272-49-1

Basic information

• Product Name: 4-Azaindole
• Synonyms: 4-AZAINDOLE;1H-PYRROLO[3.2-B]PYRIDINE;1,4-DIAZAINDENE;4-AZAINDOLE, 98+%;4-Aza-1H-indole;4-Azaindole,1H-pyrrolo[3,2-b]pyridine;4-Azindole;Pyrrolo Pyridine derivative
• CAS NO: 272-49-1
• Molecular Formula: C₇H₆N₂
• Molecular Weight: 118.14
• EINECS: 1592732-453-0
• Product Categories: Indoles and derivatives;Indole;Heterocyclic Compounds;Indole Series;Indoles;Azaindole;Building Blocks;Azaindoles;Heterocycle-Indole series
• Mol File: 272-49-1.mol
• Article Data: 24

Chemical Properties

• Melting Point: 126-127°C
• Boiling Point: 273.782 °C at 760 mmHg
• Flash Point: 124.839 °C
• Appearance: /Solid
• Density: 1.242 g/cm³
• Vapor Pressure: 0.009mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 14.66±0.30(Predicted)
• Water Solubility: Soluble in methanol and chloroform. Slightly soluble in water.
• CAS DataBase Reference: 4-Azaindole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Azaindole(272-49-1)
• EPA Substance Registry System: 4-Azaindole(272-49-1)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• RTECS: UY8715000
• HazardClass: IRRITANT
• Hazardous Substances Data: 272-49-1(Hazardous Substances Data)

Usage

Chemical Properties

prisms

Uses

Different sources of media describe the Uses of 272-49-1 differently. You can refer to the following data:
1. 4-Azaindole is used a reagent for the creation of complex molecules. When combined with a bisalkoxyalkyl spacer, they can be used to target melatonin MT 1 receptors over MT 2 receptors.
2. It is an important raw material and intermediate used in organic synthesis agrochemical, pharmaceutical and dyestuff field.

Application

4-Azaindole is an important raw material and intermediate used in organic synthesis agrochemical, pharmaceutical and dyestuff field.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 29, p. 359, 1992 DOI: 10.1002/jhet.5570290213

Precautions

Store in cool, dry place in tightly closed container. With adequate ventilation. Store away from oxidizing agent.

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

Synthetic route

1-(1H-pyrrolo[3,2-b]pyridin-1-yl)ethanone (24509-73-7) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
With potassium carbonate In methanol	100%

2-((trimethylsilyl)ethynyl)pyridin-3-amine (947330-64-5) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; acetonitrile at 20℃; for 2h;	97%
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 20℃; for 5h;	70%

2-(3-nitro-2-pyridinyl)-N,N-dimethyletheneamine (65156-92-5) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal	95%
With formic acid; palladium 10% on activated carbon In methanol for 4h; Inert atmosphere;	71%
With hydrogenchloride; iron In 1,4-dioxane; methanol at 80℃; for 3h;
With palladium 10% on activated carbon; hydrogen In ethanol	15 mg

2-(3-nitropyridin-2-yl)acetonitrile (123846-65-1) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 24h;	89%
With palladium 10% on activated carbon; hydrogen at 20℃; for 24h;	85%
With hydrogen; sodium hydrogencarbonate; palladium In ethanol; water; acetic acid	68%
With palladium 10% on activated carbon; hydrogen; acetic acid In ethanol at 20℃; under 2844.39 Torr; for 24h;	68%

(E)-3-amino-2-(2-ethoxyethenyl)pyridine (146336-81-4) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating;	88%

(2-trimethylsilanylethynylpyridin-3-yl) carbamic acid tert-butyl ester (849353-49-7) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 8h; Heating / reflux;	79%

(E)-N,N-dimethyl-2-(3-nitropyridin-2-yl)ethenamine (65156-92-5) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
With formic acid; palladium 10% on activated carbon In methanol for 4h; Inert atmosphere;	71%
With hydrogen; palladium on activated charcoal	37%
With formic acid; palladium on activated charcoal In methanol for 4h;	0.31 g
With formic acid; palladium 10% on activated carbon In methanol for 4h; Inert atmosphere;
With iron(III) chloride; hydrazine hydrate In methanol; water at 25 - 70℃;

2-ethenyl-3-nitropyridine (150281-83-7) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 1,10-Phenanthroline; carbon monoxide In acetonitrile at 120℃; under 4560.31 Torr; for 42h;	65%

