1H-Pyrazolo[3,4-b]pyridine-5-carbonitrile

Base Information

• Chemical Name: 1H-Pyrazolo[3,4-b]pyridine-5-carbonitrile
• CAS No.: 1234616-67-1
• Molecular Formula: C7H4N4
• Molecular Weight: 144.133
• Hs Code.: 2933990090
• Mol file: 1234616-67-1.mol

Synonyms:1H-Pyrazolo[3,4-b]pyridine-5-carbonitrile;(E)-tert-Butyl 5-(3-methoxy-3-oxoprop-1-en-1-yl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Chemical Property of 1H-Pyrazolo[3,4-b]pyridine-5-carbonitrile

Chemical Property:

• Boiling Point: 397.1±22.0 °C(Predicted)
• PKA: 8.11±0.40(Predicted)
• PSA: 83.31000
• Density: 1.44±0.1 g/cm3(Predicted)
• LogP: 2.40070
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98% ^*data from raw suppliers

(E)-tert-Butyl5-(3-methoxy-3-oxoprop-1-en-1-yl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (E)-tert-Butyl 5-(3-methoxy-3-oxoprop-1-en-1-yl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate is used in preparation of novel bifunctional compounds as IRAK degraders.

Technology Process of 1H-Pyrazolo[3,4-b]pyridine-5-carbonitrile

There total 3 articles about 1H-Pyrazolo[3,4-b]pyridine-5-carbonitrile 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: 90.0%

zinc(II) cyanide (557-21-1) + 5-bromo-7-azaindazole (875781-17-2,916257-29-9) → 1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (1234616-67-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1-methyl-pyrrolidin-2-one; at 92 ℃; for 5h; Temperature;

Reference yield:

5-bromo-2-fluoropyridine (766-11-0) → 1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (1234616-67-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 3 h / -65 - -30 °C / Inert atmosphere

1.2: 0.08 h

2.1: hydrazine hydrate / tetrahydrofuran; ethanol; water / 1 h / 45 - 80 °C / Large scale

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 10 h / 85 °C / Inert atmosphere; Large scale

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; hydrazine hydrate; diisopropylamine; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

Reference yield:

5-bromo-2-fluoro-3-pyridinecarboxaldehyde (875781-15-0) → 1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (1234616-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrazine hydrate / water / 15 h / 65 °C / Inert atmosphere

2: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / water; N,N-dimethyl acetamide / 6 h / 80 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; hydrazine hydrate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl acetamide; water;

DOI:10.1021/acs.joc.7b01101

upstream raw materials:

zinc(II) cyanide

5-bromo-7-azaindazole

5-bromo-2-fluoropyridine

5-bromo-2-fluoro-3-pyridinecarboxaldehyde

Downstream raw materials:

1H-pyrazolo[3,4-b] pyridine-5-carboxylic acid

1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid methyl ester

4-chloro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile