57786-47-7

Upstream product

• 3731-51-9 2-(Aminomethyl)pyridine 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100-09-4 4-methoxybenzoic acid 
• 696-63-9 4-Methoxybenzenethiol 
• 201230-82-2 carbon monoxide 

Downstream Products

• 610276-99-8 3-(4-methoxyphenyl)imidazo[1,5-a]pyridine-1-carbaldehyde 
• 1310584-30-5 3-(E)-1-[3-(4-methoxyphenyl)imidazo[1,5-a]pyridin-1-yl]methylidene-2-indolinone 
• 1310584-31-6 3-(E)-1-[3-(4-methoxyphenyl)imidazo[1,5-a]pyridin-1-yl]methylidene-1-methyl-2-indolinone 
• 1310584-32-7 5-fluoro-3-(E)-1-[3-(4-methoxyphenyl)imidazo[1,5-a]pyridin-1-yl]methylidene-2-indolinone 
• 906668-55-1 1-iodo-3-(4-methoxyphenyl)imidazo[1,5-a]pyridine 

Relevant academic research and scientific papers

Cobalt catalysed aminocarbonylation of thiols in batch and flow for the preparation of amides

The synthesis of amides from thiols through a cobalt-catalyzed aminocarbonylation is shown. After optimizing all the reaction parameters, the methodology makes possible the obtention of amides with variable yields, while competing reactions such as the formation of disulfides and ureas can be limited. The process works well with aromatic thiols with electron donating groups (EDG) whereas other thiols give reaction with lower yields. The previous process has been transferred and optimized into flow equipment, thus allowing using less CO in a safer way, and permitting the scaling up of the synthesis. Two drugs, moclobemide and itopride were prepared with this methodology, albeit only in the second case with good results. A mechanistic pathway is proposed.

Synthesis of 3-aryl-1-phosphinoimidazo[1,5-a]pyridine ligands for use in Suzuki-Miyaura cross-coupling reactions

3-Aryl-1-phosphinoimidazo[1,5-a]pyridine ligands were synthesized from 2-aminomethylpyridine as the initial substrateviatwo complementary routes. The first synthetic pathway underwent the coupling of 2-aminomethylpyridine with substituted benzoyl chlorides, followed by cyclization, iodination and palladium-catalyzed cross-coupling phosphination reactions sequence to give our phosphorus ligands. In the second route, 2-aminomethylpyridine was cyclized with aryl aldehydes, followed by the iodination and palladium-catalyzed cross-coupling phosphination reactions to yield our phosphorus ligands. The 3-aryl-1-phosphinoimidazo[1,5-a]pyridine ligands were evaluated in palladium-catalyzed sterically-hindered biaryl and heterobiaryl Suzuki-Miyaura cross-coupling reactions.

Thionyl chloride-mediated synthesis of 2-azaindolizine sulfur-bridged dimers by C-H bond direct chalcogenation of imidazo[1,5-a]pyridines

Thionyl chloride-mediated chalcogenation of imidazo[1,5-a]pyridine serves as a new protocol for the synthesis of rare bisimidazopyridyl sulfides. This method provides the new route to synthesis of 2-azaindolizine sulfur-bridged dimers called chalcogenide

Synthesis of (Z)-3-(arylamino)-1-(3-phenylimidazo[1,5-a]pyridin-1-yl)prop-2-en-1-ones as potential cytotoxic agents

The new derivatives based on (Z)-3-(arylamino)-1-(3-phenylimidazo[1,5-a]pyridin-1-yl)prop-2-en-1-one scaffold was synthesized and evaluated for their in vitro cytotoxic potential against a panel of cancer cell lines, viz., A549 (human lung cancer), HCT-116 (human colorectal cancer), B16F10 (murine melanoma cancer), BT-474 (human breast cancer), and MDA-MB-231 (human triple-negative breast cancer). Among them, many of the synthesized compounds exhibited promising cytotoxic potential against the panel of tested cancer cell lines with IC50 50 value of 1.21 ± 0.14 μM. Flow cytometric analysis revealed that compound 15i arrested the G0/G1 phase of the cell cycle. Moreover, increased reactive oxygen species (ROS) generation, clonogenic assay, acridine orange staining, DAPI nuclear staining, measurement of mitochondrial membrane potential (ΔΨm), and annexin V-FITC assays revealed that compound 15i promoted cell death through apoptosis.

Cobalt-catalyzed carbonylative synthesis of phthalimides from n-(pyridin-2-ylmethyl)benzamides with tfben as the co source

A cobalt-catalyzed direct carbonylative synthesis of phthalimide motifs from N-(pyridin-2-ylmethyl)benzamides has been developed. Various phthalimide derivatives were obtained in moderate to excellent yields (up to 98percent) by using 2-picolylamine as an efficient directing group and benzene-1,3,5-triyl triformate (TFBen) as a convenient CO surrogate.

Synthesis and biological evaluation of new bisindole-imidazopyridine hybrids as apoptosis inducers

A series of diindolylmethanes (5a-t) were designed, synthesized, and examined for their cytotoxicity against four human cancer cell lines like prostate (DU-145), lung (A549), breast (MCF-7) and cervical cancer (HeLa). These results revealed that among all

Synthesis and biological evaluation of imidazo[1,5-a]pyridine-benzimidazole hybrids as inhibitors of both tubulin polymerization and PI3K/Akt pathway

A series of imidazo[1,5-a]pyridine-benzimidazole hybrids (5a-aa) were prepared and evaluated for their cytotoxic activity against a panel of sixty human tumor cell lines. Among them compounds 5d and 5l showed significant cytotoxic activity with GI50

Synthesis and anticancer activity of oxindole derived imidazo[1,5-a] pyrazines

A series of oxindole derivatives of imidazo[1,5-a]pyrazines were prepared and confirmed by 1H NMR, mass and HRMS data. These compounds were evaluated for their anticancer activity against a panel of 52 human tumor cell lines derived from nine d

Nickel-catalyzed chelation-assisted transformations involving ortho C-H bond activation: Regioselective oxidative cycloaddition of aromatic amides to alkynes

Although the pioneering example of ortho metalation involving cleavage of C-H bonds was achieved using a nickel complex (Kleiman, J. P.; Dubeck, M. J. Am. Chem. Soc. 1963, 85, 1544), no examples of catalysis using nickel complexes have been reported. In this work, the Ni-catalyzed transformation of ortho C-H bonds utilizing chelation assistance, such as oxidative cycloaddition of aromatic amides with alkynes, has been achieved.