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7-Azaindole
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1H-Pyrrolo[2,3-b]pyridine
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USD $ 5.0-5.0 / Kilogram 1 Kilogram 1000 Kilogram/Month Enke Pharma-tech Co.,Ltd. (Cangzhou, China ) Contact Supplier

271-63-6 Usage

Chemical Properties

Brown-Cyrstalline Solid

Purification Methods

Recrystallise it repeatedly from EtOH, then sublime it in a vacuum [Tokumura et al. J Am Chem Soc 109 1346 1987]. The N-acetate has m 65-66o (from *C6H6), and the picrate has m 232-233o (from Me2CO) [Clemo & Swan J Chem Soc 603 1945, Beilstein 23 III/IV 1105.]

Uses

7-Azaindole is imidazolinone derivatives as CGRP receptor antagonists used in the treatment.
InChI:InChI=1/C7H6N2/c1-2-6-3-5-9-7(6)8-4-1/h1-5H,(H,8,9)

271-63-6 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (L07983)  7-Azaindole, 98%    271-63-6 1g 279.0CNY Detail
Alfa Aesar (L07983)  7-Azaindole, 98%    271-63-6 5g 825.0CNY Detail
Alfa Aesar (L07983)  7-Azaindole, 98%    271-63-6 25g 3179.0CNY Detail
Aldrich (A95502)  7-Azaindole  98% 271-63-6 A95502-1G 252.72CNY Detail
Aldrich (A95502)  7-Azaindole  98% 271-63-6 A95502-5G 663.39CNY Detail

271-63-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 7-Azaindole

1.2 Other means of identification

Product number -
Other names 1H-Pyrrolo[2,3-b]pyridine

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:271-63-6 SDS

271-63-6Synthetic route

1-(tert-butoxycarbonyl)-1H-pyrrolo<2,3-b>pyridine
138343-77-8

1-(tert-butoxycarbonyl)-1H-pyrrolo<2,3-b>pyridine

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With sodium carbonate In 1,2-dimethoxyethane; water for 20h; Heating;100%
With water at 100℃; for 1h;99%
With potassium phosphate In methanol at 120℃; under 5171.62 Torr; for 0.0333333h; Microwave irradiation;98%
tert-butyl (3-methylpyridin-2-yl)carbamate
138343-75-6

tert-butyl (3-methylpyridin-2-yl)carbamate

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
Stage #1: tert-butyl (3-methylpyridin-2-yl)carbamate With n-butyllithium; N,N-dimethyl-formamide In tetrahydrofuran at 0℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 50℃;
100%
With n-butyllithium In tetrahydrofuran; hexane; N,N-dimethyl-formamide at -15 - 25℃; for 17.5h;3.8 g
Stage #1: tert-butyl (3-methylpyridin-2-yl)carbamate With trimethylsilyl bromide In tetrahydrofuran; N,N-dimethyl-formamide at -30℃; for 1.75h; Inert atmosphere;
Stage #2: With hydrogenchloride In tetrahydrofuran; water; N,N-dimethyl-formamide at 0 - 40℃; for 3h;
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / 4 h / 0 °C
1.2: 0 °C
2.1: hydrogenchloride / water / 8 h / Reflux
View Scheme
methyl bromide
74-83-9

methyl bromide

tert-butyl (3-methylpyridin-2-yl)carbamate
138343-75-6

tert-butyl (3-methylpyridin-2-yl)carbamate

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
Stage #1: methyl bromide; tert-butyl (3-methylpyridin-2-yl)carbamate In diethyl ether at 0℃; for 4h;
Stage #2: With N,N-dimethyl-formamide In diethyl ether at 0℃; for 0.5h; Concentration;
99.1%
7-azaindoline
10592-27-5

7-azaindoline

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With carbon dioxide; DBN; Eosin Y In dimethyl sulfoxide at 25 - 30℃; for 48h; Irradiation;97%
With potassium tert-butylate In decane at 150℃; for 36h; Inert atmosphere; Schlenk technique;90%
With 4-tert-Butylcatechol; oxygen In water at 20℃; for 20h; Green chemistry;90%
(Z)-2-amino-3-(2-ethoxyethenyl)pyridine
146336-83-6

