: 84 percent / NaBH4 / dioxane; H2O / 1 h / Heating
View Scheme
Multi-step reaction with 3 steps
1.1: hydroxylamine hydrochloride; hydrogenchloride; sodium sulfate / water / 0.08 h / 20 °C
1.2: 4.25 h / 20 - 90 °C
2.1: sulfuric acid / 0.5 h / 50 - 65 °C
3.1: borane-THF / tetrahydrofuran / 48 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride / water
2: sodium sulfate; hydroxylamine hydrochloride / water / 3 h / 35 - 85 °C
3: sulfuric acid / 0.08 h / 60 - 80 °C
4: potassium borohydride; dimethyl sulfate / toluene / -10 - -5 °C / Inert atmosphere
View Scheme
2-((trimethylsilyl)ethynyl)phenylaminocarboxylic acid tert-butyl ester
187099-49-6

2-((trimethylsilyl)ethynyl)phenylaminocarboxylic acid tert-butyl ester

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) tert-butyllithium, 2.) 1,2-dibromoethane / 1.) Et2O, pentane, -20 deg C, 3 h, 2.) Et2O, pentane, -100 deg C to r.t., overnight
2: 77 percent / sodium ethoxide / ethanol / 2 h / Heating
View Scheme
1-Acetyl-2,3-dihydro-1H-indole
16078-30-1

1-Acetyl-2,3-dihydro-1H-indole

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) thallium tris-trifluoroacetate (TTFA); 2.) CuBr2 / 1.) TFA, room temp., 3 h; 2.) DMF, room temp., 3 h
2: 96 percent / NaOH (40percent) / H2O; methanol / 0.5 h / Heating
3: 72 percent / salcomine / methanol / 11 h / Ambient temperature
View Scheme
1-acetyl-2,3-dihydro-7-bromoindole
114144-24-0

1-acetyl-2,3-dihydro-7-bromoindole

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / NaOH (40percent) / H2O; methanol / 0.5 h / Heating
2: 72 percent / salcomine / methanol / 11 h / Ambient temperature
View Scheme
1-acetyl-2,3-dihydro-7-iodoindole
104682-95-3

1-acetyl-2,3-dihydro-7-iodoindole

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 14 percent / Et3N / Pd(OAc)2 / dimethylformamide / 0.5 h / 115 °C
2: 1.) thallium tris-trifluoroacetate (TTFA); 2.) CuBr2 / 1.) TFA, room temp., 3 h; 2.) DMF, room temp., 3 h
3: 96 percent / NaOH (40percent) / H2O; methanol / 0.5 h / Heating
4: 72 percent / salcomine / methanol / 11 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 14 percent / Et3N, methyl acrylate / Pd(OAc)2 / dimethylformamide / 0.5 h / 115 °C
2: 1.) thallium tris-trifluoroacetate (TTFA); 2.) CuBr2 / 1.) TFA, room temp., 3 h; 2.) DMF, room temp., 3 h
3: 96 percent / NaOH (40percent) / H2O; methanol / 0.5 h / Heating
4: 72 percent / salcomine / methanol / 11 h / Ambient temperature
View Scheme
1-bromo-3-methyl-2-nitro-benzene
52414-97-8

1-bromo-3-methyl-2-nitro-benzene

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyrrolidine / dimethylformamide / 110 °C
2: 29 percent / Zn / acetic acid / 2 h / 85 °C
View Scheme
ethyl 7-bromo-1H-indole-2-carboxylate
16732-69-7

ethyl 7-bromo-1H-indole-2-carboxylate

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanolic alkaline solution
2: copper (I)-bromide; quinoline / 250 °C
View Scheme
2-(2-bromo-phenylhydrazono)-propionic acid

2-(2-bromo-phenylhydrazono)-propionic acid

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethanolic H2SO4
2: polyphosphoric acid
3: ethanolic alkaline solution
4: copper (I)-bromide; quinoline / 250 °C
View Scheme
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

o-fluorophenylboronic acid
1993-03-9

o-fluorophenylboronic acid

7-(2-FLUOROPHENYL)-1H-INDOLE
486447-30-7

7-(2-FLUOROPHENYL)-1H-INDOLE

Conditions
ConditionsYield
With sodium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 75℃; for 12h;100%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 7-bromo-1H-indole-1-carboxylate

tert-butyl 7-bromo-1H-indole-1-carboxylate

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 72h;100%
With dmap; triethylamine In dichloromethane at 20℃; for 16h;90%
With dmap; triethylamine In dichloromethane at 0℃; for 0.666667h; Inert atmosphere;90%
With dmap In acetonitrile for 1h;38%
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

