5-Bromo-4,7-diazaindole supplier

Name
5-Bromo-4,7-diazaindole
EINECS 1308068-626-2
CAS No. 875781-43-4
Article Data11
CAS DataBase
Density 1.895 g/cm³
Solubility
Melting Point
Formula C₆H₄BrN₃
Boiling Point 265 °C
Molecular Weight 198.022
Flash Point 114 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4H-Pyrrolo[2,3-b]pyrazine,2-bromo- (9CI);2-Bromo-5H-pyrrolo[2,3-b]pyrazine;
PSA 41.57000
LogP 1.72040

Synthetic route

: 875781-41-2
5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

Conditions

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

: 1416740-15-2
5-bromo-3-(2-triethylsilylethynyl)pyrazin-2-amine

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

Conditions

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

: 875781-42-3
N-(5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-yl)acetamide

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

Conditions

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

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

Conditions

Conditions	Yield
In water for 0.5h;	91 g

: C10H15BrN4

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

Conditions

Conditions	Yield
In water for 0.5h;	90 g

: C14H23BrN4

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

Conditions

Conditions	Yield
In water for 0.5h;	90.2 g

: 1209289-08-6
5-bromo-3-ethynyl-pyrazin-2-ylamine

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

Conditions

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

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

Conditions

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

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 875781-44-5
2-bromo-7-iodo-5H-pyrrolo[2,3-b]pyrazine

Conditions

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%

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 98-59-9
p-toluenesulfonyl chloride

: 875781-45-6
2-bromo-7-iodo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

Conditions

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

: 50-00-0
formaldehyd

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 1334674-87-1
(2-bromo-5-hydroxymethyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-methanol

Conditions

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%

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 98-59-9
p-toluenesulfonyl chloride

: 1201186-54-0
2-bromo-5-(p-toluenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine

Conditions

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

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 1353571-87-5
2-(4-(isopropylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazine

Conditions

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

: 15084-51-2
4-tert-butylbenzenesulfonyl chloride

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 1201186-50-6
2-bromo-5-(4-tert-butylphenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine

Conditions

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%

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

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

: 1184926-29-1
2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine

Conditions

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%

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 98-09-9
benzenesulfonyl chloride

: 5-(benzenesulfonyl)-2-bromo-5H-pyrrolo[2,3-b]pyrazine

Conditions

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%

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: methyl 3-ethynyl 4-methylbenzoate

: C17H13N3O2

Conditions

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%

: 50-00-0
formaldehyd

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: (2-bromo-7-hydroxymethylpyrrolo[2,3-b]pyrazin-5-yl)methanol

Conditions

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

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 182163-96-8
3,4,5-trimethoxyphenylboronic Acid

: 1422772-45-9
2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

Conditions

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

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 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

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%

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 122775-35-3
3,4-Dimethoxyphenylboronic acid

: 1422772-49-3
2-(3,4-dimethoxyphenyl)-5H-pyrrolo[2,3-b]pyrazine

Conditions

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%

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 174669-73-9
(2-fluoro-pyridin-3-yl)boronic acid

: 1270497-00-1
2-(2-fluoropyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazine

Conditions

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%

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 832114-00-8
3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole

: 3,5-dimethyl-4-(5H-pyrrolo[2,3-b]pyrazin-2-yl)isoxazole

Conditions

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

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 74-88-4
methyl iodide

: 2-bromo-5-methyl-5H-pyrrolo[2,3-b]pyrazine

Conditions

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%

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 3282-30-2
pivaloyl chloride

: 1184852-23-0
1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

Conditions

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;

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 1692-15-5
4-pyridylboronic acid

: 1604036-45-4
2-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine

Conditions

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

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 889447-19-2
2-chloro-5H-pyrrolo[2,3-b]pyrazine

Conditions

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

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 76-83-5
trityl chloride

: 2-bromo-5-trityl-5H-pyrrolo[2,3-b]pyrazine

Conditions

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

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 75-31-0
isopropylamine

: 2-bromo-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide

Conditions

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%

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 747413-21-4
1-methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine

: 2-(4-(4-methylpiperazin-1-yl)phenyl)-5H-pyrrolo[2,3-b]pyrazine

Conditions

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%

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 100-97-0
hexamethylenetetramine

: 1185428-32-3
2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

Conditions

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

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 2-(4-bromo-2-fluorophenyl)-5H-pyrrolo[2,3-b]pyrazine

Conditions

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%

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 555-16-8
4-nitrobenzaldehdye

: (2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)(4-nitrophenyl)methanol

Conditions

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

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 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

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%

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 1679-18-1
4-Chlorophenylboronic acid

: 2-(4-chloro-phenyl)-5H-pyrrolo[2,3-b]pyrazine

Conditions

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;

5-Bromo-4,7-diazaindole Chemical Properties

IUPAC Name: 2-Bromo-5H-pyrrolo[2,3-b]pyrazine
Synonyms of 5-Bromo-4,7-diazaindole (CAS NO.875781-43-4): 2-Bromo-5H-pyrrolo[2,3-b]pyrazine ; 5H-Pyrrolo[2,3-b]pyrazine,2-bromo-
CAS NO: 875781-43-4
Molecular Formula: C₆H₄BrN₃
Molecular Weight: 198.02
Molecular Structure:
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 0
Polar Surface Area: 41.57 Å²
Index of Refraction: 1.745
Molar Refractivity: 42.4 cm³
Molar Volume: 104.5 cm³
Surface Tension: 76.9 dyne/cm
Density: 1.894 g/cm³
SMILES: Brc1cnc2nccc2n1
InChI: InChI=1/C6H4BrN3/c7-5-3-9-6-4(10-5)1-2-8-6/h1-3H,(H,8,9)
InChIKey: KTKMLXBEBKGQGL-UHFFFAOYAB
Std. InChI: InChI=1S/C6H4BrN3/c7-5-3-9-6-4(10-5)1-2-8-6/h1-3H,(H,8,9)
Std. InChIKey: KTKMLXBEBKGQGL-UHFFFAOYSA-N

Product Name

5-Bromo-4,7-diazaindole

Synthetic route

5-Bromo-4,7-diazaindole Chemical Properties

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