875781-43-4

Basic information

• Product Name: 5-Bromo-4,7-diazaindole
• Synonyms: 5-BROMO-4,7-DIAZAINDOLE;2-Bromo-5H-pyrrolo[2,3-b]pyrazine;5H-Pyrrolo[2,3-b]pyrazine, 2-bromo-;2-broMo-5H-pyrrolo[2,3-b]pyrazine 2-broMo-5H-pyrrolo[3,2-b]pyrazine;4H-Pyrrolo[2,3-b]pyrazine, 2-bromo-
• CAS NO: 875781-43-4
• Molecular Formula: C₆H₄BrN₃
• Molecular Weight: 198.02
• EINECS: 1308068-626-2
• Product Categories: upadacitinib
• Mol File: 875781-43-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 265 °C
• Flash Point: 114 °C
• Appearance: /
• Density: 2.00
• Refractive Index: 1.746
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 10.58±0.50(Predicted)
• CAS DataBase Reference: 5-Bromo-4,7-diazaindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-4,7-diazaindole(875781-43-4)
• EPA Substance Registry System: 5-Bromo-4,7-diazaindole(875781-43-4)

Safety Data

• Hazardous Substances Data: 875781-43-4(Hazardous Substances Data)

Usage

General Description

5-Bromo-4,7-diazaindole is a chemical compound with the molecular formula C8H6BrN3. It is a heterocyclic compound containing a diazaindole ring system with a bromine substituent at the 5-position. 5-Bromo-4,7-diazaindole is commonly used in organic synthesis and medicinal chemistry as a building block for the synthesis of novel drug molecules and biologically active compounds. It has been studied for its potential as a pharmaceutical intermediate and has shown promising biological activities, making it a valuable tool for drug discovery and development. Additionally, 5-Bromo-4,7-diazaindole has been investigated for its potential use in the synthesis of fluorescent dyes and materials for various applications in chemical and materials science.

InChI:InChI=1/C6H4BrN3/c7-5-3-9-6-4(10-5)1-2-8-6/h1-3H,(H,8,9)

Synthetic route

5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine (875781-41-2) → 2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Reflux;	76%
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one for 3h; Heating;	69%
Multi-step reaction with 2 steps 1: pyridine / tetrahydrofuran / 96 h 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h / 75 °C View Scheme

5-bromo-3-(2-triethylsilylethynyl)pyrazin-2-amine (1416740-15-2) → 2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4)

Conditions	Yield
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 80℃; for 1.5h;	70.3%

N-(5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-yl)acetamide (875781-42-3) → 2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 15h;	43%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 75℃; for 20h;	42%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 75℃; for 20h;	42%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 75℃; for 20h;	42%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 15h; Reflux;	16%

C10H13BrN4O → 2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4)

Conditions	Yield
In water for 0.5h;	91 g

C10H15BrN4 → 2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4)

Conditions	Yield
In water for 0.5h;	90 g

C14H23BrN4 → 2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4)

Conditions	Yield
In water for 0.5h;	90.2 g

5-bromo-3-ethynyl-pyrazin-2-ylamine (1209289-08-6) → 2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 60 °C 2: water / 0.5 h View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 60 °C 2: water / 0.5 h View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 60 °C 2: water / 0.5 h View Scheme

C11H16BrN5 → 2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4)

Conditions	Yield
In water for 0.5h; Solvent;	9.3 kg

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) → 2-bromo-7-iodo-5H-pyrrolo[2,3-b]pyrazine (875781-44-5)

Conditions	Yield
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 1h;	100%
With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;	95%
With N-iodo-succinimide In acetone at 20℃; for 4h;	89%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + p-toluenesulfonyl chloride (98-59-9) → 2-bromo-7-iodo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (875781-45-6)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 3.33333h;	99%

formaldehyd (50-00-0) + 2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) → (2-bromo-5-hydroxymethyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-methanol (1334674-87-1)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane at 20℃; Inert atmosphere;	99%
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 18h;	95.5%
Stage #1: formaldehyd; 2-bromo-5H-pyrrolo[2,3-b]pyrazine With sodium hydroxide In 1,4-dioxane; water at 20℃; Stage #2: With hydrogenchloride In water	87%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + p-toluenesulfonyl chloride (98-59-9) → 2-bromo-5-(p-toluenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine (1201186-54-0)

