ChemicalBook > CAS DataBase List > N-Tosyl-5-bromo-4,7-diazaindole

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]-;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
Formula Weight: 352.21
MOL File: 1201186-54-0.mol

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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)
Appearance: Light brown to brown Solid
InChI: InChI=1S/C13H10BrN3O2S/c1-9-2-4-10(5-3-9)20(18,19)17-7-6-11-13(17)15-8-12(14)16-11/h2-8H,1H3
InChIKey: UMZKBENCNNDLRF-UHFFFAOYSA-N
SMILES: C12N(S(C3=CC=C(C)C=C3)(=O)=O)C=CC1=NC(Br)=CN=2

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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.

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N-Bromosuccinimide Price

TRC

Product number: B679303
Product name: 2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine
Packaging: 1g
Price: $270
Updated: 2021/12/16

TRC

Product number: B679303
Product name: 2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine
Packaging: 2.5g
Price: $550
Updated: 2021/12/16

ChemScene

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

Matrix Scientific

Product number: 073334
Product name: N-Tosyl-5-bromo-4,7-diazaindole
Purity: 95+%
Packaging: 1g
Price: $639
Updated: 2021/12/16

ChemScene

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

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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.

Synthesis

875781-41-2

98-59-9

1201186-54-0

To a solution of 5-bromo-3-[(trimethylsilyl)alkynyl]pyrazin-2-amine (3.00 g, 11.1 mmol) in DMF (60 mL) was added NaH (60% dispersed in mineral oil, 0.577 g, 14.4 mmol) in batches at 0 °C. After 15 min of reaction, p-toluenesulfonyl chloride (2.75 g, 14.4 mmol) was added, followed by slow warming of the reaction system to room temperature. After 16 hours of reaction, the mixture was poured into ice water (120 mL) and the precipitate was collected by vacuum filtration. The crude product was dissolved in DCM (15 mL) and purified by silica gel column chromatography, using DCM as eluent. The fractions containing the target product were combined and concentrated under reduced pressure to afford 2-bromo-5-toluenesulfonyl-5H-pyrrolo[2,3-b]pyrazine (2.16 g, 52% yield).LC/MS analysis (see Table 2 for conditions, method d) showed: retention time Rt = 1.58 min; mass spectrum m/z: 352/354 (M+H)+.

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.

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Preparation Products

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View Lastest Price from N-Tosyl-5-bromo-4,7-diazaindole manufacturers

Henan Aochuang Chemical Co.,Ltd.

Product: N-Tosyl-5-bromo-4,7-diazaindole 1201186-54-0
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-10-08

Anhui Dexinjia Biopharm Co., Ltd

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

ShenZhen H&D Pharmaceutical Technology Co., LTD

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

1201186-54-0, N-Tosyl-5-bromo-4,7-diazaindoleRelated 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-tosyl-5H-pyrrolo[2,3-b]pyrazine

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

5H-Pyrrolo[2,3-b]pyrazine, 2-bromo-5-[(4-methylphenyl)sulfonyl]-

Upadacitinib Impurity 2

Glycerol(Glycerophosphoric acid)

3-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

2-BroMo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine,N-Tosyl-5-bromo-4,7-diazaindole

Upadacitinib Impurity 45

Upatinib Impurity 45

Upatinib Impurity 2

1201186-54-0

Azaindoles