344324-85-2

Upstream product

• 626-02-8 3-Iodophenol 
• 100-09-4 4-methoxybenzoic acid 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1321604-75-4 C₁₁H₁₇BN₂O 
• 766-85-8 3-methoxy-1-iodobenzene 

Downstream Products

• 1061317-06-3 2-(2-Iodo-5-methoxyphenylthio)-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-4-amine 
• 1061316-78-6 2-(2-iodo-5-methoxyphenylthio)-1-(pent-4-ynyl)-1H-imidazo[4,5-c]pyridin-4-amine 
• 1430348-02-9 4-methoxy-1,2-bis(phenylethynyl)benzene 

Relevant academic research and scientific papers

Facile, One-Pot, and Gram-Scale Synthesis of 3,4,5-Triiodoanisole through a C-H Iodination/ipso-Iododecarboxylation Strategy: Potential Application towards 3,4,5-Trisubstituted Anisoles

A facile, efficient, and gram-scale method for the conversion of para-anisic acid into 3,4,5-triiodoanisole through a one-pot C-H iodination/ipso-iododecarboxylation reaction was investigated. Commercially available benzoic acid was used, which allowed the reaction to be performed on a multigram scale in good yield. This report discloses a practical method for the one-pot synthesis of hitherto unknown 3,4,5-triiodoanisole that is catalytic, scalable, efficient, and easy to work up and purify. Potential application of the target compound as a precursor for novel site-selective metal-iodine exchange and Suzuki-Miyaura cross-coupling reactions were also explored. 3,4,5-Trisubstituted anisole derivatives were provided in a highly regioselective fashion; these compounds are useful building blocks in synthesis and indeed are hard to prepare by any other means. The facile and efficient synthesis of hitherto unknown 3,4,5-triiodoanisole in a tandem one-pot C-H iodination/ipso-iododecarboxylation reaction that is catalytic, scalable, easy to work up, and easy to purify is disclosed. Potential application of the target compound as a precursor for novel site-selective metal-iodine exchange and Suzuki-Miyaura cross-coupling reactions are demonstrated.

Orbital Crossings Activated through Electron Injection: Opening Communication between Orthogonal Orbitals in Anionic C1-C5 Cyclizations of Enediynes

Generally, the long-range electronic communication between spatially orthogonal orbitals is inefficient and limited to field and inductive effects. In this work, we provide experimental evidence that such communication can be achieved via intramolecular electron transfer between two degenerate and mutually orthogonal frontier molecular orbitals (MOs) at the transition state. Interaction between orthogonal orbitals is amplified when the energy gap between these orbitals approaches zero, or at an “orbital crossing”. The crossing between two empty or two fully occupied MOs, which do not lead to stabilization, can be “activated” when one of the empty MOs is populated (i.e., electron injection) or one of the filled MOs is depopulated (i.e., hole injection). In reductive cycloaromatization reactions, such crossings define transition states with energies defined by both the in-plane and out-of-plane π-systems. Herein, we provide experimental evidence for the utility of this concept using orbital crossings in reductive C1-C5 cycloaromatization reactions of enediynes. Communication with remote substituents via orbital crossings greatly enhances regioselectivity of the ring closure step in comparison to the analogous radical cyclizations. We also present photophysical data pertaining to the efficiency of electron injection into the benzannelated enediynes.

Ortho-magnesiation of boron-substituted benzenes by using (TMP) 2Mg

Magnesiation ortho to boron: Borylbenzenes with an N-methyl-1,3- ethylenediamino group on the boron atom undergo ortho-magnesiation upon exposure to 2,2,6,6-tetramethylpiperidide (TMP)2Mg, and the resulting ortho-magnesiated borylbenzenes can be trapped with electrophiles (see scheme).

FUSED AMINO PYRIDINE AS HSP90 INHIBITORS

The present invention relates to HSP90 inhibitors containing fused amino pyridine core that are useful as inhibitors of HSP90 and their use in the treatment of HSP90 related diseases and disorders such as cancer, an autoimmune disease, or a neurodegenerative disease.