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HomeProduct name listN-Tosyl-5-bromo-4,7-diazaindole

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

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

What is N-Tosyl-5-bromo-4,7-diazaindole?

The Uses of N-Tosyl-5-bromo-4,7-diazaindole

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.

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

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

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for N-Tosyl-5-bromo-4,7-diazaindole

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