69808-76-0

Upstream product

• 69808-63-5 1-(indole-2-carbonyl)-1H-imidazole 
• 100-46-9 benzylamine 
• 1477-50-5 Indole-2-carboxylic acid 
• 58881-45-1 Indole-2-carbonyl chloride 
• 586959-21-9 1H-1,2,3-benzotriazol-1-yl(1H-indol-2-yl)methanone 

Downstream Products

• 149685-64-3 N-((1H-indol-2-yl)methyl)-1-phenylmethanamine 
• 1316845-35-8 2-benzyl-3-phenyl-4-iodo-5-(3,4-dimethoxyphenyl)-5,10-dihydroazepino[3,4-b]indol-1(2H)-one 
• 1316845-37-0 2-benzyl-3-(4-methylphenyl)-4-iodo-5-(4-ethoxyphenyl)-5,10-dihydroazepino[3,4-b]indol-1(2H)-one 
• 1316845-41-6 2-benzyl-3-cyclohex-1-enyl-4-iodo-5-(4-ethoxyphenyl)-5,10-dihydroazepino[3,4-b]indol-1(2H)-one 
• 1316845-39-2 2-benzyl-3-(4-methylphenyl)-4-iodo-5-(4-chlorophenyl)-5,10-dihydroazepino[3,4-b]indol-1(2H)-one 

Relevant academic research and scientific papers

Cu(OAc)2-Triggered Cascade Reaction of Malonate-Tethered Acyl Oximes with Indoles, Indole-2-alcohols, and Indole-2-carboxamides

A Cu(OAc)2-promoted cascade reaction of malonate-tetherd acyl oximes with indoles, indole-2-alcohols, or indole-2-carboxmides provides facile access to polysubstituted 3-pyrrolin-2-ones. The reaction features the generation of two adjacent elec

HETEROCYCLIC CARBOXYLIC ACID AMIDE LIGAND AND APPLICATIONS THEREOF IN COPPER CATALYZED COUPLING REACTION OF ARYL HALOGENO SUBSTITUTE

Provided are a heterocyclic carboxylic acid amide ligand and applications thereof in a copper catalyzed coupling reaction. Specifically, provided are uses of a compound represented by formula (I), definitions of radical groups being described in the specifications. The compound represented by formula (I) can be used as the ligand in the copper catalyzed coupling reaction of the aryl halogeno substitute, and is used or catalyzing the coupling reaction for forming the aryl halogeno substitute having C—N, C—O, C—S and other bonds.

AMIDATION METHOD AND ESTERIFICATION METHOD USING SULFONIC ACID HALIDE

PROBLEM TO BE SOLVED: To provide a safe and economical method for rapidly synthesizing amides and esters in high yield. SOLUTION: There is provided a method for amidating an amine or a derivative thereof using a sulfonic acid halide, where a sulfonic acid halide is allowed to act as an activator on a carboxylic acid or a derivative thereof to synthesize an active ester, and the active ester is reacted with an amine or a derivative thereof as a nucleophile to amidate the amine or the derivative thereof to obtain a corresponding amide or a derivative thereof. In a similar manner, a sulfonic acid halide is allowed to act as an activator on a carboxylic acid or a derivative thereof to synthesize an active ester, and the active ester is reacted with an alcohol or a derivative thereof as a nucleophile to esterify the alcohol or the derivative thereof to obtain a corresponding ester or a derivative thereof. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2016,JPO&INPIT

Synthesis of heteroarylogous 1H-indole-3-carboxamidines via a three-component interrupted Ugi reaction

A novel one-pot multicomponent synthesis of heteroarylogous 1H-indole-3-carboxamidines starting from readily available N-alkyl-N-(1H-indol-2-ylmethyl)amines, isocyanides, and carbonyl compounds is reported. The strategy exploits the ability of the indole nucleus to interrupt the classical Ugi reaction, by intercepting the nascent nitrilium ion.

Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D2 Receptor Through Fragmentation of a Bitopic Ligand

Recently, we have demonstrated that N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)-1H-indole-2-carboxamide (SB269652) (1) adopts a bitopic pose at one protomer of a dopamine D2 receptor (D2R) dimer to negatively modulate the binding of dopamine at the other protomer. The 1H-indole-2-carboxamide moiety of 1 extends into a secondary pocket between the extracellular ends of TM2 and TM7 within the D2R protomer. To target this putative allosteric site, we generated and characterized fragments that include and extend from the 1H-indole-2-carboxamide moiety of 1. N-Isopropyl-1H-indole-2-carboxamide (3) displayed allosteric pharmacology and sensitivity to mutations of the same residues at the top of TM2 as was observed for 1. Using 3 as an "allosteric lead", we designed and synthesized an extensive fragment library to generate novel SAR and identify N-butyl-1H-indole-2-carboxamide (11d), which displayed both increased negative cooperativity and affinity for the D2R. These data illustrate that fragmentation of extended compounds can expose fragments with purely allosteric pharmacology.

Facile preparation of amides from carboxylic acids and amines with ion-supported Ph3P

Ion-supported Ph3P, 4-(diphenylphosphino)benzyltrimethylammonium bromide (IS-Ph3P), could be used for the facile amidation of a wide range of carboxylic acids with amines in the presence of bromotrichloromethane to provide the corresponding amides in good yields. In the present reaction, the desired amides were obtained in good yields with high purity by simple extraction of the reaction mixture with diethyl ether or chloroform and subsequent removal of the solvent from the extract. Moreover, ion-supported Ph3PO (IS-Ph3PO), which was a co-product derived from IS-Ph3P in the present reductive condensation, was recovered in high yield and could be reduced to IS-Ph3P for reuse in the same amidation of carboxylic acid.

Synthesis of iodo-indoloazepinones in an iodine-mediated three-component domino reaction via a regioselective 7-endo-dig iodo-cyclization pathway ±

An efficient and rapid synthetic strategy for the naturally occurring indoloazepinone scaffold via a three-component reaction of indole-2- carboxamides, 1,3-disubstituted propargyl alcohols, and I2 is described. The strategy involves a C-H functionalization-alkyne activation-intramolecular hydroamidation-deprotonation domino sequence. The salient feature of this sequence is regioselective electrophilic 7-endo-dig iodo-cyclization during the intramolecular hydroamidation to afford a seven-membered azepinone ring annulated to the indole.

Synthesis, structure-activity relationships and molecular modeling studies of new indole inhibitors of monoamine oxidases A and B

New monoamine oxidase inhibitors were synthesized as indole analogues of a previously reported pyrrole series. Several compounds were potent MAO-A (12, 17, 19-22, 31, 36, and 37) or MAO-B (14, 20, 24, 38, 44, and 46) inhibitors, and had Ki values in the nanomolar concentration range. In particular, 22 (Ki = 0.00092 μM, and SI = 68,478) was exceptionally potent and selective as MAO-A inhibitor. In molecular modeling studies, compounds 22, 24, 44, and 46 positioned the indole ring into an aromatic cavity of MAO-A, and established π-π stacking interactions with Tyr407, Tyr444, and FAD cofactor. However, only compound 22 was able to form hydrogen bonds with FAD, a finding which was in accordance with its potent anti-MAO-A activity. Conversely, 22/MAOB complex was highly unstable during the MD simulation.

Efficient microwave access to polysubstituted amidines from imidoylbenzotriazoles

Microwave reactions of primary and secondary amines with imidoylbenzotriazoles 6a-w gave diversely substituted amidines 7a-Aa in 76-94% yields. Convenient preparations of a variety of amides 5a-Ab (87-96%) and imidoylbenzotriazoles 6a-w (56-95%) have also been developed using microwave irradiation under mild conditions and short reaction times. These results demonstrate further the advantages of microwave synthesis and introduce a new application of imidoylbenzotriazoles in the preparation of polysubstituted amidines.