Tag: M.W=250-300

Wu, Fan published the artcileOxyamination of Unactivated Alkenes with Electron-Rich Amines and Acids via a Catalytic Triiodide Intermediate, Name: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Organic Letters (2020), 22(3), 884-890, database is CAplus and MEDLINE.

An aerobic catalytic oxidation process is described for the olefin oxyamination using acids and primary amines as the sources of O and N. Our mechanistic findings point to the formation of triiodide as a critical catalytic intermediate to account for the tolerance of electron-rich nucleophiles. This dual iodide and copper catalytic system is suitable for a formal [5+1] annulation process to access valuable lactam structures and highlighted by the synthesis of the pharmaceutical Zamifenacin.

Organic Letters published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Name: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Trost, Barry M. published the artcileEnantioselective Divergent Synthesis of C19-Oxo Eburnane Alkaloids via Palladium-Catalyzed Asymmetric Allylic Alkylation of an N-Alkyl-α,β-unsaturated Lactam, Application In Synthesis of 167015-84-1, the publication is Journal of the American Chemical Society (2019), 141(12), 4811-4814, database is CAplus and MEDLINE.

The C19-oxo-functionalized eburnane alkaloids display a unique chem. structure and interesting biol. activity. Herein, we report a divergent enantioselective strategy to access these alkaloids by use of a challenging palladium-catalyzed asym. allylic alkylation of N-alkyl-α,β-unsaturated lactam I. 19-(S)-OH-Δ¹⁴-Vincamone (II, phutdonginin), (-)-19-OH-eburnamine (III), (+)-19-oxoeburnamine (IV), and (+)-19-OH-eburnamonine (V) have been concisely synthesized for the first time in 11 to 13 steps.

Journal of the American Chemical Society published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C22H18O2, Application In Synthesis of 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Uno, Tetsuo published the artcileNew submonomers for poly N-substituted glycines (peptoids), Application of tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Tetrahedron Letters (1999), 40(8), 1475-1478, database is CAplus.

Five protected submonomers for peptoid synthesis were prepared, i.e., Nⁱⁿ-BOC-tryptamine, O-t-butyltyramine, PMC-guanidino-propylamine, 6-amino-6-deoxy-D-galactopyranose diacetonide, and 5-amino-2,2-dimethyl-1,3-dioxane. The first three mimic natural amino acid side chains, i.e., tryptophan, tyrosine, and arginine, while the last two provide hydrophilic side chains. These submonomers were successfully used for preparation of oligo-peptoids by the submonomer synthesis method.

Tetrahedron Letters published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C7H16Cl2Si, Application of tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Newar, Rajashree published the artcileSingle-Site Cobalt-Catalyst Ligated with Pyridylimine-Functionalized Metal-Organic Frameworks for Arene and Benzylic Borylation, Quality Control of 919119-59-8, the publication is Inorganic Chemistry (2020), 59(15), 10473-10481, database is CAplus and MEDLINE.

A highly active single-site heterogeneous cobalt-catalyst is reported based on a porous and robust pyridylimine-functionalized metal-organic frameworks (pyrim-MOF) for chemoselective borylation of arene and benzylic C-H bonds. The pyrim-MOF having UiO-68 topol., constructed from zirconium-cluster secondary building units and pyridylimine-functionalized dicarboxylate bridging linkers, was metalated with CoCl₂ followed by treatment of NaEt₃BH to give the cobalt-functionalized MOF-catalyst (pyrim-MOF-Co). Pyrim-MOF-Co has a broad substrate scope, allowing the C-H borylation of halogen-, alkoxy-, alkyl-substituted arenes as well as heterocyclic ring systems using B₂pin₂ or HBpin (pin = pinacolate) as the borylating agent to afford the corresponding arene- or alkyl-boronate esters in good yields. Pyrim-MOF-Co gave a turnover number (TON) of up to 2500 and could be recycled and reused at least 9 times. Pyrim-MOF-Co was also significantly more robust and active than its homogeneous control, highlighting the beneficial effect of active-site isolation within the MOF framework that prevents intermol. decomposition The exptl. and computational studies suggested (pyrim^â€?)Co^I(THF) as the active catalytic species within the MOF, which undergoes a mechanistic pathway of oxidative addition, turnover limiting σ-bond metathesis, followed by reductive elimination to afford the boronate ester. The pyridylimine-functionalized metal-organic framework (pyrim-MOF)-based single-site cobalt-catalyst is efficient for chemoselective borylation of arene and benzylic C-H bonds. The heterogeneous MOF-catalyst is significantly more robust and active than its homogeneous control, highlighting the beneficial effect of active-site isolation within the MOF framework that prevents intermol. decomposition