(Z)-2-amino-3-(2-ethoxyethenyl)pyridine

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With hydrogenchloride In methanol for 2h; Heating;94%
1-(2-amino-3-pyridinyl)-1-ethanone
65326-33-2

1-(2-amino-3-pyridinyl)-1-ethanone

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 90℃; pH=3; Temperature; pH-value; Microwave irradiation;93.2%
1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine
143141-23-5

1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With sodium t-butanolate In 1,4-dioxane at 80℃; for 3h; Inert atmosphere;93%
7-azaindole-2-carboxylic acid
136818-50-3

7-azaindole-2-carboxylic acid

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With zinc(II) oxide In toluene at 90℃; for 2h; Temperature;91.8%
1H-Pyrrolo[2,3-b]pyridine-7-oxide
55052-24-9

1H-Pyrrolo[2,3-b]pyridine-7-oxide

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With (4,4′-di-tert-butyl-2,2′-bipyridine)bis[(2-pyridinyl)phenyl]iridium(III) hexafluorophosphate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 2h; Inert atmosphere; Irradiation; chemoselective reaction;91%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In dichloromethane at 31℃; for 16h; Sealed tube; Irradiation;83%
With styrene; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; hydrazine hydrate In dimethyl sulfoxide at 20℃; for 13h; Inert atmosphere; Irradiation; chemoselective reaction;74%
1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine
348640-02-8

1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With cetyltrimethylammonim bromide; potassium hydroxide In tetrahydrofuran; water for 10h; Reagent/catalyst; Temperature; Time; Reflux; Green chemistry;90%
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Darkness; Schlenk technique;87%
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;70%
With caesium carbonate In tetrahydrofuran; methanol at 22℃; for 2h;
C7H6N4

C7H6N4

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With silver hexafluoroantimonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In benzene at 130℃; for 24h; Sealed tube; Glovebox; Inert atmosphere;86%
1H-pyrrolo[2,3-b]pyridine-3-carbonitrile
4414-89-5

1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With hydrogenchloride; water for 48h; Reflux; Large scale;72.9%
5-fluoro-1H-pyrrolo[2,3‐b]pyridine
866319-00-8

5-fluoro-1H-pyrrolo[2,3‐b]pyridine

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With 2-methyl-propan-1-ol; methanesulfonato(2-dicyclohexylphosphino -2’,6’-di-i-propoxy-1,1‘-biphenyl)(2’-amino-1,1’-biphenyl-2-yl)palladium(II); sodium tert-pentoxide In toluene at 80℃; for 48h; Sealed tube; Inert atmosphere;68%
tert-butyl (3-methylpyridin-2-yl)carbamate
138343-75-6

tert-butyl (3-methylpyridin-2-yl)carbamate

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

N,N-dimethyl-formamide

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
Stage #1: tert-butyl (3-methylpyridin-2-yl)carbamate With n-butyllithium In tetrahydrofuran at -10 - 0℃;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0 - 15℃;
Stage #3: With hydrogenchloride; water at -5 - 5℃;
67%
N-methyl-N-phenyl-N'-(2-(3-methylpyridine))formamidine
3189-06-8

N-methyl-N-phenyl-N'-(2-(3-methylpyridine))formamidine

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -20℃; for 5h; Reagent/catalyst; Inert atmosphere;65%
2-phenyloxepino[2,3-b]pyridine
933768-06-0

2-phenyloxepino[2,3-b]pyridine

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With acetamide; potassium tert-butylate In dimethyl sulfoxide at 80℃; for 48h; Inert atmosphere;52%
1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridnie

1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridnie

A

7-Azaindole
271-63-6

7-Azaindole

B

C10H14N2Si
1239864-85-7

C10H14N2Si

Conditions
ConditionsYield
With sodium t-butanolate In 1,4-dioxane at 80℃; for 3h; Inert atmosphere;A 44%
B 42%
3-ethenyl-2-nitropyridine
844503-09-9

3-ethenyl-2-nitropyridine

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 1,10-Phenanthroline; carbon monoxide In acetonitrile at 120℃; under 4560.31 Torr; for 180h;41%
1-acetyl-2,3-dihydropyrrolo<2,3-b>pyridine
111097-45-1

1-acetyl-2,3-dihydropyrrolo<2,3-b>pyridine

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With n-Dodecylamine In 1,2-dichloro-ethane for 1h; Irradiation;25%
(2-formylamino-pyridin-3-ylmethyl)-phosphonic acid diethyl ester

(2-formylamino-pyridin-3-ylmethyl)-phosphonic acid diethyl ester

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran; toluene at 90℃; for 0.5h;25%
1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde
4649-09-6

1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With perchloric acid adsorbed on silica gel; anthranilic acid amide In acetonitrile at 80℃; for 12h;25%
2-Amino-3-bromopyridine
13534-99-1

2-Amino-3-bromopyridine

Vinyl bromide
593-60-2

Vinyl bromide

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; XPhos In tert-butyl alcohol at 110℃; for 24h; Sealed tube; Inert atmosphere;9%
N-(3-methyl-2-pyridinyl)formamide
4931-46-8

N-(3-methyl-2-pyridinyl)formamide

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With sodium ethanolate at 350℃;
With sodium formate; sodium anilide at 290 - 310℃;
With hydrogenchloride In diethyl ether; water; pentane at -20℃; Inert atmosphere; Reflux;
1H-pyrrolo[2,3-b]pyridine-3,6-dicarboxylic acid
99066-81-6

1H-pyrrolo[2,3-b]pyridine-3,6-dicarboxylic acid

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
at 320 - 330℃;
oxirane
75-21-8

oxirane

3-bromo-1H-pyrrolo[2,3-b]pyridine
74420-15-8

3-bromo-1H-pyrrolo[2,3-b]pyridine

A

7-Azaindole
271-63-6

7-Azaindole

B

1-(2-hydroxyethyl)-7-azaindole
90929-77-4

1-(2-hydroxyethyl)-7-azaindole

C

3-(2-hydroxyethyl)-7-azaindole
90929-76-3

3-(2-hydroxyethyl)-7-azaindole

Conditions
ConditionsYield
With n-butyllithium 1.) ether, 1,2-dimethoxyethane, -5 deg C, 1 h; 2.) 0 deg C, 5 h; Yield given. Multistep reaction. Yields of byproduct given;
2,2-Dimethyl-N-[3-(2-oxo-ethyl)-pyridin-2-yl]-propionamide

2,2-Dimethyl-N-[3-(2-oxo-ethyl)-pyridin-2-yl]-propionamide

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
With hydrogenchloride for 8h; Heating; Yield given;
1-(1H-pyrrolo[2,3-b]pyridin-1-yl)ethanone
53277-42-2

1-(1H-pyrrolo[2,3-b]pyridin-1-yl)ethanone

A

7-Azaindole
271-63-6

7-Azaindole

B

n-pentyl halide

n-pentyl halide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / H2 / Pd-C / ethanol; 1,2-dimethoxy-ethane / 5 h / 20 °C
2: 25 percent / dodecylamine / 1,2-dichloro-ethane / 1 h / Irradiation
View Scheme
2,2-dimethyl-N-(3-methylpyridin-2-yl)propionamide
86847-66-7

2,2-dimethyl-N-(3-methylpyridin-2-yl)propionamide

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) n-BuLi / 1.) THF, -5 to 0 deg C, 4 h, 2.) THF, 0 deg C, 40 min
2: 5.5 M HCl / 8 h / Heating
View Scheme
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

7-Azaindole
271-63-6

7-Azaindole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 52 percent / 60percent NaH / benzene / 60 h / Heating
2: 74 percent / Pd(PPh3)2Cl2, Et4NCl / acetonitrile / 1 h / Heating
3: 78 percent / H2 / W-2 Raney Ni / methanol
4: 94 percent / conc. HCl / methanol / 2 h / Heating
View Scheme
7-Azaindole
271-63-6