Conditions	Yield
Stage #1: 2-bromo-5H-pyrrolo[2,3-b]pyrazine With sodium hydride In N,N-dimethyl-formamide at 0 - 5℃; for 0.5h; Stage #2: p-toluenesulfonyl chloride In N,N-dimethyl-formamide at 0 - 20℃;	97%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 30℃; for 8h; Inert atmosphere;	86%
With sodium hydride In tetrahydrofuran; mineral oil at -15 - 20℃; for 1h;	79.3%
With triethylamine In dichloromethane at 20℃; for 3h; Solvent; Reagent/catalyst; Temperature;	56.1%
With sodium hydride In N,N-dimethyl-formamide

4-(isopropylsulfonyl)phenylboronic acid + 2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) → 2-(4-(isopropylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazine (1353571-87-5)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃;	95%

4-tert-butylbenzenesulfonyl chloride (15084-51-2) + 2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) → 2-bromo-5-(4-tert-butylphenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine (1201186-50-6)

Conditions	Yield
Stage #1: 2-bromo-5H-pyrrolo[2,3-b]pyrazine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: 4-tert-butylbenzenesulfonyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 10℃; for 2h;	91%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine (1184926-29-1)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;	90%
Stage #1: 2-bromo-5H-pyrrolo[2,3-b]pyrazine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3h;	90%
Stage #1: 2-bromo-5H-pyrrolo[2,3-b]pyrazine With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide Stage #3: With water In N,N-dimethyl-formamide Product distribution / selectivity;	86%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + benzenesulfonyl chloride (98-09-9) → 5-(benzenesulfonyl)-2-bromo-5H-pyrrolo[2,3-b]pyrazine

Conditions	Yield
Stage #1: 2-bromo-5H-pyrrolo[2,3-b]pyrazine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil for 1h;	88%
Stage #1: 2-bromo-5H-pyrrolo[2,3-b]pyrazine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil at 20℃; for 12h;	82%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + methyl 3-ethynyl 4-methylbenzoate → C17H13N3O2

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl acetamide at 50 - 80℃; for 24h; Solvent; Inert atmosphere;	88%

formaldehyd (50-00-0) + 2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) → (2-bromo-7-hydroxymethylpyrrolo[2,3-b]pyrazin-5-yl)methanol

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water	87%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + 3,4,5-trimethoxyphenylboronic Acid (182163-96-8) → 2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine (1422772-45-9)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 110℃; for 18h;	83%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + 4-(3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole → 2-[2-methoxy-4-(1-tetrahydropyran-2-ylpyrazol-4-yl)phenyl]-5H-pyrrolo[2,3-b]pyrazine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane at 90℃; for 16h; Suzuki Coupling; Inert atmosphere;	80%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + 3,4-Dimethoxyphenylboronic acid (122775-35-3) → 2-(3,4-dimethoxyphenyl)-5H-pyrrolo[2,3-b]pyrazine (1422772-49-3)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 110℃; for 18h;	76.9%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + (2-fluoro-pyridin-3-yl)boronic acid (174669-73-9) → 2-(2-fluoropyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazine (1270497-00-1)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; ethanol; water at 140℃; for 0.25h; Inert atmosphere; microwave irradiation; sealed tube;	76%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole (832114-00-8) → 3,5-dimethyl-4-(5H-pyrrolo[2,3-b]pyrazin-2-yl)isoxazole

Conditions	Yield
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate In water; acetonitrile at 160℃; for 0.333333h; Microwave irradiation;	76%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + methyl iodide (74-88-4) → 2-bromo-5-methyl-5H-pyrrolo[2,3-b]pyrazine

Conditions	Yield
Stage #1: 2-bromo-5H-pyrrolo[2,3-b]pyrazine With sodium hydride In tetrahydrofuran at 0 - 18℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran at 18℃; for 2h;	72%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + pivaloyl chloride (3282-30-2) → 1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one (1184852-23-0)

Conditions	Yield
Stage #1: 2-bromo-5H-pyrrolo[2,3-b]pyrazine With diethylaluminium chloride In hexane; dichloromethane at 0 - 5℃; for 0.5h; Stage #2: pivaloyl chloride In hexane; dichloromethane for 15h; Reflux;	63%
Stage #1: 2-bromo-5H-pyrrolo[2,3-b]pyrazine With diethyl aluminiumcholoride In hexane; dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: pivaloyl chloride at 0 - 20℃; for 21.1667h;