Inorganic Chemistry published new progress about 919119-59-8. 919119-59-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C15H20BNO2, Quality Control of 919119-59-8.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Newar, Rajashree published the artcileMono-Phosphine Metal-Organic Framework-Supported Cobalt Catalyst for Efficient Borylation Reactions, Recommanded Product: 2-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is European Journal of Inorganic Chemistry (2022), 2022(10), e202101019, database is CAplus.

The authors report a metal-organic framework (MOF) supported monoligated phosphine-Co complex, which is an active heterogeneous catalyst for aromatic C-H borylation and alkene hydroboration. The mono(phosphine)-Co catalyst (MOF-P-Co) was prepared by metalation of a porous triarylphosphine-functionalized MOF (MOF-P) with CoCl₂ followed by activation with NaEt₃BH. The MOF catalyst has a broad substrate scope with excellent functional group tolerance to afford arene- and alkyl-boronate esters in excellent yields and selectivity. MOF-P-Co gave a turnover number (TON) of 30,000 and could be recycled and reused at least 13 times in arene C-H borylation. Importantly, the attempt to prepare the homogeneous control (Ph₃P-Co) using PPh₃ was unsuccessful due to the facile disproportionation reactions or intermol. ligand exchanges in the solution In contrast, the site isolation of the active mono(phosphine)-Co species within the MOF affords the robust and coordinatively unsaturated metal complexes, allowing to explore their catalytic properties and the reaction mechanism.

European Journal of Inorganic Chemistry published new progress about 919119-59-8. 919119-59-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C15H20BNO2, Recommanded Product: 2-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Jacquemard, Ulrich published the artcileMild and selective deprotection of carbamates with Bu₄NF, Application of tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Tetrahedron (2004), 60(44), 10039-10047, database is CAplus.

A mild method allowing the deprotection of carbamates using TBAF in THF is reported. Reaction was performed on indole, indoline, N-Me aniline, aniline, and tryptamine derivatives The observed selectivity according to the carbamates or the substrates is discussed. A mechanism is also postulated.

Tetrahedron published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Application of tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Wesche, Frank published the artcileCombined approach of backbone amide linking and on-resin N-methylation for the synthesis of bioactive and metabolically stable peptides, Recommanded Product: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Journal of Medicinal Chemistry (2018), 61(9), 3930-3938, database is CAplus and MEDLINE.

Rhabdopeptides are a large class of nonribosomal peptides from the bacteria Xenorhabdus and Photorhabdus with low micromolar activity against different protozoa, which are the causative agents of several tropical diseases. The development of a facile and flexible synthesis combining backbone amide linking with on-resin peralkylation for the synthesis of permethylated rhabdopeptides is described. This strategy allows the fast generation of permethylated naturally occurring and artificial rhabdopeptides for a structure-activity study. Furthermore, in vitro experiments revealed their superior properties regarding their stability and passive membrane diffusion.

Journal of Medicinal Chemistry published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C18H28N2O7, Recommanded Product: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zhang, Dengyou published the artcileDiscovery of novel 2-aminopyridine-3-carboxamides as c-Met kinase inhibitors, Category: indole-building-block, the publication is Bioorganic & Medicinal Chemistry (2012), 20(17), 5169-5180, database is CAplus and MEDLINE.

A series of 2-aminopyridine-3-carboxamide derivatives against c-Met were designed and synthesized by employing bioisosteric replacement of heterocyclic moieties with the amide bond. The structure-activity relationship (SAR) at various positions of the scaffold was explored. In this study, a promising compound (S)-24o (I) with a c-Met IC₅₀ of 0.022 μM was identified. The compound exhibited dose-dependent inhibition of the phosphorylation of c-Met as well as downstream signaling in EBC-1 cells. Furthermore, the interactive binding model of (S)-24o with c-Met was elucidated by virtue of a mol. modeling study.

Bioorganic & Medicinal Chemistry published new progress about 837392-64-0. 837392-64-0 belongs to indole-building-block, auxiliary class Indoline,Boronic acid and ester,Amide,Boronate Esters, name is 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one, and the molecular formula is C12H23N3S, Category: indole-building-block.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles