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

Base Information

• Chemical Name: 3-(4-(2-(piperidin-1-yl)propan-2-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]dipyridine-6-carbonitrile
• CAS No.: 1200126-74-4
• Molecular Formula: C₂₅H₂₅N₅
• Molecular Weight: 395.507
• Mol file: 1200126-74-4.mol

Synonyms:

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

There total 12 articles about 3-(4-(2-(piperidin-1-yl)propan-2-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:

1.4-dibromobenzene (106-37-6) → 3-(4-(2-(piperidin-1-yl)propan-2-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]dipyridine-6-carbonitrile (1200126-74-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: magnesium; iodine / diethyl ether / 0.08 h / Inert atmosphere; Reflux

1.2: 1.5 h / Reflux

2.1: bis-triphenylphosphine-palladium(II) chloride; caesium carbonate / water; 1,2-dimethoxyethane / 0.5 h / 140 °C / Microwave irradiation

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 55 °C

With bis-triphenylphosphine-palladium(II) chloride; tetrabutyl ammonium fluoride; iodine; caesium carbonate; magnesium; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; water; 2.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.jmedchem.5b00464

Reference yield:

2-methyl-2-(1-piperidinyl)propanenitrile (2273-41-8) → 3-(4-(2-(piperidin-1-yl)propan-2-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]dipyridine-6-carbonitrile (1200126-74-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: magnesium; iodine / diethyl ether / 0.08 h / Inert atmosphere; Reflux

1.2: 1.5 h / Reflux

2.1: bis-triphenylphosphine-palladium(II) chloride; caesium carbonate / water; 1,2-dimethoxyethane / 0.5 h / 140 °C / Microwave irradiation

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 55 °C

With bis-triphenylphosphine-palladium(II) chloride; tetrabutyl ammonium fluoride; iodine; caesium carbonate; magnesium; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; water; 2.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.jmedchem.5b00464

Reference yield:

methyl 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate bis hydrochloride salt → 3-(4-(2-(piperidin-1-yl)propan-2-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]dipyridine-6-carbonitrile (1200126-74-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: pyridine / 1 h / 100 °C

2.1: pyridine; selenium(IV) oxide / 1,4-dioxane / 100 °C

3.1: acetic acid; sodium acetate; bromine / 1.5 h / 100 °C

4.1: ammonia / methanol / 140 °C / Autoclave

5.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 4 h / 20 °C

6.1: sodium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

6.2: 0 - 20 °C

7.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; dimethyl sulfoxide / 18 h / 120 °C / Sealed tube; Inert atmosphere

8.1: bis-triphenylphosphine-palladium(II) chloride; caesium carbonate / water; 1,2-dimethoxyethane / 0.5 h / 140 °C / Microwave irradiation

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 55 °C

With pyridine; selenium(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutyl ammonium fluoride; ammonia; bromine; potassium acetate; sodium acetate; caesium carbonate; acetic acid; triethylamine; trifluoroacetic anhydride; sodium iodide; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 8.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.jmedchem.5b00464

upstream raw materials:

1.4-dibromobenzene

2-methyl-2-(1-piperidinyl)propanenitrile

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

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

Refernces

• 1、 -. "DIAZACARBAZOLES AND METHODS OF USE". Page/Page column 182, 185. . Retrieved 2010/01/07.