271-63-6

Basic information

• Product Name: 7-Azaindole
• Synonyms: 1,7-Diaza-1H-indene;7-Aza-7H-indole;7-Dideazapurine;7-Azaindole, 98% 5GR;NSC 67063;NSC 77951;7-AZAINDOLE FOR SYNTHESIS 1 G;7-Azaindole SynonyMs 1H-Pyrrolo[2,3-b]pyridine
• CAS NO: 271-63-6
• Molecular Formula: C₇H₆N₂
• Molecular Weight: 118.14
• EINECS: 205-981-0
• Product Categories: Heterocycles series;Indole;Heterocyclic Compounds;Indole Series;Indole Derivatives;Pharmaceutical intermediate;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Heterocycle-Indole series;Heterocycle-Pyridine series;buildingblock;Halogenated Heterocycles ,Thiazoles;blocks;IndolesOxindoles;Heterocycles
• Mol File: 271-63-6.mol
• Article Data: 55

Chemical Properties

• Melting Point: 105-107 °C(lit.)
• Boiling Point: 270 °C (753.1004 mmHg)
• Flash Point: 270°C
• Appearance: White to off-white/Powder
• Density: 1.1151 (rough estimate)
• Vapor Pressure: 0.0094mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• PKA: 7.69±0.20(Predicted)
• BRN: 109667
• CAS DataBase Reference: 7-Azaindole(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Azaindole(271-63-6)
• EPA Substance Registry System: 7-Azaindole(271-63-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36-41-37/38-22
• Safety Statements: 39-26-36/37/39
• WGK Germany: 3
• RTECS: UY8710000
• HazardClass: IRRITANT
• Hazardous Substances Data: 271-63-6(Hazardous Substances Data)

Usage

Chemical Properties

Brown-Cyrstalline Solid

Uses

7-Azaindole is imidazolinone derivatives as CGRP receptor antagonists used in the treatment.A heterocyclic molecule that can be utilized as a pharmaceutical building block.Starting material in a recent synthesis of azaserotonin.

Application

7-Azaindole is a heterocyclic organic compound, which is an organic synthesis intermediate and a pharmaceutical intermediate. It is the core structure of many drugs, such as antitumor drugs, dopamine D4 receptors, p38 kinase inhibitors, thrombin inhibitors, etc.

Preparation

Synthesis of 7-azaindole: in a single-necked flask, add 2.0 g of 2-amino-3-methylpyridine and 2.5 g of N-Methylformanilide into 40 mL of dichloromethane, and add 3.15 g of PCl with stirring under an ice-water bath. After 4 hours of reaction, the reaction system was slowly poured into 40 mL of ammonia water, and the insoluble matter was removed by suction filtration. The organic layer was separated, washed twice with water, dried over anhydrous sodium sulfate, and evaporated to dryness to obtain 2.91 g of 7-azaindole as a pale yellow solid, with a yield of 70%.

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.]

InChI:InChI=1/C7H6N2/c1-2-6-3-5-9-7(6)8-4-1/h1-5H,(H,8,9)

Synthetic route

1-(tert-butoxycarbonyl)-1H-pyrrolo<2,3-b>pyridine (138343-77-8) → 7-Azaindole (271-63-6)

Conditions	Yield
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) → 7-Azaindole (271-63-6)

Conditions	Yield
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) + tert-butyl (3-methylpyridin-2-yl)carbamate (138343-75-6) → 7-Azaindole (271-63-6)

Conditions	Yield
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-Azaindole (271-63-6)

Conditions	Yield
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) → 7-Azaindole (271-63-6)

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating;	94%

1-(2-amino-3-pyridinyl)-1-ethanone (65326-33-2) → 7-Azaindole (271-63-6)

Conditions	Yield
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) → 7-Azaindole (271-63-6)

Conditions	Yield
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 (271-63-6)

Conditions	Yield
With zinc(II) oxide In toluene at 90℃; for 2h; Temperature;	91.8%

1H-Pyrrolo[2,3-b]pyridine-7-oxide (55052-24-9) → 7-Azaindole (271-63-6)

