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

Base Information

• Chemical Name: N-Tosyl-5-bromo-4,7-diazaindole
• CAS No.: 1201186-54-0
• Molecular Formula: C13H10BrN3O2S
• Molecular Weight: 352.211
• Hs Code.: 2933990090
• Mol file: 1201186-54-0.mol

Synonyms:2-Bromo-5-[(4-methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazine; 2-Bromo-5-(4-methylphenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine

Chemical Property of N-Tosyl-5-bromo-4,7-diazaindole

Chemical Property:

• Boiling Point: 499.6±55.0 °C(Predicted)
• PKA: -2.22±0.30(Predicted)
• PSA: 73.23000
• Density: 1.68±0.1 g/cm3(Predicted)
• LogP: 3.82000
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-Tosyl-5-bromo-4,7-diazaindole

There total 6 articles about N-Tosyl-5-bromo-4,7-diazaindole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

2-bromo-5H-pyrrolo[2,3-b]pyrazine (875781-43-4) + p-toluenesulfonyl chloride (98-59-9) → 2-bromo-5-(p-toluenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine (1201186-54-0)

Guidance literature:

2-bromo-5H-pyrrolo[2,3-b]pyrazine; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 5 ℃; for 0.5h;

p-toluenesulfonyl chloride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield: 86.9%

5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine (875781-41-2) + p-toluenesulfonyl chloride (98-59-9) → 2-bromo-5-(p-toluenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine (1201186-54-0)

Guidance literature:

2-bromo-5-p-toluenesulfonyl-5H-pyrrolo[2,3-b]pyrazine; With sodium t-butanolate; In N,N-dimethyl acetamide; at 50 - 60 ℃; for 1h;

p-toluenesulfonyl chloride; In N,N-dimethyl acetamide; at 20 ℃; for 1h; Temperature;

Reference yield:

C13H11N3O3S → 2-bromo-5-(p-toluenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine (1201186-54-0)

Guidance literature:

With hydrogen bromide;

upstream raw materials:

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

p-toluenesulfonyl chloride

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

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

Downstream raw materials:

(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

(3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate

Refernces

• 1、 Bhagavatula, Lakshmi,Christesen, Alan,Dunn, Travis B.,Ickes, Andrew,Kotecki, Brian J.,Marek, James C.,Morrill, Westin H.,Moschetta, Eric,Mulhern, Mathew,Rasmussen, Michael,Reynolds, Troy,Rozema, Michael J.,Yu, Su. "Development of a Scalable Enantioselective Synthesis of JAK Inhibitor Upadacitinib". . . Retrieved 2021/10/21.
• 2、 -. "Influenza virus replication inhibitors and uses thereof (by machine translation)". Paragraph 0415; 0421-0422. . Retrieved 2019/10/01.