3,4-(methylenedioxy)-benzeneboronic acid
94839-07-3

3,4-(methylenedioxy)-benzeneboronic acid

7-(3,4-methylenedioxyphenyl)indole
173267-18-0

7-(3,4-methylenedioxyphenyl)indole

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 96h; Heating;99%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

carbon monoxide
201230-82-2

carbon monoxide

N-[2-(4-fluorophenyl)ethyl]piperazine bis(hydrochloride salt)

N-[2-(4-fluorophenyl)ethyl]piperazine bis(hydrochloride salt)

(1H-indol-7-yl)-4-[2-(4-fluorophenethyl)]piperazin-1-yl-methanone

(1H-indol-7-yl)-4-[2-(4-fluorophenethyl)]piperazin-1-yl-methanone

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(benzonitrile)palladium(II) dichloride; triethylamine In toluene at 130℃; under 18751.5 Torr; for 20h;99%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

isopropyl bromide
75-26-3

isopropyl bromide

7-bromo-1-isopropyl-1H-indole
1147014-66-1

7-bromo-1-isopropyl-1H-indole

Conditions
ConditionsYield
Stage #1: 7-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.75h;
Stage #2: isopropyl bromide In N,N-dimethyl-formamide for 18h;
99%
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 2h;
Thiomorpholin
123-90-0

Thiomorpholin

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

4-(1H-indol-7-yl)thiomorpholine

4-(1H-indol-7-yl)thiomorpholine

Conditions
ConditionsYield
With [2-(2-aminoethyl)phenyl]-chloro-palladium di-tert-butyl-[2-(2,4,6-triisopropylphenyl)phenyl]phosphane; sodium t-butanolate In tetrahydrofuran at 85℃; for 12h; Inert atmosphere;98.79%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

benzyl bromide
100-39-0

benzyl bromide

1-benzyl-7-bromo-1H-indole
189634-91-1

1-benzyl-7-bromo-1H-indole

Conditions
ConditionsYield
Stage #1: 7-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.0833333h;
98%
With potassium hydroxide In N,N-dimethyl-formamide at 20℃;88%
With sodium hydride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;67.9%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

potassium (1-hexyn-1-yl)trifluoroborate

potassium (1-hexyn-1-yl)trifluoroborate

7-(1-hexyn-1-yl)indole

7-(1-hexyn-1-yl)indole

Conditions
ConditionsYield
With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran for 12h; Suzuki-Miyaura cross-coupling; Heating;97%
9-hydroxyxanthene
90-46-0

9-hydroxyxanthene

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

6-bromo-3-(9H-xanthen-9-yl)-1H-indole
1339113-09-5

6-bromo-3-(9H-xanthen-9-yl)-1H-indole

Conditions
ConditionsYield
With 1,3-dichloro-1,1,3,3-tetrabutylstannoxane In dichloromethane at 20℃; for 10h;97%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

benzalacetophenone
94-41-7

benzalacetophenone

3-(7-bromo-1H-indol-3-yl)-1,3-diphenylpropan-1-one

3-(7-bromo-1H-indol-3-yl)-1,3-diphenylpropan-1-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetonitrile at 50℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;97%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

(2-trimethylethylsilylethoxy)methyl chloride
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

7-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole
408354-54-1

7-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole

Conditions
ConditionsYield
Stage #1: 7-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide at 0℃; for 3h;
96%
Stage #1: 7-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide at 0℃; for 3h;
96%
Stage #1: 7-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide at 15℃; for 20h;
72.7%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

C17H18O5

C17H18O5

C24H20BrNO4

C24H20BrNO4

Conditions
ConditionsYield
In acetonitrile at 70℃; for 0.5h;95%
methanol
67-56-1

methanol

7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

7-bromo-3-methyl-1H-indole
86915-22-2

7-bromo-3-methyl-1H-indole

Conditions
ConditionsYield
With cobalt(II) tetrafluoroborate hexahydrate; tris(2-diphenylphosphinoethyl)phosphine; potassium carbonate at 100℃; for 24h; Autoclave; Glovebox; Inert atmosphere;95%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium tert-butylate at 140℃; for 17h;85%
With trimethylamine-N-oxide; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; potassium carbonate at 80℃; for 24h;82%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

benzaldehyde
100-52-7

benzaldehyde

3,3’-(phenylmethylene)bis(7-bromo-1H-indole)
1445721-28-7

3,3’-(phenylmethylene)bis(7-bromo-1H-indole)

