239137-42-9

Upstream product

• 13534-98-0 3-bromopyridin-4-amine 
• 591-50-4 iodobenzene 
• 13534-90-2 dibromo-3,4 pyridine 
• 62-53-3 aniline 
• 13534-99-1 2-Amino-3-bromopyridine 
• 239137-59-8 3-Bromo-4-(2,2-dimethylpropanoylamino)pyridine 
• 70298-89-4 4-N-pivaloylaminopyridine 

Downstream Products

• 1303503-69-6 5-phenyl-5H-pyrido[4,3-b]indole 

Relevant academic research and scientific papers

TRICYCLIC CRBN LIGANDS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of CRBN, and the treatment of CRBN-mediated disorders.

Ultrasound assisted one-pot synthesis of 1,2-diaryl azaindoles via Pd/C-Cu catalysis: Identification of potential cytotoxic agents

Ultrasound assisted one-pot and direct access to 1,2-diaryl substituted azaindole derivatives has been achieved via the sequential N-arylation followed by coupling-cyclization under Pd/C-Cu catalysis. The methodology involved initial C[sbnd]N bond forming

Efficient access to β- and γ-carbolines from a common starting material by sequential site-selective Pd-catalyzed C–C, C–N coupling reactions

Two efficient and practical approaches are reported for the synthesis of β- and γ-carboline derivatives from 3,4-dibromopyridine as a common starting material. The β-carbolines were prepared by site-selective Pd-catalyzed C–C coupling with o-bromophenylboronic acid and subsequent cyclization by double C–N coupling with amines. γ-Carbolines were prepared from the same starting material by C–N coupling with anilines and subsequent annulation by domino C–C/C–N coupling with o-bromophenylboronic acid.

One-pot synthesis of 1, 2-disubstituted 4-, 5-, 6-, and 7-azaindoles from amino-o-halopyridines via n-arylation/sonogashira/cyclization reaction

A direct synthesis of several 1, 2-disubstituted 4-, 5-, 6-, and 7-azaindoles from available amino-o-halopyridines is described. This procedure involves a palladium-catalyzed N-arylation followed by a Sonogashira reaction and subsequent cyclization in a one-pot manner, exhibiting a wide scope and compatibility with electron-withdrawing and electron-donating groups. The strategy represents an advancement in azaindole chemistry with a straightforward approach toward 1, 2-disubstituted azaindoles, while avoiding complex N-arylations of hindered 2-substituted azaindoles and difficult purification steps of intermediates.

Synthesis of Substituted 4-, 5-, 6-, and 7-Azaindoles from Aminopyridines via a Cascade C-N Cross-Coupling/Heck Reaction

A practical palladium-catalyzed cascade C-N cross-coupling/Heck reaction of alkenyl bromides with amino-o-bromopyridines is described for a straightforward synthesis of substituted 4-, 5-, 6-, and 7-azaindoles using a Pd2(dba)3/XPhos/t-BuONa system. This procedure consists of the first cascade C-N cross-coupling/Heck approach toward all four azaindole isomers from available aminopyridines. The scope of the reaction was investigated and several alkenyl bromides were used, allowing access to different substituted azaindoles. This protocol was further explored for N-substituted amino-o-bromopyridines.

Novel synthetic strategy of carbolines via palladium-catalyzed amination and arylation reaction

Four parent carbolines and the corresponding 5- or 9-methylsulfonyl derivatives were synthesized by the palladium-catalyzed intramolecular arylation reaction of ortho-bromo-substituted anilinopyridines which were prepared by the palladium-catalyzed amination reaction of iodobenzenes with aminopyridines. Carbazole and its 9-methylsulfonyl derivative were also synthesized by the same method.