Conditions	Yield
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) → 7-Azaindole (271-63-6)

Conditions	Yield
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 → 7-Azaindole (271-63-6)

Conditions	Yield
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) → 7-Azaindole (271-63-6)

Conditions	Yield
With hydrogenchloride; water for 48h; Reflux; Large scale;	72.9%

5-fluoro-1H-pyrrolo[2,3‐b]pyridine (866319-00-8) → 7-Azaindole (271-63-6)

Conditions	Yield
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) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 7-Azaindole (271-63-6)

Conditions	Yield
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) → 7-Azaindole (271-63-6)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -20℃; for 5h; Reagent/catalyst; Inert atmosphere;	65%

2-phenyloxepino[2,3-b]pyridine (933768-06-0) → 7-Azaindole (271-63-6)

Conditions	Yield
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 → 7-Azaindole (271-63-6) + C10H14N2Si (1239864-85-7)

Conditions	Yield
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) → 7-Azaindole (271-63-6)

Conditions	Yield
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) → 7-Azaindole (271-63-6)

Conditions	Yield
With n-Dodecylamine In 1,2-dichloro-ethane for 1h; Irradiation;	25%

(2-formylamino-pyridin-3-ylmethyl)-phosphonic acid diethyl ester → 7-Azaindole (271-63-6)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; toluene at 90℃; for 0.5h;	25%

1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde (4649-09-6) → 7-Azaindole (271-63-6)

Conditions	Yield
With perchloric acid adsorbed on silica gel; anthranilic acid amide In acetonitrile at 80℃; for 12h;	25%

2-Amino-3-bromopyridine (13534-99-1) + Vinyl bromide (593-60-2) → 7-Azaindole (271-63-6)

Conditions	Yield
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) → 7-Azaindole (271-63-6)

Conditions	Yield
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) → 7-Azaindole (271-63-6)

Conditions	Yield
at 320 - 330℃;

oxirane (75-21-8) + 3-bromo-1H-pyrrolo[2,3-b]pyridine (74420-15-8) → 7-Azaindole (271-63-6) + 1-(2-hydroxyethyl)-7-azaindole (90929-77-4) + 3-(2-hydroxyethyl)-7-azaindole (90929-76-3)

Conditions	Yield
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 → 7-Azaindole (271-63-6)

Conditions	Yield
With hydrogenchloride for 8h; Heating; Yield given;

1-(1H-pyrrolo[2,3-b]pyridin-1-yl)ethanone (53277-42-2) → 7-Azaindole (271-63-6) + n-pentyl halide

Conditions	Yield
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) → 7-Azaindole (271-63-6)

Conditions	Yield
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) → 7-Azaindole (271-63-6)

Conditions	Yield
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) + chloroacetyl chloride (79-04-9) → 2-chloro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one (83393-47-9)

Conditions	Yield
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) + methyl iodide (74-88-4) → 1-methyl-1H-pyrrolo[2,3-b]pyridine (27257-15-4)

Conditions	Yield
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) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (879132-46-4)

Conditions	Yield
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-nitroquinoxaline-2(1H)-one (89898-96-4) → 7-nitro-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydro-1H-quinoxalin-2-one

Conditions	Yield
With trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 1h;	100%

7-Azaindole (271-63-6) + n-pentyl halide → 1-pentyl-1H-pyrrolo[2,3-b]pyridine (912562-57-3)

Conditions	Yield
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) + iodobenzene (591-50-4) → 1-phenyl-1H-pyrrolo[2,3-b]pyridine

Conditions	Yield
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) + 7-Azaindole (271-63-6) → 1-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine (847801-47-2)

Conditions	Yield
With potassium phosphate; trans-1,2-Diaminocyclohexane; copper(l) iodide In 1,4-dioxane at 110℃; for 95h;	100%

7-Azaindole (271-63-6) + 1-Bromopentane (110-53-2) → 1-pentyl-1H-pyrrolo[2,3-b]pyridine (912562-57-3)

Conditions	Yield
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) + 1-bromo-hexane (111-25-1) → C13H18N2 (418795-22-9)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃;	100%