(2-Trimethylsilanylethynyl-pyridin-3-yl)carbamic acid ethyl ester (112671-57-5) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
With sodium ethanolate In ethanol for 1h; Heating / reflux;	63.5%
With sodium ethanolate In ethanol for 1h; Heating / reflux;	63.5%
With sodium ethanolate In ethanol Heating; Yield given;

3-amino-2-(2,2-diethoxyethyl)pyridine (107469-27-2) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
With hydrogenchloride In ethanol for 1h; Heating;	56%

tert-butyl N-(2-methylpyridin-3-yl)carbamate (1219095-87-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Stage #1: tert-butyl N-(2-methylpyridin-3-yl)carbamate With n-butyllithium In tetrahydrofuran; hexane at -15 - 0℃; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 0 - 20℃; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at 45℃; Cooling;	40%

N-(2-methyl-[3]pyridyl)-formamide (116286-64-7) + potassium ethoxide (917-58-8) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
at 350℃;

N-(2-methyl-[3]pyridyl)-formamide (116286-64-7) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
With potassium ethoxide at 350℃;

2-chloro-3-aminopyridine (6298-19-7) + acetaldehyde (75-07-0) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
With potassium tert-butylate 1.) Et2O, NH3 liquid, -33 deg C, 2.) Et2O, NH3 liquid, irrad., -33 deg C, 100 min.; Yield given. Multistep reaction;

2-(2,2-diethoxyethyl)-3-nitropyridine (107479-62-9) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal
Multi-step reaction with 2 steps 1: 80 percent / H2 / 5 percent Pd-C / ethanol / Ambient temperature 2: 56 percent / conc. HCl / ethanol / 1 h / Heating View Scheme

2-Chloro-3-nitropyridine (5470-18-8) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 50 percent / triethylamine; CuI / Pd(PPh3)4 / acetonitrile / 4 h / 20 °C 2: 60 percent / tin(II) chloride dihydrate; NH4Cl / ethanol / 4 h / 60 °C 3: 70 percent / potassium tert-butoxide / 1-methyl-pyrrolidin-2-one / 5 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: NaH / dimethylformamide 1.2: 50 percent / dimethylformamide / 1 h 2.1: 86 percent / aq. HCl / 8 h / Heating 3.1: dimethylformamide / 4.25 h / 90 °C 4.1: 0.31 g / HCOOH / Pd/C / methanol / 4 h View Scheme
Multi-step reaction with 3 steps 1: 43 percent / K2CO3 / (PPh3)4Pd / dioxane / 48 h / Heating 2: dimethylformamide / 4.25 h / 90 °C 3: 0.31 g / HCOOH / Pd/C / methanol / 4 h View Scheme

3-nitro-2-[2-(trimethylsilyl)ethynyl]pyridine (107469-26-1) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / tin(II) chloride dihydrate; NH4Cl / ethanol / 4 h / 60 °C 2: 70 percent / potassium tert-butoxide / 1-methyl-pyrrolidin-2-one / 5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: NaOEt / ethanol 2: 1.) H2; 2.) HCl / 1.) Pd/C View Scheme
Multi-step reaction with 3 steps 1: ethanol / 3 h / Heating 2: 80 percent / H2 / 5 percent Pd-C / ethanol / Ambient temperature 3: 56 percent / conc. HCl / ethanol / 1 h / Heating View Scheme

2-methyl-3-nitropyridine (18699-87-1) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 4.25 h / 90 °C 2: 0.31 g / HCOOH / Pd/C / methanol / 4 h View Scheme
Multi-step reaction with 2 steps 1: 100 percent 2: 95 percent / H2 / Pd/C View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 4 h / 90 °C / Inert atmosphere 2: formic acid / palladium 10% on activated carbon / methanol / 4 h / Inert atmosphere View Scheme

diethyl 2-(3-nitropyridin-2-yl)malonate (64362-41-0) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / aq. HCl / 8 h / Heating 2: dimethylformamide / 4.25 h / 90 °C 3: 0.31 g / HCOOH / Pd/C / methanol / 4 h View Scheme

(E)-2-(2-ethoxyetenyl)-3-nitropyridine (146336-73-4) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / H2 / W-2 Raney Ni / methanol 2: 88 percent / conc. HCl / methanol / 2 h / Heating View Scheme

3-amino-2-bromopyridine (39856-58-1) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 58 percent / pyridine / 3 h / 0-10 deg C 2: CuI, Et3N / Pd(PPh3)2Cl2 / 100 - 110 °C 3: NaOEt / ethanol / Heating View Scheme
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 6 h / 60 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran; acetonitrile / 2 h / 20 °C View Scheme

