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ChemicalBook > Product Catalog >Pharmaceutical intermediates >Heterocyclic compound >N-Tosyl-5-bromo-4,7-diazaindole

N-Tosyl-5-bromo-4,7-diazaindole

N-Tosyl-5-bromo-4,7-diazaindole Structure
CAS No.
1201186-54-0
Chemical Name:
N-Tosyl-5-bromo-4,7-diazaindole
Synonyms
2-BroMo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine;5H-Pyrrolo[2,3-b]pyrazine, 2-bromo-5-[(4-methylphenyl)sulfonyl]-;Upatinib Impurity 2;Upatinib Impurity 45;Upadacitinib Impurity 2;Upadacitinib Impurity 45;N-Tosyl-5-bromo-4,7-diazaindole;Glycerol(Glycerophosphoric acid);3-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine;2-BROMO-5-(P-TOLYLSULFONYL)-5H-PYRROLO[2,3-B]PYRAZINE
CBNumber:
CB62470216
Molecular Formula:
C13H10BrN3O2S
Molecular Weight:
352.21
MOL File:
1201186-54-0.mol
MSDS File:
SDS
Modify Date:
2024/4/7 18:44:46
Request For Quotation

N-Tosyl-5-bromo-4,7-diazaindole Properties

Boiling point 499.6±55.0 °C(Predicted)
Density 1.68±0.1 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka -2.22±0.30(Predicted)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338

N-Tosyl-5-bromo-4,7-diazaindole Chemical Properties,Uses,Production

Uses

N-Tosyl-5-bromo-4,7-diazaindole is an intermediate of upadacitinib, known asupadacitinib intermediate, or upadacitinib impurity 2. As an inhibitor of Janus kinase1, upadacitinib selectively inhibits Janus kinase1 for immune system diseases such as psoriatic arthritis, rheumatoid arthritis, and Crohn's disease[1-3].

Preparation

A solution of anhydrous DMF (272 mL) dissolved with 2-bromo-5H-pyrrolo[2,3-b]pyrazine (78.0 g, 394 mmol) was configured. The temperature is maintained at 0-5 °C (within which the subsequent reaction has been maintained), and the solution was droppedly added to the sodium (12.8 g, 532 mmol) anhydrous DMF (543 mL) suspension in the stirred state within 60 minutes. The solution turned brown and the reaction solution was stirred for about 30 min. Then, within 60 minutes, anhydrous DMF (272 mL) dissolved with p-toluenesulfonyl chloride (94.0 g, 492 mmol) was added. After stirring the mixed solution for about 1 h, it was heated to ambient temperature and stirred for about 18 h. Slowly pour the reaction mixture into ice water (6 L) and added 2.5 N NaOH in water (50.0 mL, 125 mmol). Filter the sediment to collect and stirred 3 times with cold water (200 mL). Finally, the collected products were filtered and dried to a constant weight in a vacuum oven at about 55 °C to obtain N-Tosyl-5-bromo-4,7-diazaindole (134.6 g, 97%).
N-Tosyl-5-bromo-4,7-diazaindole

Safety

N-Tosyl-5-bromo-4,7-diazaindole can cause skin irritation, severe eye irritation, and possibly respiratory irritation.

References

[1] Yael Ross, Marina Magrey, Use of upadacitinib in the treatment of psoriatic arthritis, Immunotherapy, 2021, 13.
[2] Lina Serhal, Christopher J Edwards, Upadacitinib for the treatment of rheumatoid arthritis, Expert Review of Clinical Immunology, 2018, 15,13-25.
[3] Eleni Kotsiliti, Upadacitinib therapy for Crohn’s disease, Nature Reviews Gastroenterology & Hepatology, 2023, 20, 483.

N-Tosyl-5-bromo-4,7-diazaindole Preparation Products And Raw materials

Raw materials

5-Bromo-4,7-diazaindole 5-[(4-methylphenyl)sulfonyl]-5H-Pyrrolo[2,3-b]pyrazin-2-amine 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine Tosyl chloride

Preparation Products

tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate

N-Tosyl-5-bromo-4,7-diazaindole Suppliers

Global( 168)Suppliers
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Stereokem Pvt Ltd +91-4029706929 +91-9394224843 Telangana, India 350 58 Inquiry
VGS SYNTHESIS PRIVATE LIMITED +91-9866975588 +91-9866975588 Hyderabad, India 1818 58 Inquiry
Stereokem, Inc. 500039 New Delhi, India 293 58 Inquiry
CLEARSYNTH LABS LTD. +91-22-45045900 Hyderabad, India 6351 58 Inquiry
A.J Chemicals 91-9810153283 New Delhi, India 6124 58 Inquiry
SynZeal Research Pvt Ltd +1 226-802-2078 Gujarat, India 6522 58 Inquiry
Golden Pharma Co., Limited +undefined18958062155 China 5905 58 Inquiry
Hangzhou ICH Biofarm Co., Ltd +86-0571-28186870; +undefined8613073685410 China 985 58 Inquiry
Henan Fengda Chemical Co., Ltd +86-371-86557731 +86-13613820652 China 20296 58 Inquiry
ATK CHEMICAL COMPANY LIMITED +undefined-21-51877795 China 32760 60 Inquiry
Supplier Advantage
Stereokem Pvt Ltd 58
VGS SYNTHESIS PRIVATE LIMITED 58
Stereokem, Inc. 58
CLEARSYNTH LABS LTD. 58
A.J Chemicals 58
SynZeal Research Pvt Ltd 58
Golden Pharma Co., Limited 58
Hangzhou ICH Biofarm Co., Ltd 58
Henan Fengda Chemical Co., Ltd 58
ATK CHEMICAL COMPANY LIMITED 60

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1201186-54-0(N-Tosyl-5-bromo-4,7-diazaindole)Related Search:

1-Pyrrolidinecarboxylic acid, 3-(2-bromoacetyl)-4-ethyl-, phenylmethyl ester, (3S,4S)- 1-Pyrrolidinecarboxylic acid, 3-[2-[(ethoxycarbonyl)[5-[(4-methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]amino]acetyl]-4-ethyl-, phenylmethyl ester, (3S,4S)- 1-Pyrrolidinecarboxylic acid, 3-(2-chloroacetyl)-4-ethyl-, phenylmethyl ester, (3R,4S)- INDEX NAME NOT YET ASSIGNED 5-Bromo-4,7-diazaindole
N-Tosyl-5-bromo-4,7-diazaindole 2-Bromo-5-[(4-methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazine 2-BROMO-5-(P-TOLYLSULFONYL)-5H-PYRROLO[2,3-B]PYRAZINE 2-bromo-5-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyrazine 2-bromo-5-(4-methylbenzenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine Upadacitinib Impurity 2 2-BroMo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine 5H-Pyrrolo[2,3-b]pyrazine, 2-bromo-5-[(4-methylphenyl)sulfonyl]- Glycerol(Glycerophosphoric acid) 3-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine Upadacitinib Impurity 45 Upatinib Impurity 2 Upatinib Impurity 45 2-BroMo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine,N-Tosyl-5-bromo-4,7-diazaindole 1201186-54-0 Azaindoles