7-Azaindole (271-63-6) → 3-chloro-1H-pyrrolo[2,3-b]pyridine

Conditions	Yield
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) + lithium formate (556-63-8) → 1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde (4649-09-6)

Conditions	Yield
With zinc diacetate In trifluoroacetic acid at 120℃; for 6h; Solvent; Concentration;	99.1%

7-Azaindole (271-63-6) → 3-bromo-1H-pyrrolo[2,3-b]pyridine (74420-15-8)

Conditions	Yield
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) + benzenesulfonyl chloride (98-09-9) → 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine (143141-23-5)

Conditions	Yield
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) + Z-ΔAla(N-Boc)-OMe (219851-84-0) → Z-Ala[N-Boc-β-(7-azaindol-1-yl)]-OMe

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; Addition; Michael addition;	99%

7-Azaindole (271-63-6) + 3,5-dimethylphenyl iodide (22445-41-6) → 1-(3,5-dimethylphenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions	Yield
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) + n-butyl halide → N-butyl-7-azaindole (152956-02-0)

Conditions	Yield
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) + tris(pentafluorophenyl)borate (1109-15-5) → 7-[tris(pentafluorophenyl)borane]-7-azaindole (879269-87-1)

Conditions	Yield
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) + diethyl(methoxymethyl)amine (5888-29-9) → N-((1H-pyrrolo[2,3-b]pyridin-1-yl)methyl)-N-ethylethanamine

Conditions	Yield
With hafnium tetrakis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 0.2h; Inert atmosphere; regioselective reaction;	99%

3-iodopyridine (1120-90-7) + 7-Azaindole (271-63-6) → 1-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine (847801-47-2)

Conditions	Yield
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) + bromopentene (1119-51-3) → 1-(pent-4-en-1-yl)-1H-pyrrolo[2,3-b]pyridine

Conditions	Yield
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) + hexamethylenetetramine (100-97-0) → 1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde (4649-09-6)

Conditions	Yield
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) + cyclopentyl trimethoxysilane (143487-47-2) → 7-azaindolidine cyclopentyl dimethoxy silane

Conditions	Yield
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) + 1-Phenylethanol (98-85-1, 13323-81-4) → C15H14N2

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 2h; Friedel-Crafts Alkylation;	98.3%

7-Azaindole (271-63-6) + bromoacetic acid methyl ester (96-32-2) → 7-Methoxycarbonylmethyl-1H-pyrrolo[2,3-b]pyridin-7-ium; bromide

Conditions	Yield
In benzene for 2h; Heating;	98%

7-Azaindole (271-63-6) → 3-iodo-1H-pyrrolo[2,3-b]pyridine (23616-57-1)

Conditions	Yield
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) + n-propyl halide → N-propyl-7-azaindole (942262-52-4)

Conditions	Yield
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) + Phenyl glycidyl ether (122-60-1) → 1-phenoxy-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)propan-2-ol (1017278-65-7)

Conditions	Yield
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%

Upstream product

• 75-21-8 oxirane 
• 74420-15-8 3-bromo-1H-pyrrolo[2,3-b]pyridine 
• 2037-31-2 3-chlorophenylthiol 
• 23616-57-1 3-iodo-1H-pyrrolo[2,3-b]pyridine 
• 183208-35-7 5-bromo-1H-pyrrolo[2,3-b]pyridine 
• 55052-24-9 1H-Pyrrolo[2,3-b]pyridine-7-oxide 
• 161264-46-6 1-H-pyrrolo<2,3-b>pyridin-1-amine 
• 73183-34-3 bis(pinacol)diborane 
• 348640-06-2 4-bromo-7-azaindole 
• 866319-00-8 5-fluoro-1H-pyrrolo[2,3‐b]pyridine 
• 65326-33-2 1-(2-amino-3-pyridinyl)-1-ethanone 
• 3189-06-8 N-methyl-N-phenyl-N'-(2-(3-methylpyridine))formamidine 
• 10592-27-5 7-azaindoline 
• 54230-88-5 8-bromotetrazolo[1,5-a]pyridine 