Conditions
ConditionsYield
With 1,3-bis(mesityl)imidazolium chloride In dichloromethane at 20℃; for 1h; Schlenk technique;95%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

7-bromo-1 H-indole-3-carbaldehyde
115666-21-2

7-bromo-1 H-indole-3-carbaldehyde

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.666667h;
Stage #2: 7-bromo-1H-indole at 0 - 20℃; for 5.5h;
94%
With trichlorophosphate93%
With trichlorophosphate at 0 - 20℃; for 6h; Vilsmeier-Haack reaction;89%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

1-phenylmethylpiperazine
2759-28-6

1-phenylmethylpiperazine

carbon monoxide
201230-82-2

carbon monoxide

4-benzylpiperazine-1-yl-(1H-indol-7-yl)methanone

4-benzylpiperazine-1-yl-(1H-indol-7-yl)methanone

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(benzonitrile)palladium(II) dichloride; triethylamine In toluene at 130℃; under 18751.5 Torr; for 20h;94%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

4-(phenethyl)piperazine
5321-49-3

4-(phenethyl)piperazine

carbon monoxide
201230-82-2

carbon monoxide

1-(1H-indol-5-ylcarbonyl)-4-(2-phenylethyl)piperazine

1-(1H-indol-5-ylcarbonyl)-4-(2-phenylethyl)piperazine

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(benzonitrile)palladium(II) dichloride; triethylamine In toluene at 130℃; under 18751.5 Torr; for 20h;94%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

cyclohexanone
108-94-1

cyclohexanone

product 16/fig. 2.
1092574-95-2

product 16/fig. 2.

Conditions
ConditionsYield
With triethylsilane; trichloroacetic acid In toluene at 70℃;94%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

1-bromomethyl-3-trifluoromethylbenzene
402-23-3

1-bromomethyl-3-trifluoromethylbenzene

7-bromo-1-[3-(trifluoromethyl)benzyl]-1H-indole
1207969-48-9

7-bromo-1-[3-(trifluoromethyl)benzyl]-1H-indole

Conditions
ConditionsYield
Stage #1: 7-bromo-1H-indole With potassium hydroxide In dimethyl sulfoxide for 0.5h;
Stage #2: 1-bromomethyl-3-trifluoromethylbenzene In dimethyl sulfoxide
94%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

methyl 3-hydroxy-1H-indole-2-carboxylate
31827-04-0

methyl 3-hydroxy-1H-indole-2-carboxylate

methyl-2-(7-bromo-1H-indol-3-yl)-3-oxoindoline-2-carboxylate
1305155-43-4

methyl-2-(7-bromo-1H-indol-3-yl)-3-oxoindoline-2-carboxylate

Conditions
ConditionsYield
With C44H58CuN2O2; oxygen In 1,2-dichloro-ethane at 50℃; for 22h; Sealed tube; Inert atmosphere;94%
With ammonium cerium (IV) nitrate; sodium hydrogencarbonate In acetonitrile at 0 - 20℃;66%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

3-Phenylpropenol
104-54-1

3-Phenylpropenol

7-cinnamylindole
1219637-86-1

7-cinnamylindole

Conditions
ConditionsYield
With [2,2]bipyridinyl; manganese; nickel(II) bromide 2-methoxyethyl ether complex; zirconium(IV) chloride In N,N-dimethyl acetamide at 20 - 35℃;94%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

3,7-dibromoindole
78225-48-6

3,7-dibromoindole

Conditions
ConditionsYield
With pyridinium hydrobromide perbromide In pyridine at 0℃;93%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