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + 4-pyridylboronic acid (1692-15-5) → 2-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine (1604036-45-4)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In water; acetonitrile at 150℃; for 0.5h; Microwave irradiation;	60%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In acetonitrile at 150℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Microwave irradiation;	0.28 g

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) → 2-chloro-5H-pyrrolo[2,3-b]pyrazine (889447-19-2)

Conditions	Yield
With triethylamine; trichlorophosphate In 1,4-dioxane at 110℃; for 6h;	54%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + trityl chloride (76-83-5) → 2-bromo-5-trityl-5H-pyrrolo[2,3-b]pyrazine

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 40℃; for 2h;	52%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + isopropylamine (75-31-0) → 2-bromo-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide

Conditions	Yield
Stage #1: 2-bromo-5H-pyrrolo[2,3-b]pyrazine With chlorosulfonic acid at 0 - 120℃; for 2.5h; Inert atmosphere; Stage #2: isopropylamine With triethylamine In dichloromethane at 0℃; for 3h; Inert atmosphere;	49%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + 1-methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine (747413-21-4) → 2-(4-(4-methylpiperazin-1-yl)phenyl)-5H-pyrrolo[2,3-b]pyrazine

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 100℃; for 16h; Sealed tube; Inert atmosphere;	40.5%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + hexamethylenetetramine (100-97-0) → 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (1185428-32-3)

Conditions	Yield
With trifluoroacetic acid at 0 - 110℃; for 12h;	40%
With trifluoroacetic acid at 80℃; for 0.25h; Microwave irradiation;	0.45 g

(4-bromo-2-fluorophenyl)boronic acid + 2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) → 2-(4-bromo-2-fluorophenyl)-5H-pyrrolo[2,3-b]pyrazine

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 95℃; for 24h; Inert atmosphere;	35%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + 4-nitrobenzaldehdye (555-16-8) → (2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)(4-nitrophenyl)methanol

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 48h;	25.3%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + 2-[(1S)-1-cyclopropylethyl]-7-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-isoindol-1-one → 2-[(1S)-1-cyclopropylethyl]-7-methyl-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-2,3-dihydro-1H-isoindol-1-one

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 140℃; for 0.5h; Suzuki Coupling; Inert atmosphere; Sealed tube; Microwave irradiation;	10%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + 4-Chlorophenylboronic acid (1679-18-1) → 2-(4-chloro-phenyl)-5H-pyrrolo[2,3-b]pyrazine

Conditions	Yield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; acetonitrile at 120℃; for 0.166667h; Suzuki Coupling; Microwave irradiation;

Upstream product

• 875781-42-3 N-(5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-yl)acetamide 
• 875781-41-2 5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine 
• 1416740-15-2 5-bromo-3-(2-triethylsilylethynyl)pyrazin-2-amine 
• 1209289-08-6 5-bromo-3-ethynyl-pyrazin-2-ylamine 

Downstream Products

• 875781-44-5 2-bromo-7-iodo-5H-pyrrolo[3,2-b]pyrazine 
• 1201186-54-0 2-bromo-5-(p-toluenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine 
• 1201186-50-6 2-bromo-5-(4-tert-butylphenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine 
• 1150617-58-5 2-bromo-7-chloro-5H-pyrrolo[2,3-b]pyrazine 
• 1350473-38-9 2-cyclopropyl-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyclohexylamide 
• 1350473-40-3 N-(1-benzyl-4,4-dimethylpiperidin-3-yl)-2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide 
• 1350473-45-8 2-cyclopropyl-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-cyanophenyl)amide 
• 1350473-56-1 2-phenoxy-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyclohexylamide 
• 1350473-04-9 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyclohexylamide 
• 1350473-24-3 2-phenoxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyclohexylamide 
• 1350473-14-1 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-cyanophenyl)amide 
• 1350712-62-7 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyclohexylmethyl-amide 
• 1350712-69-4 2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-cyclopropyl-ethyl)-amide 
• 1350708-05-2 2-phenoxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-cyclopropyl-ethyl)-amide 

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