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5-Bromo-4,7-diazaindole is a heterocyclic chemical compound with the molecular formula C8H6BrN3. It features a diazaindole ring system, which is a fused ring structure containing two nitrogen atoms, with a bromine substituent at the 5-position. 5-Bromo-4,7-diazaindole is widely utilized in organic synthesis and medicinal chemistry as a versatile building block for the creation of novel drug molecules and biologically active compounds. Its potential as a pharmaceutical intermediate and its demonstrated biological activities make 5-Bromo-4,7-diazaindole a valuable asset in drug discovery and development processes. Furthermore, it has been explored for its application in the synthesis of fluorescent dyes and materials, broadening its relevance in chemical and materials science.

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  • 5-Bromo-4,7-diazaindole 875781-43-4 Factory PRICE IN STOCK COA CAS 875781-43-4

    Cas No: 875781-43-4

  • USD $ 3.5-5.0 / Kiloliter

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  • 875781-43-4 Structure
  • Basic information

    1. Product Name: 5-Bromo-4,7-diazaindole
    2. 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-
    3. CAS NO:875781-43-4
    4. Molecular Formula: C6H4BrN3
    5. Molecular Weight: 198.02
    6. EINECS: 1308068-626-2
    7. Product Categories: upadacitinib
    8. Mol File: 875781-43-4.mol
  • Chemical Properties

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

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 875781-43-4(Hazardous Substances Data)

875781-43-4 Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-4,7-diazaindole is used as a pharmaceutical intermediate for the synthesis of novel drug molecules and biologically active compounds. Its unique structure and properties make it a promising candidate for the development of new therapeutic agents.
Used in Medicinal Chemistry:
In medicinal chemistry, 5-Bromo-4,7-diazaindole is employed as a building block for the design and synthesis of new compounds with potential therapeutic applications. Its ability to be modified and incorporated into various molecular frameworks contributes to the discovery of innovative drugs.
Used in Chemical Science:
5-Bromo-4,7-diazaindole is used in the synthesis of fluorescent dyes and materials. Its incorporation into these compounds allows for the development of new tools and technologies in chemical analysis, imaging, and sensing applications.
Used in Materials Science:
In materials science, 5-Bromo-4,7-diazaindole is utilized for the development of new materials with specific properties, such as fluorescence, which can be applied in various fields including optoelectronics, sensors, and bioimaging.

Check Digit Verification of cas no

The CAS Registry Mumber 875781-43-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,7,5,7,8 and 1 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 875781-43:
(8*8)+(7*7)+(6*5)+(5*7)+(4*8)+(3*1)+(2*4)+(1*3)=224
224 % 10 = 4
So 875781-43-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H4BrN3/c7-5-3-9-6-4(10-5)1-2-8-6/h1-3H,(H,8,9)

875781-43-4Synthetic route

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

5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine

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

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

Conditions
ConditionsYield
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

5-bromo-3-(2-triethylsilylethynyl)pyrazin-2-amine

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

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

Conditions
ConditionsYield
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

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

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

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

Conditions
ConditionsYield
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

C10H13BrN4O

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

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

Conditions
ConditionsYield
In water for 0.5h;91 g
C10H15BrN4

C10H15BrN4

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

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

Conditions
ConditionsYield
In water for 0.5h;90 g
C14H23BrN4

C14H23BrN4

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

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

Conditions
ConditionsYield
In water for 0.5h;90.2 g
5-bromo-3-ethynyl-pyrazin-2-ylamine
1209289-08-6

5-bromo-3-ethynyl-pyrazin-2-ylamine

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

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

Conditions
ConditionsYield
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

C11H16BrN5

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

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

Conditions
ConditionsYield
In water for 0.5h; Solvent;9.3 kg
2-bromo-5H-pyrrolo[2,3-b]pyrazine
875781-43-4

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

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

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

Conditions
ConditionsYield
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

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

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

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

2-bromo-7-iodo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 3.33333h;99%
formaldehyd
50-00-0

formaldehyd

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

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

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

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

Conditions
ConditionsYield
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

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

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

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

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

Conditions
ConditionsYield
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

4-(isopropylsulfonyl)phenylboronic acid

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

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

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

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

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃;95%
4-tert-butylbenzenesulfonyl chloride
15084-51-2

4-tert-butylbenzenesulfonyl chloride

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

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

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

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

Conditions
ConditionsYield
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-bromo-5H-pyrrolo[2,3-b]pyrazine

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

(2-trimethylethylsilylethoxy)methyl chloride

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

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

Conditions
ConditionsYield
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

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

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

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

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

Conditions
ConditionsYield
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

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

methyl 3-ethynyl 4-methylbenzoate

methyl 3-ethynyl 4-methylbenzoate

C17H13N3O2

C17H13N3O2

Conditions
ConditionsYield
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

formaldehyd

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

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

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

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

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water87%
2-bromo-5H-pyrrolo[2,3-b]pyrazine
875781-43-4