2-bromo-3-nitropyridine (19755-53-4) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: CuI, Et3N / Pd(PPh3)2Cl2 / 100 - 110 °C 2: NaOEt / ethanol 3: 1.) H2; 2.) HCl / 1.) Pd/C View Scheme

ethyl 2-bromo-3-pyridinecarbamate (112671-55-3) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: CuI, Et3N / Pd(PPh3)2Cl2 / 100 - 110 °C 2: NaOEt / ethanol / Heating View Scheme

3-nitro-2,6-lutidine (15513-52-7) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 62 percent / ZnCl2, N,N-dimethylformamide / 24 h / 100 °C 2: 1.) ozonized oxygen, 2.) hydrogen peroxide 3: 100 percent 4: 95 percent / H2 / Pd/C View Scheme

2-methyl-3-nitro-6-styrylpyridine (142078-31-7) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) ozonized oxygen, 2.) hydrogen peroxide 2: 100 percent 3: 95 percent / H2 / Pd/C View Scheme

2-methyl-3-pyridinamine (3430-10-2) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether; acetic acid anhydride 2: potassium ethylate / 350 °C View Scheme

2-methyl-3-nitropyridine (18699-87-1) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-methyl-3-pyridinamine (3430-10-2) + 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Stage #1: 2-methyl-3-nitropyridine; N,N-dimethyl-formamide dimethyl acetal In N,N-dimethyl-formamide at 120℃; for 17h; Stage #2: With palladium 10% on activated carbon; hydrogen In methanol; formic acid for 23h;

dimethyl 2-(3-nitropyridin-2-yl)malonate → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 8 h / Reflux 2: N,N-dimethyl-formamide / 4 h / 90 °C / Inert atmosphere 3: formic acid / palladium 10% on activated carbon / methanol / 4 h / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 8 h / Reflux 2: N,N-dimethyl-formamide / 4 h / 90 °C / Inert atmosphere 3: palladium 10% on activated carbon; formic acid / methanol / 4 h / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 8 h / Reflux 2: N,N-dimethyl-formamide / 4 h / 90 °C / Inert atmosphere 3: palladium 10% on activated carbon; formic acid / methanol / 4 h / Inert atmosphere View Scheme

1H-pyrrolo[3,2-b]pyridine (272-49-1) + bromoacetic acid tert-butyl ester (5292-43-3) → tert-butyl 2-(1H-pyrrolo[3,2-b]pyridin-1-yl)acetate

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 1h;	100%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + di-tert-butyl dicarbonate (24424-99-5) → 1H-pyrrolo[3,2-b]pyridine-1-carboxylic acid 1,1-dimethylethyl ester (1018950-15-6)

Conditions	Yield
With dmap In acetonitrile at 20℃; for 3h; Inert atmosphere;	100%
In tetrahydrofuran at 20℃; for 48h;	99%
With dmap; triethylamine In dichloromethane at 20℃;	95%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + (2-bromoethoxy)triethylsilane → 1-(2-(triethylsilyloxy)ethyl)-1H-pyrrolo[3,2-b]pyridine (1018950-17-8)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 1h;	100%

1H-pyrrolo[3,2-b]pyridine (272-49-1) → 1H-pyrrolo[3,2-b]pyridine 4-oxide (1116136-36-7)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 72h;	100%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃;	88%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	70%

1H-pyrrolo[3,2-b]pyridine (272-49-1) → 3-iodo-1H-pyrrolo[3,2-b]pyridine (1083181-26-3)

Conditions	Yield
With N-iodo-succinimide In tetrahydrofuran at 20℃;	100%
With iodine; potassium iodide In ethanol; water at 20℃; for 4h;	98%
With N-iodo-succinimide In tetrahydrofuran at 20℃;	93.5%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + formaldehyd (50-00-0) + N,N-dimethylammonium chloride (506-59-2) → N,N-dimethyl-1-(1H-pyrrolo[3,2-b]pyridin-3-yl)methanamine (23612-34-2)

Conditions	Yield
In butan-1-ol for 3h; Reflux;	99%
In water; butan-1-ol for 3h; Reflux;
In water; butan-1-ol at 120℃; for 3h;

1H-pyrrolo[3,2-b]pyridine (272-49-1) + 1-(3-bromo-2,2-dimethoxypropoxy)-4-octylbenzene → 1-[2,2-dimethoxy-3-(4-octylphenoxy)propyl]-1H-4-azaindole

