3-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]-dipyridine-6-carbonitrile

Base Information

• Chemical Name: 3-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]-dipyridine-6-carbonitrile
• CAS No.: 1200127-66-7
• Molecular Formula: C₂₂H₂₀N₆
• Molecular Weight: 368.441
• Mol file: 1200127-66-7.mol

Synonyms:3-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]-dipyridine-6-carbonitrile

Chemical Property of 3-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]-dipyridine-6-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]-dipyridine-6-carbonitrile

There total 12 articles about 3-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]-dipyridine-6-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: 95.0%

C22H22N6O (1200129-93-6) → 3-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]-dipyridine-6-carbonitrile (1200127-66-7)

Guidance literature:

With triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; at 35 ℃;

DOI:10.1016/j.bmcl.2014.10.063

Reference yield:

methyl 9H-pyrrolo[2,3-b:5,4-c′]dipyridine-6-carboxylate → 3-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]-dipyridine-6-carbonitrile (1200127-66-7)

Guidance literature:

Multi-step reaction with 4 steps

1: bromine; sodium acetate; acetic acid / 100 °C / Sealed tube

2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; acetonitrile / Microwave irradiation

3: ammonia; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide

4: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 35 °C

With bis-triphenylphosphine-palladium(II) chloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ammonia; bromine; sodium acetate; sodium carbonate; benzotriazol-1-ol; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile; 2: |Suzuki-Miyaura Coupling;

DOI:10.1016/j.bmcl.2014.10.063

Reference yield:

methyl 3-bromo-9H-pyrrolo[2,3-b:5,4-c′]dipyridine-6-carboxylate (1200130-50-2) → 3-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]-dipyridine-6-carbonitrile (1200127-66-7)

Guidance literature:

Multi-step reaction with 3 steps

1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; acetonitrile / Microwave irradiation

2: ammonia; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide

3: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 35 °C

With bis-triphenylphosphine-palladium(II) chloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ammonia; sodium carbonate; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile; 1: |Suzuki-Miyaura Coupling;

DOI:10.1016/j.bmcl.2014.10.063

upstream raw materials:

C₂₂H₂₁N₅O₂

C₂₂H₂₂N₆O

(S)-2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid

methyl 3-bromo-9H-pyrrolo[2,3-b:5,4-c′]dipyridine-6-carboxylate

Refernces

• 1、 Gazzard, Lewis,Appleton, Brent,Chapman, Kerry,Chen, Huifen,Clark, Kevin,Drobnick, Joy,Goodacre, Simon,Halladay, Jason,Lyssikatos, Joseph,Schmidt, Stephen,Sideris, Steve,Wiesmann, Christian,Williams, Karen,Wu, Ping,Yen, Ivana,Malek, Shiva. "Discovery of the 1,7-diazacarbazole class of inhibitors of checkpoint kinase 1". . p. 5704 - 5709. Retrieved 2015/01/08.