Downstream Products

• 90929-77-4 1-(2-hydroxyethyl)-7-azaindole 
• 53277-42-2 1-(1H-pyrrolo[2,3-b]pyridin-1-yl)ethanone 
• 15432-17-4 N₇-benzyl-7-azaindole 
• 152955-68-5 1-benzyl-1H-pyrrolo[2,3-b]-pyridine 
• 83393-46-8 1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one 
• 79960-49-9 Benzoic acid cyano-phenyl-pyrrolo[2,3-b]pyridin-1-yl-methyl ester 
• 83393-47-9 2-chloro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one 
• 90929-73-0 2-bromo-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one 
• 74420-18-1 7-Hydroxy-1H-pyrrolo<2,3-b>pyridinium m-chlorobenzoate 
• 75614-69-6 7-Methyl-1H-pyrrolo<2,3-b>pyridinium p-toluenesulfonate 
• 27257-15-4 1-methyl-1H-pyrrolo[2,3-b]pyridine 
• 113423-51-1 3,3-Dibromo-1,3-dihydro-2H-pyrrolo[2,3-b]-pyridin-2-one 
• 55052-24-9 1H-Pyrrolo[2,3-b]pyridine-7-oxide 
• 183001-71-0 1-(tert-butyldimethylsilyl)-7-azaindole 

Relevant articles and documents

Ruthenium-Catalyzed Regioselective C(sp2)-H Activation/Annulation of N-(7-Azaindole)amides with 1,3-Diynes Using N-Amino-7-azaindole as the N, N-Bidentate Directing Group

The ruthenium(II)-catalyzed regioselective annulation of N-(7-azaindole)amides with 1,3-diynes has been demonstrated. Bioactive N-amino-7-azaindole has been used as a new bidentate directing group to furnish an array of 3-alkynylated isoquinolones. Furthermore, the developed protocol works efficiently for both aryl- and heteroaryl-substituted amides producing a range of pharmacologically useful 7-azaindole-based isoquinolones with a wide range of functionality.

Photochemistry of Transient Tautomer of 7-Azaindole H-Bonded Dimer Studied by Two-Step Laser Excitation Fluorescence Measurements

Formation of the monomeric tautomer (7H-pyrrolopyridine) in the photodissociation of the transient groun-state dimeric tautomer, generated via excited-state double proton transfer of 7-azaindole H-bonded dimer in 3-methylpentane (MP), was confirmled by transient absorption and two-step laser excitation (TSLE) fluorescence spectroscopies.The intense XeCl laser pulse (308-nm) excitation of the H-bonded dimer in MP at room temperature produced short- (17 μs) and a long-lived (47 μs) transients.The former and latter were ascribed to the dimeric and monomeric tautomers in the ground state, respectively.It is suggested that the second pulse excitation of the short-lived dimeric tautomer induces efficient dissociation to form a monomeric tautomer in the xcited state together with that in the ground state.One-color (308-nm) biphotonic processes within the XeCl laser pulse are therefore responsible for the long-lived monomeric tautomer in the ground state.The decay of the monomeric tautomer in the dark is attributable to the H-transfer reaction to yield 7-azaindole.Significant deuterium isotope effects were found for H-transfer of the monomeric tautomer as well as for photodissociation of the dimeric tautomer.

Solvation of 7-azaindole in alcohols and water: Evidence for concerted, excited-state, double-proton transfer in alcohols

The proton inventory technique is used for the first time to investigate excited-state proton-transfer processes. The nonradiative pathways of the biological probe, 7-azaindole, in methanol, ethanol, and water are examined. Results in methanol and ethanol demonstrate the involvement of two protons in the transition state for the excited-state double-proton transfer process. These data provide the first experimental evidence suggesting a concerted tautomerization reaction of 7-azaindole in alcohols. The data for 7-azaindole in water are interpreted in terms of a nonradiative pathway that is qualitatively different from that in alcohols. We propose abstraction of the N1 hydrogen by water as a possible nonradiative decay process.

Palladium-catalyzed hydrodefluorination of fluoroarenes

-

Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen

The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.