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate In N,N-dimethyl-formamide for 5h; Reflux;	99%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl 4-(1H-pyrrolo[3,2-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Conditions	Yield
With potassium hydroxide In methanol Heating / reflux;	98%
With potassium hydroxide In methanol Heating;

1H-pyrrolo[3,2-b]pyridine (272-49-1) + 2-mesitylenesulphonyl chloride (773-64-8) → 1-(2,4,6-trimethyl-benzenesulfonyl)-1H-pyrrolo[3,2-b]pyridine (1417718-50-3)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 25℃; for 16h; Inert atmosphere;	96%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 16h;	96%

1H-pyrrolo[3,2-b]pyridine (272-49-1) → C7H5(2)HN2

Conditions	Yield
With water-d2; silver trifluoromethanesulfonate In chloroform-d1 at 90℃; for 18h; regioselective reaction;	95%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + benzenesulfonyl chloride (98-09-9) → 1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine (677302-44-2)

Conditions	Yield
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In tetrahydrofuran Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 20℃;	94%
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil at 20℃; for 4.25h;	57.7%
With triethylamine In tetrahydrofuran

1H-pyrrolo[3,2-b]pyridine (272-49-1) + p-toluenesulfonyl chloride (98-59-9) → 1-tosyl-1H-pyrrolo[3,2-b]pyridine (1116136-30-1)

Conditions	Yield
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 4h;	91%
With dmap; tetra(n-butyl)ammonium hydrogen sulfate; triethylamine In dichloromethane at 20℃; for 26h;	90%
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran at 20℃; for 3.5h;
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.16667h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran for 16h;

1H-pyrrolo[3,2-b]pyridine (272-49-1) + 1,1,1-trifluoroacetophenone (434-45-7) → 2,2,2-trifluoro-1-phenyl-1-(1H-pyrrolo[3,2-b]pyridin-3-yl)ethan-1-ol

Conditions	Yield
With tetrabutyl phosphonium bromide; potassium carbonate In water at 20℃; for 12h; regioselective reaction;	91%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + Benzeneselenol (645-96-5) → 3-(phenylselanyl)-1H-pyrrolo[3,2-b]pyridine

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 27℃; for 2h;	90%

1H-pyrrolo[3,2-b]pyridine (272-49-1) → 3-bromo-1H-pyrrolo[3,2-b]pyridine (23688-47-3)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 0.5h;	89%
With water; sodium bisulfate hydrate; sodium bromide In acetonitrile for 54h; Irradiation;	81%
With sodium hydrogensulfate monohydrate; water; sodium bromide In acetonitrile at 20℃; for 54h; Schlenk technique; Irradiation; Green chemistry;	81%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + hexamethylenetetramine (100-97-0) → 1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde (276862-85-2)

Conditions	Yield
With water; acetic acid for 4h; Reflux;	89%
With water; acetic acid for 6h; Reflux;	79%
With acetic acid In water for 4h; Heating / reflux;	56%
With water; acetic acid Duff Aldehyde Synthesis; Inert atmosphere; Reflux;

1H-pyrrolo[3,2-b]pyridine (272-49-1) → 3-nitro-1H-pyrrolo[3,2-b]pyridine (23612-33-1)

Conditions	Yield
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sulfuric acid; nitric acid at 0℃; for 2h; Stage #2: With sodium hydroxide In water pH=7 - 8;	89%
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sulfuric acid; nitric acid at 0℃; for 2h; Stage #2: With sodium hydroxide In water pH=7 - 8;	89%
With sulfuric acid at 0℃; for 4h;	80%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + m-iodonitrobenzene (645-00-1) → 1-(3-nitrophenyl)-1H-pyrrolo[3,2-c]pyridine

Conditions	Yield
With potassium phosphate; copper In dimethyl sulfoxide at 80℃; for 5h; Inert atmosphere;	89%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + 1-(1-phenylvinyl)tetrahydro-1H-thiophen-1-ium tetraphenylborate → 1-[(E)-styryl]pyrrolo[3,2-b]pyridine

Conditions	Yield
Stage #1: 1H-pyrrolo[3,2-b]pyridine; 1-(1-phenylvinyl)tetrahydro-1H-thiophen-1-ium tetraphenylborate In dimethyl sulfoxide at 21℃; for 0.0333333h; Schlenk technique; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 21℃; for 12h; Schlenk technique; regioselective reaction;	87%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + dihydro-6,7 thieno<3,2-c>pyridine (107112-93-6) → 3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-4-yl)-4-azaindole