7-Azaindole

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-chloro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one
83393-47-9

2-chloro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

Conditions
ConditionsYield
Stage #1: 7-Azaindole With aluminum (III) chloride In dichloromethane at 20℃; for 1.5h; Inert atmosphere;
Stage #2: chloroacetyl chloride In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;
100%
With aluminium trichloride In carbon disulfide at 50℃; for 2h;82%
With aluminium trichloride In carbon disulfide at 50℃; for 2h; Product distribution;81%
7-Azaindole
271-63-6

7-Azaindole

methyl iodide
74-88-4

methyl iodide

1-methyl-1H-pyrrolo[2,3-b]pyridine
27257-15-4

1-methyl-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
Stage #1: 7-Azaindole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere;
Stage #2: methyl iodide In N,N-dimethyl-formamide for 1h; Inert atmosphere;
100%
Stage #1: 7-Azaindole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere;
Stage #2: methyl iodide In N,N-dimethyl-formamide for 1h; Inert atmosphere;
100%
Stage #1: 7-Azaindole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;
98%
7-Azaindole
271-63-6

7-Azaindole

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

(2-trimethylethylsilylethoxy)methyl chloride

1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine
879132-46-4

1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
Stage #1: 7-Azaindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.25h;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil for 1.25h;
100%
Stage #1: 7-Azaindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.25h;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil for 1.25h;
100%
Stage #1: 7-Azaindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil for 1h;
100%
7-Azaindole
271-63-6

7-Azaindole

7-nitroquinoxaline-2(1H)-one
89898-96-4

7-nitroquinoxaline-2(1H)-one

7-nitro-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydro-1H-quinoxalin-2-one

7-nitro-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydro-1H-quinoxalin-2-one

Conditions
ConditionsYield
With trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 1h;100%
7-Azaindole
271-63-6

7-Azaindole

n-pentyl halide

n-pentyl halide

1-pentyl-1H-pyrrolo[2,3-b]pyridine
912562-57-3

1-pentyl-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
Stage #1: 7-Azaindole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: n-pentyl halide In N,N-dimethyl-formamide at 20℃; for 15h;
100%
7-Azaindole
271-63-6

7-Azaindole

iodobenzene
591-50-4

iodobenzene

1-phenyl-1H-pyrrolo[2,3-b]pyridine

1-phenyl-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
With potassium phosphate; trans-1,2-Diaminocyclohexane; copper(l) iodide In 1,4-dioxane at 110℃; for 24h;100%
With triethylamine In N,N-dimethyl-formamide at 110℃; for 3h;96%
With copper(l) iodide; manganese(II) fluoride; (1R,2R)-1,2-diaminocyclohexane; potassium hydroxide In water at 60℃; for 24h;93%
3-Bromopyridine
626-55-1

3-Bromopyridine

7-Azaindole
271-63-6

7-Azaindole

1-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine
847801-47-2

1-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
With potassium phosphate; trans-1,2-Diaminocyclohexane; copper(l) iodide In 1,4-dioxane at 110℃; for 95h;100%
7-Azaindole
271-63-6

7-Azaindole

1-Bromopentane
110-53-2

1-Bromopentane

1-pentyl-1H-pyrrolo[2,3-b]pyridine
912562-57-3

1-pentyl-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
Stage #1: 7-Azaindole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: 1-Bromopentane In N,N-dimethyl-formamide at 20℃; for 3.5h;
100%
Stage #1: 7-Azaindole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: 1-Bromopentane In N,N-dimethyl-formamide at 20℃; for 3.5h;
100%
Stage #1: 7-Azaindole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: 1-Bromopentane In N,N-dimethyl-formamide at 20℃; for 3.5h;
100%
7-Azaindole
271-63-6