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

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

3,4,5-trimethoxyphenylboronic Acid

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

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

Conditions
ConditionsYield
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

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

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

2-[2-methoxy-4-(1-tetrahydropyran-2-ylpyrazol-4-yl)phenyl]-5H-pyrrolo[2,3-b]pyrazine

Conditions
ConditionsYield
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

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

3,4-Dimethoxyphenylboronic acid
122775-35-3

3,4-Dimethoxyphenylboronic acid

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

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

Conditions
ConditionsYield
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-bromo-5H-pyrrolo[2,3-b]pyrazine

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

(2-fluoro-pyridin-3-yl)boronic acid

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

2-(2-fluoropyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazine

Conditions
ConditionsYield
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

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

3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole
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

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

Conditions
ConditionsYield
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

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

methyl iodide
74-88-4

methyl iodide

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

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

Conditions
ConditionsYield
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

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

pivaloyl chloride
3282-30-2

pivaloyl chloride

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

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

Conditions
ConditionsYield
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

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

4-pyridylboronic acid
1692-15-5

4-pyridylboronic acid

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

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

Conditions
ConditionsYield
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-bromo-5H-pyrrolo[2,3-b]pyrazine

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

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

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In 1,4-dioxane at 110℃; for 6h;54%
2-bromo-5H-pyrrolo[2,3-b]pyrazine
875781-43-4

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

trityl chloride
76-83-5

trityl chloride

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

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

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 40℃; for 2h;52%
2-bromo-5H-pyrrolo[2,3-b]pyrazine
875781-43-4

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

isopropylamine
75-31-0

isopropylamine

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

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

Conditions
ConditionsYield
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

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

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

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

Conditions
ConditionsYield
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

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

hexamethylenetetramine
100-97-0

hexamethylenetetramine

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

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

Conditions
ConditionsYield
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

(4-bromo-2-fluorophenyl)boronic acid

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

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

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

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

Conditions
ConditionsYield
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

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

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

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

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

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 48h;25.3%
2-bromo-5H-pyrrolo[2,3-b]pyrazine
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-(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

2-[(1S)-1-cyclopropylethyl]-7-methyl-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-2,3-dihydro-1H-isoindol-1-one

Conditions
ConditionsYield
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

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

4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

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

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

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

875781-43-4Downstream Products

875781-43-4Relevant articles and documents

Synthetic method of indole or azabenzopyrrole compound

-

Paragraph 0087; 0095-0097; 0098-0099, (2021/03/31)

The invention relates to a synthetic method of an indole or azabenzopyrrole compound. The synthetic method comprises the following steps: carrying out cyclization reaction on a compound A and disubstituted amine in a solvent, wherein the structural general formula of the disubstituted amine is NH(R2)2, R2 is respectively and independently selected from C1-C6 alkyl, C1-C6 alkyl hydroxyl, C1-C6 alkyl O-C1-C6 alkyl, C1-C6 alkyl NH-C1-C6 alkyl or C1-C6 alkylamino, and the two R2 are connected with each other to form a ring or not form a ring. According to the synthetic method of the indole or azabenzopyrrole compound, the disubstituted amine compound with a specific structural general formula and the terminal alkynyl of the intermediate are subjected to an addition reaction, the rigid structure of the terminal alkynyl is changed, and the structure of alkenyl amine is changed, so that under mild reaction conditions, ring closing of pyrrole groups in indole or azabenzopyrrole compounds is realized, side reactions are few, the product yield is high, and the production cost of the product is reduced from the source.

Synthesis and Structure-Activity Relationships of 3,5-Disubstituted-pyrrolo[2,3- b]pyridines as Inhibitors of Adaptor-Associated Kinase 1 with Antiviral Activity

Verdonck, Sven,Pu, Szu-Yuan,Sorrell, Fiona J.,Elkins, Jon M.,Froeyen, Mathy,Gao, Ling-Jie,Prugar, Laura I.,Dorosky, Danielle E.,Brannan, Jennifer M.,Barouch-Bentov, Rina,Knapp, Stefan,Dye, John M.,Herdewijn, Piet,Einav, Shirit,De Jonghe, Steven

, p. 5810 - 5831 (2019/07/04)

There are currently no approved drugs for the treatment of emerging viral infections, such as dengue and Ebola. Adaptor-associated kinase 1 (AAK1) is a cellular serine-threonine protein kinase that functions as a key regulator of the clathrin-associated host adaptor proteins and regulates the intracellular trafficking of multiple unrelated RNA viruses. Moreover, AAK1 is overexpressed specifically in dengue virus-infected but not bystander cells. Because AAK1 is a promising antiviral drug target, we have embarked on an optimization campaign of a previously identified 7-azaindole analogue, yielding novel pyrrolo[2,3-b]pyridines with high AAK1 affinity. The optimized compounds demonstrate improved activity against dengue virus both in vitro and in human primary dendritic cells and the unrelated Ebola virus. These findings demonstrate that targeting cellular AAK1 may represent a promising broad-spectrum antiviral strategy.

