N-Tosyl-5-bromo-4,7-diazaindole
- Product Name
- N-Tosyl-5-bromo-4,7-diazaindole
- 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]-;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;2-bromo-5-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyrazine;2-bromo-5-(4-methylbenzenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine
- CBNumber
- CB62470216
- Molecular Formula
- C13H10BrN3O2S
- Formula Weight
- 352.21
- MOL File
- 1201186-54-0.mol
N-Tosyl-5-bromo-4,7-diazaindole Property
- 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)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- B679303
- Product name
- 2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine
- Packaging
- 1g
- Price
- $270
- Updated
- 2021/12/16
- Product number
- B679303
- Product name
- 2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine
- Packaging
- 2.5g
- Price
- $550
- Updated
- 2021/12/16
- Product number
- CS-W009203
- Product name
- 2-Bromo-5-[(4-methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazine
- Packaging
- 10g
- Price
- $608
- Updated
- 2021/12/16
- Product number
- 073334
- Product name
- N-Tosyl-5-bromo-4,7-diazaindole
- Purity
- 95+%
- Packaging
- 1g
- Price
- $639
- Updated
- 2021/12/16
- Product number
- CS-W009203
- Product name
- 2-Bromo-5-[(4-methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazine
- Packaging
- 1g
- Price
- $120
- Updated
- 2021/12/16
N-Tosyl-5-bromo-4,7-diazaindole Chemical Properties,Usage,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].
Uses
either carboxyl or hydroxyl functional. The carboxyl functional are used for hybrids with epoxy resin for indoor applications and for outdoor applications. They are cured with b-hydroxyalkylamides. Hydroxyfunctional polyesters are cured with internal or external blocked isocyanates. The liquid polyesters are intended for highquality 90 % peroxide at<100 C[
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%).
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
Preparation Products
N-Tosyl-5-bromo-4,7-diazaindole Suppliers
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- Product
- 2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine 1201186-54-0
- Price
- US $300.00-7500.00/KG
- Min. Order
- 0.1KG
- Purity
- 98%
- Supply Ability
- 5MT per month
- Release date
- 2023-11-09
- Product
- N-Tosyl-5-bromo-4,7-diazaindole 1201186-54-0
- Price
- US $5.00-0.10/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2024-04-10
- Product
- Upadacitinib Impurity 45 1201186-54-0
- Price
- US $0.00-0.00/mg
- Min. Order
- 10mg
- Purity
- 0.98
- Supply Ability
- 10g
- Release date
- 2024-04-07