3,4-Dimethoxyphenylboronic acid
122775-35-3

3,4-Dimethoxyphenylboronic acid

7-(3,4-Dimethoxy-phenyl)-1H-indole
173267-21-5

7-(3,4-Dimethoxy-phenyl)-1H-indole

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 96h; Heating;93%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

acetyl chloride
75-36-5

acetyl chloride

1-(7-bromo-1H-indol-3-yl)ethan-1-one
944086-09-3

1-(7-bromo-1H-indol-3-yl)ethan-1-one

Conditions
ConditionsYield
Stage #1: 7-bromo-1H-indole With diethylaluminium chloride In dichloromethane at 0℃; for 0.416667h;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 1 - 3h;
93%
With tin(IV) chloride In toluene90%
Stage #1: 7-bromo-1H-indole With diethylaluminium chloride In hexane; dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: acetyl chloride In hexane; dichloromethane at 0℃; Inert atmosphere;
Stage #1: 7-bromo-1H-indole; acetyl chloride In toluene at 0℃; for 0.166667h;
Stage #2: With tin(IV) chloride In toluene for 12h;
With tin(IV) chloride In toluene at 0 - 20℃; for 2h;
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

adrenosterone
382-45-6

adrenosterone

3-(7-bromo-1H-indol-3-yl)adrenosta-3,5-diene

3-(7-bromo-1H-indol-3-yl)adrenosta-3,5-diene

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In methanol; acetonitrile at 80℃; for 24h;93%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

epichlorohydrin
106-89-8

epichlorohydrin

C11H10BrNO

C11H10BrNO

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium hydroxide at 20℃;93%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

indole
120-72-9

indole

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene at 110℃; for 12h;92%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; cesium acetate; isopropyl alcohol at 100℃; Schlenk technique; Inert atmosphere;65%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

methyl iodide
74-88-4

methyl iodide

7-bromo-1-methylindole
280752-68-3

7-bromo-1-methylindole

Conditions
ConditionsYield
Stage #1: 7-bromo-1H-indole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.75h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;
92%
Stage #1: 7-bromo-1H-indole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; for 0.0833333h;
85%
Stage #1: 7-bromo-1H-indole With sodium hydride In tetrahydrofuran at 0℃; for 1h;
Stage #2: methyl iodide In tetrahydrofuran
85%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

C21H16BrN

C21H16BrN

Conditions
ConditionsYield
With phosphomolybdic acid In ethylenediamine at 60℃; for 1h;92%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

3-(tetrahydro-2-methyl-2-furyl)-7-bromo-1H-indole

3-(tetrahydro-2-methyl-2-furyl)-7-bromo-1H-indole

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 40℃;92%

51417-51-7Relevant articles and documents

7-Pyridylindoles: Synthesis, structure, and properties

Mudadu, Maria Salvatora,Singh, Ajay,Thummel, Randolph P.

, p. 7611 - 7617 (2006)

(Chemical Equation Presented) A series of three isomeric 7-pyridylindoles (7-PIs) are prepared where the pyridine attachment is through C2, C3, or C4. These systems are prepared by a combination of the Bartoli reaction and the Stille coupling with an appropriate pyridyl stannane. By treatment with CH 3I, the 7-PIs can be converted to their pyridinium salts. Deprotonation at the NH of these salts leads to a zwitterion which, in the 4-pyridyl system, also exists as a neutral isomer. The photophysical and NMR properties of these systems are discussed. All three pyridylindoles are analyzed by X-ray crystallography and shown to exist in different states of aggregation dictated by the formation of intra- and intermolecular H-bonds.

CONDENSED HETEROAROMATIC RING SYSTEMS. XXIII. A CONCISE SYNTHESIS OF HIPPADINE

Sakamoto, Takao,Yasuhara, Akito,Kondo, Yoshinori,Yamanaka, Hiroshi

, p. 2597 - 2600 (1993)

Hippadine, a pyrrolophenanthridine alkaloid, was synthesized in 39percent overall yield of three steps using the palladium-catalyzed cross-coupling reaction of 2,6-dibromoaniline with (Z)-1-tributylstannyl-2-ethoxyethene as a key step.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo

supporting information, p. 7738 - 7744 (2021/05/07)

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Pd-Catalyzed C-H Halogenation of Indolines and Tetrahydroquinolines with Removable Directing Group

Ahmad, Ashfaq,Dutta, Himangsu Sekhar,Kumar, Mohit,Khan, Afsar Ali,Raziullah,Koley, Dipankar

, p. 5870 - 5875 (2020/07/30)

Pd-catalyzed directing-group-assisted regioselective halogenations to C7 of indolines and C8 of tetrahydroquinolines were achieved in good to excellent yields. The practicality and utility of the developed method have been illustrated by various functiona

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