Heteroaromatic compound and application thereof to drug

-

Paragraph 0543; 0544; 0545, (2017/07/31)

The invention discloses a heteroaromatic compound and application thereof to drug. In particular, the invention provides a heteroaromatic compound or stereoisomers thereof, geometric isomers, tautomers, racemates, nitrogen oxides, hydrates, solvates, metabolites, pharmaceutically acceptable salts or prodrugs thereof, and a pharmaceutical composition comprising the compound provided by the invention. The invention also discloses application of the compound provided by the invention or the pharmaceutical composition thereofto preparation of a medicine for reatment of autoimmune diseases or proliferative diseases.

AZAINDOLE DERIVATIVES AS JAK3 INHIBITORS

-

Page/Page column 32, (2014/06/11)

The present disclosure provides compounds that are JAK3 inhibitors and therefore useful for the treatment of diseases treatable by inhibition of JAK3 such as cancer and inflammatory diseases. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

MIXED LINEAGE KINASE INHIBITORS FOR HIV/AIDS THERAPIES

-

, (2014/06/23)

Disclosed are methods for treating an individual infected with a retrovirus that comprise administering to the individual effective amounts of a mixed lineage kinase inhibitor and antiretroviral drug. In further aspects, disclosed are methods for treating an individual infected with a retrovirus that comprises administering an antiretroviral drug formulated into a crystalline nanoparticle comprising a surfactant, and a MLK inhibitor. Still further disclosed are methods for treating an individual infected with a retrovirus that comprises administering a composition comprising both an antiretroviral and MLK inhibitor formulated into a crystalline nanoparticle, which comprises a surfactant. Still further disclosed are compositions that comprise an antiretroviral drug, a MLK inhibitor, and a surfactant, wherein the composition is a crystalline nanoparticle. Compostions comprising MLK inhibitors with other drugs in nanoparticulate form, and methods of there use, are also disclosed.

COMPOUNDS USEFUL AS INHIBITORS OF ATR KINASE

-

Page/Page column 63-64, (2013/02/28)

The present invention relates to pyrrolopyrazines compounds useful as inhibitors of ATR protein kinase. The invention also relates to pharmaceutically acceptable compositions comprising the compounds of this invention; methods of treating of various diseases, disorders, and conditions using the compounds of this invention; processes for preparing the compounds of this invention; intermediates for the preparation of the compounds of this invention; and methods of using the compounds in in vitro applications, such as the study of kinases in biological and pathological phenomena; the study of intracellular signal transduction pathways mediated by such kinases; and the comparative evaluation of new kinase inhibitors. The compounds of this invention have formula I wherein the variables are as defined herein

AZAINDOLE DERIVATIVES AS TYROSINE KINASE INHIBITORS

-

Page/Page column 90, (2012/12/13)

The present disclosure provides compounds and pharmaceutically acceptable salts that are tyrosine kinase inhibitors, in particular BLK, BMX, EGFR, HER2, HER4, ITK, JAK3, TEC, Btk, and TXK and are therefore useful for the treatment of diseases treatable by inhibition of tyrosine kinases such as cancer and inflammatory diseases such as arthritis, and the like. Also provided are pharmaceutical compositions containing such compounds and pharmaceutically acceptable salts and processes for preparing such compounds and pharmaceutically acceptable salts.

BICYCLIC HETEROARYL KINASE INHIBITORS AND METHODS OF USE

-

, (2011/12/14)

Provided are compounds having an inhibitory effect on kinases including Mixed Lineage Kinases. Also provided are pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions that are affected by Mixed Lineage Kinase inhibition. Also provided are methods of treatment of neuropsychiatric disorders that comprise the inhibition of Mixed Lineage Kinases.

MLK INHIBITORS AND METHODS OF USE

-

Page/Page column 67-68, (2010/07/02)

Provided are compounds having an inhibitory effect on Mixed Lineage Kinases. Also provided are pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions which are affected by Mixed Lineage Kinase inhibition. Also provided are methods of treatment of neuropsychiatric disorders which comprise the inhibition of Mixed Lineage Kinases.

HISTAMINE H3 INVERSE AGONISTS AND ANTAGONISTS AND METHODS OF USE THEREOF

-

Page/Page column 114-115, (2010/08/18)

Provided herein are fused imidazolyl compounds, methods of synthesis, and methods of use thereof. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders and metabolic disorders. Compounds provided herein inhibit the activity of histamine H3 receptors and modulate the release of various neurotransmitters, such as histamine, acetylcholine, norepinephrine, and dopamine (e.g. at the synapse). Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.

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