Conditions	Yield
In neat (no solvent) at 100℃; for 2h; Temperature; Microwave irradiation;	85%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + N-(2-(4,5-dihydrooxazol-2-yl)-phenyl)-1-methyl-1H-indole-2-carboxamide (1570135-64-6) → N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-1-methyl-3-(1H-pyrrolo[3,2-b]pyridin-1-yl)-1H-indole-2-carboxa mide

Conditions	Yield
With potassium acetate; copper diacetate at 80℃; for 12h; Schlenk technique; Sealed tube;	85%
With copper diacetate; sodium carbonate In dimethyl sulfoxide at 80℃; for 2h; Sealed tube;	85%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + methyl iodide (74-88-4) → 1-methyl-1H-pyrrolo[3,2-b]pyridine (153374-33-5)

Conditions	Yield
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 5℃; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	84.5%
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere;	83%
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: methyl iodide In tetrahydrofuran for 24h;	31%
In N,N-dimethyl-formamide
Stage #1: 1H-pyrrolo[3,2-b]pyridine With Tris(3,6-dioxaheptyl)amine; potassium tert-butylate In toluene at 20℃; for 5h; Stage #2: methyl iodide In toluene at 20℃; for 24h;

1H-pyrrolo[3,2-b]pyridine (272-49-1) + cyclohexanedione monoethylene ketal (4746-97-8) → 3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1H-pyrrolo[3,2-b]pyridine (1209481-93-5)

Conditions	Yield
With potassium hydroxide In methanol Reflux; Inert atmosphere; Schlenk technique;	84%
With potassium hydroxide In methanol for 4h; Reflux;

1H-pyrrolo[3,2-b]pyridine (272-49-1) + allyl bromide (106-95-6) → 1-allyl-3-bromo-1H-pyrrolo[3,2-b]pyridine

Conditions	Yield
With tetrabutylammomium bromide; sodium bromide In acetonitrile at 20℃; for 2h; Electrolysis; Inert atmosphere; Green chemistry;	84%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + benzenesulfonyl chloride (98-09-9) → 1-benzenesulfonyl-1H-pyrrolo [3, 2-b] pyridine

Conditions	Yield
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In dimethyl sulfoxide for 0.25h; Stage #2: benzenesulfonyl chloride for 0.5h;	83%

Upstream product

• 116286-64-7 N-(2-methyl-[3]pyridyl)-formamide 
• 917-58-8 potassium ethoxide 
• 65156-92-5 2-(3-nitro-2-pyridinyl)-N,N-dimethyletheneamine 
• 107479-62-9 2-(2,2-diethoxyethyl)-3-nitropyridine 
• 123846-65-1 2-(3-nitropyridin-2-yl)acetonitrile 
• 173417-34-0 dimethyl 2-(3-nitropyridin-2-yl)malonate 
• 150281-83-7 2-ethenyl-3-nitropyridine 
• 24509-73-7 1-(1H-pyrrolo[3,2-b]pyridin-1-yl)ethanone 
• 18699-87-1 2-methyl-3-nitropyridine 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 849353-49-7 (2-trimethylsilanylethynylpyridin-3-yl) carbamic acid tert-butyl ester 
• 3430-10-2 2-methyl-3-pyridinamine 
• 142078-31-7 2-methyl-3-nitro-6-styrylpyridine 
• 15513-52-7 3-nitro-2,6-lutidine 

Downstream Products

• 153374-33-5 1-methyl-1H-pyrrolo[3,2-b]pyridine 
• 1165803-46-2 C₁₄H₉N₃O₃ 
• 1165803-16-6 C₁₃H₈Cl₂N₂O₂S 
• 1165803-47-3 C₁₅H₁₃N₃O₂ 
• 1165803-20-2 C₁₄H₁₂N₂O₃S 
• 1165803-22-4 C₁₄H₁₂N₂O₄S₂ 
• 1165803-15-5 C₁₃H₈Cl₂N₂O₂S 
• 1165803-12-2 C₁₃H₉ClN₂O₂S 
• 1165803-18-8 C₁₃H₉N₃O₄S 
• 677302-44-2 1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine 
• 1165803-17-7 C₁₃H₉N₃O₄S 
• 1165803-19-9 C₁₃H₉N₃O₄S 
• 1165803-14-4 C₁₃H₈Cl₂N₂O₂S 
• 1165803-13-3 C₁₃H₉ClN₂O₂S 

Relevant articles and documents

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