7-Azaindole

1-bromo-hexane
111-25-1

1-bromo-hexane

C13H18N2
418795-22-9

C13H18N2

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃;100%
7-Azaindole
271-63-6

7-Azaindole

3-chloro-1H-pyrrolo[2,3-b]pyridine

3-chloro-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
With N-chloro-succinimide In tetrachloromethane; chloroform for 4h; Ambient temperature;99%
With 1-aza-4,6,11-trioxa-5-boratricyclo[3.3.3.0(1,5)]undecane; nickel diacetate; chlorine at 90℃; for 3h; Reflux;99.3%
With 1,3-dichloro-5,5-dimethylhydantoin In 1,4-dioxane at 80℃; for 0.5h;92%
With sodium hypochlorite; sodium azide; acetic acid In water; toluene at 20℃; for 0.5h;91%
With 1-chloro-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one In N,N-dimethyl-formamide at 20℃; for 12h; regioselective reaction;77%
7-Azaindole
271-63-6

7-Azaindole

lithium formate
556-63-8

lithium formate

1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde
4649-09-6

1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde

Conditions
ConditionsYield
With zinc diacetate In trifluoroacetic acid at 120℃; for 6h; Solvent; Concentration;99.1%
7-Azaindole
271-63-6

7-Azaindole

3-bromo-1H-pyrrolo[2,3-b]pyridine
74420-15-8

3-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
With 1-aza-4,6,11-trioxa-5-boratricyclo[3.3.3.0(1,5)]undecane; bromine; nickel diacetate at 100℃; for 3h; Temperature; Reflux;99%
With N-Bromosuccinimide In dichloromethane at 20℃; for 16h;96%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 4h; Cooling with ice;96%
7-Azaindole
271-63-6

7-Azaindole

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine
143141-23-5

1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
Stage #1: 7-Azaindole With tetrabutylammomium bromide; sodium hydroxide In dichloromethane
Stage #2: benzenesulfonyl chloride In dichloromethane at 0 - 20℃;
99%
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;98%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃; for 2h; Cooling with ice;95%
7-Azaindole
271-63-6

7-Azaindole

Z-ΔAla(N-Boc)-OMe
219851-84-0

Z-ΔAla(N-Boc)-OMe

Z-Ala[N-Boc-β-(7-azaindol-1-yl)]-OMe

Z-Ala[N-Boc-β-(7-azaindol-1-yl)]-OMe

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; Addition; Michael addition;99%
7-Azaindole
271-63-6

7-Azaindole

3,5-dimethylphenyl iodide
22445-41-6

3,5-dimethylphenyl iodide

1-(3,5-dimethylphenyl)-1H-pyrrolo[2,3-b]pyridine

1-(3,5-dimethylphenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane; dodecane at 110℃; for 24h;99%
With copper(I) oxide; potassium phosphate; N1,N2-bis(furan-2-ylmethyl)oxalamide In acetonitrile at 80℃;94%
With potassium phosphate monohydrate; iron(III) chloride hexahydrate; trans-N,N'-dimethylcyclohexane-1,2-diamine In water at 135℃; for 24h; Inert atmosphere;87%
7-Azaindole
271-63-6

7-Azaindole

n-butyl halide

n-butyl halide

N-butyl-7-azaindole
152956-02-0

N-butyl-7-azaindole

Conditions
ConditionsYield
Stage #1: 7-Azaindole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: n-butyl halide In N,N-dimethyl-formamide at 20℃; for 15h;
99%
7-Azaindole
271-63-6

7-Azaindole

tris(pentafluorophenyl)borate
1109-15-5

tris(pentafluorophenyl)borate

7-[tris(pentafluorophenyl)borane]-7-azaindole
879269-87-1

7-[tris(pentafluorophenyl)borane]-7-azaindole

Conditions
ConditionsYield
In dichloromethane (N2); a soln. of ligand added at room temp. to a soln. of B(C6F5)3, stirred for 1 h; evapd. (vac.); elem. anal.;99%
7-Azaindole
271-63-6

7-Azaindole

diethyl(methoxymethyl)amine
5888-29-9

diethyl(methoxymethyl)amine

N-((1H-pyrrolo[2,3-b]pyridin-1-yl)methyl)-N-ethylethanamine

N-((1H-pyrrolo[2,3-b]pyridin-1-yl)methyl)-N-ethylethanamine

Conditions
ConditionsYield
With hafnium tetrakis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 0.2h; Inert atmosphere; regioselective reaction;99%
3-iodopyridine
1120-90-7

3-iodopyridine

7-Azaindole
271-63-6

7-Azaindole

1-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine
847801-47-2

1-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
With manganese(II) fluoride; (S,S)-1,2-diaminocyclohexane; caesium carbonate In water at 130℃; for 24h; Reagent/catalyst;99%
With copper(l) iodide; manganese(II) fluoride; (1R,2R)-1,2-diaminocyclohexane; potassium hydroxide In water at 100℃; for 48h;94%
With copper(I) oxide; caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere;86%
7-Azaindole
271-63-6

7-Azaindole

bromopentene
1119-51-3

bromopentene

1-(pent-4-en-1-yl)-1H-pyrrolo[2,3-b]pyridine

1-(pent-4-en-1-yl)-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
Stage #1: 7-Azaindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere;
Stage #2: bromopentene In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;
99%
7-Azaindole
271-63-6

7-Azaindole

hexamethylenetetramine
100-97-0

hexamethylenetetramine

1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde
4649-09-6

1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde

Conditions
ConditionsYield
With propionic acid In ethanol at 80℃; for 6h; Temperature;98.9%
Stage #1: 7-Azaindole; hexamethylenetetramine With acetic acid for 6h; Duff reaction; Heating;
Stage #2: With water at 20℃; Further stages.;
77%
With acetic acid In water for 12h; Heating / reflux;76%
7-Azaindole
271-63-6

7-Azaindole

cyclopentyl trimethoxysilane
143487-47-2

cyclopentyl trimethoxysilane

7-azaindolidine cyclopentyl dimethoxy silane

7-azaindolidine cyclopentyl dimethoxy silane

Conditions
ConditionsYield
Stage #1: 7-Azaindole With n-butyllithium In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Cooling with ice;
Stage #2: cyclopentyl trimethoxysilane In tetrahydrofuran at 0 - 20℃; for 8h; Inert atmosphere;
98.3%
7-Azaindole
271-63-6

7-Azaindole

1-Phenylethanol
98-85-1, 13323-81-4

1-Phenylethanol

C15H14N2

C15H14N2

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 2h; Friedel-Crafts Alkylation;98.3%
7-Azaindole
271-63-6

7-Azaindole

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

7-Methoxycarbonylmethyl-1H-pyrrolo[2,3-b]pyridin-7-ium; bromide

7-Methoxycarbonylmethyl-1H-pyrrolo[2,3-b]pyridin-7-ium; bromide

Conditions
ConditionsYield
In benzene for 2h; Heating;98%
7-Azaindole
271-63-6

7-Azaindole

3-iodo-1H-pyrrolo[2,3-b]pyridine
23616-57-1

3-iodo-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
Stage #1: 7-Azaindole With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With iodine In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;
98%
With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.75h; Inert atmosphere;97%
With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃;97%
7-Azaindole
271-63-6

7-Azaindole

n-propyl halide

n-propyl halide

N-propyl-7-azaindole
942262-52-4

N-propyl-7-azaindole

Conditions
ConditionsYield
Stage #1: 7-Azaindole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: n-propyl halide In N,N-dimethyl-formamide at 20℃; for 15h;
98%
7-Azaindole
271-63-6

7-Azaindole

Phenyl glycidyl ether
122-60-1

Phenyl glycidyl ether

1-phenoxy-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)propan-2-ol
1017278-65-7

1-phenoxy-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)propan-2-ol

Conditions
ConditionsYield
ruthenium trichloride at 20℃; for 4h; Friedel-Crafts alkylation;98%
With ruthenium-exchanged FAU-Y zeolite at 20℃; for 0.5h; Friedel Crafts alkylation; Ultrasound irradiation; Neat (no solvent); regioselective reaction;98%

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