Tag: M.W=300-350

Gong, Liang published the artcileNi-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers, Safety of 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, the publication is Journal of the American Chemical Society (2019), 141(19), 7680-7686, database is CAplus and MEDLINE.

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Journal of the American Chemical Society published new progress about 1206163-56-5. 1206163-56-5 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, and the molecular formula is C21H24BNO2, Safety of 1-Benzyl-5-(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

Gong, Liang published the artcileNi-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers, Safety of 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, the publication is Journal of the American Chemical Society (2019), 141(19), 7680-7686, database is CAplus and MEDLINE.

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Journal of the American Chemical Society published new progress about 1206163-56-5. 1206163-56-5 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, and the molecular formula is C21H24BNO2, Safety of 1-Benzyl-5-(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

Lim, Yee Hwee published the artcileDirect Conversion of Indoles to 3,3-Difluoro-2-oxindoles via Electrophilic Fluorination, Name: 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, the publication is Organic Letters (2012), 14(22), 5676-5679, database is CAplus and MEDLINE.

3,3-Difluoro-2-oxindoles can be obtained directly from indoles in moderate yields via electrophilic fluorination using N-fluorobenzenesulfonimide as a mild fluorinating reagent. The presence of tert-Bu hydroperoxide during the reaction, together with addnl. heating after quenching the reaction with triethylamine, is beneficial to the formation of the desired product.

Organic Letters published new progress about 1206163-56-5. 1206163-56-5 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, and the molecular formula is C21H24BNO2, Name: 1-Benzyl-5-(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

Chowdhury, Rajdip published the artcileN-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C-H alkylation of indoles, Safety of 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, the publication is Chemical Communications (Cambridge, United Kingdom) (2021), 57(37), 4532-4535, database is CAplus and MEDLINE.

Despite the extensive studies on the reactions between conventional diazocompounds and indoles, these are still limited by the independent synthesis of the carbene precursors, the specific catalysts, and the required multi-step manipulation of the products. In this work, use of redox-active carbenes in the expedited and divergent synthesis of functionalized indoles is reported. NHPI-DA displays unusual efficiency and selectivity to yield insertion products that can be swiftly elaborated into boron and carbon substituents that are particularly problematic in carbene-mediated reactions.

Chemical Communications (Cambridge, United Kingdom) published new progress about 1206163-56-5. 1206163-56-5 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, and the molecular formula is C21H24BNO2, Safety of 1-Benzyl-5-(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

Axten, Jeffrey M. published the artcileDiscovery of 7-methyl-5-(1-{[3-(trifluoromethyl)phenyl]acetyl}-2,3-dihydro-1H-indol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (GSK2606414), a potent and selective first-in-class inhibitor of protein kinase R (PKR)-like endoplasmic reticulum kinase (PERK), HPLC of Formula: 837392-67-3, the publication is Journal of Medicinal Chemistry (2012), 55(16), 7193-7207, database is CAplus and MEDLINE.

Protein kinase R (PKR)-like endoplasmic reticulum kinase (PERK) is activated in response to a variety of endoplasmic reticulum stresses implicated in numerous disease states. Evidence that PERK is implicated in tumorigenesis and cancer cell survival stimulated our search for small mol. inhibitors. Through screening and lead optimization using the human PERK crystal structure, we discovered compound I (GSK2606414), an orally available, potent, and selective PERK inhibitor. Compound I inhibits PERK activation in cells and inhibits the growth of a human tumor xenograft in mice.

Journal of Medicinal Chemistry published new progress about 837392-67-3. 837392-67-3 belongs to indole-building-block, auxiliary class Indoline,Boronic acid and ester,Amide,Boronate Esters,Aliphatic Heterocyclic, name is tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-1-carboxylate, and the molecular formula is C19H28BNO4, HPLC of Formula: 837392-67-3.

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

Wang, Ke published the artcileSynthesis of Arcyriarubin A and Arcyriaflavin A via Cross-Coupling of Indolylboronic Acid with Dibromomaleimides, Recommanded Product: (1-tosyl-1H-Indol-3-yl)boronic acid, the publication is Synthetic Communications (2010), 40(1), 144-150, database is CAplus.

Arcyriarubin A (I) was first isolated by Steglich in 1980 and is also a key intermediate in the synthesis of indolocarbazole alkaloids. A new synthetic approach to the natural products arcyriaflavin A (II) and arcyriarubin A was described. The key step was a Suzuki cross-coupling reaction which was achieved by refluxing 1-tosyl-3-indolylboronic acid, 1-methyl-3,4-dibromomaleimide, Pd(PPh₃)₄ and Na₂CO₃ in dioxane/MeOH. The preparation of arcyriaflavin A was accomplished in eight steps from indole with an overall yield of 21%.

Synthetic Communications published new progress about 149108-61-2. 149108-61-2 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Sulfamide,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (1-tosyl-1H-Indol-3-yl)boronic acid, and the molecular formula is C15H21BO2, Recommanded Product: (1-tosyl-1H-Indol-3-yl)boronic acid.

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

Zou, Ning published the artcileSolution-Phase Synthesis of a Thiazoyl-Substituted Indolyl Library via Suzuki Cross-Coupling, Name: (1-tosyl-1H-Indol-3-yl)boronic acid, the publication is Journal of Combinatorial Chemistry (2003), 5(6), 754-755, database is CAplus and MEDLINE.

The solution phase synthesis of a thiazolyl substituted indolyl library using a Suzuki cross-coupling of 2-chlorothiazole and N-tosyl-3-indolylboronic acids is presented. This library is being evaluated for biol. activity and is a part of a further study for pharmaceutical drug discovery.

Journal of Combinatorial Chemistry published new progress about 149108-61-2. 149108-61-2 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Sulfamide,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (1-tosyl-1H-Indol-3-yl)boronic acid, and the molecular formula is C34H40F2S4, Name: (1-tosyl-1H-Indol-3-yl)boronic acid.

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

Wright, Jay S. published the artcileSequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes, HPLC of Formula: 2304635-05-8, the publication is Journal of the American Chemical Society (2021), 143(18), 6915-6921, database is CAplus and MEDLINE.

This article describes a sequential Ir/Cu-mediated process for the meta-selective C-H radiofluorination of (hetero)arene substrates. In the first step, Ir-catalyzed C(sp²)-H borylation affords (hetero)aryl pinacolboronate (BPin) esters. The intermediate organoboronates are then directly subjected to copper-mediated radiofluorination with [¹⁸F]tetrabutylammonium fluoride to afford fluorine-18 labeled (hetero)arenes in high radiochem. yield and radiochem. purity. This entire process is performed on a bench top without Schlenk or glove box techniques and circumvents the need to isolate (hetero)aryl boronate esters. The reaction was automated on a TracerLab FX_FN module with 1,3-dimethoxybenzene and a meta-tyrosine derivative The products, [¹⁸F]1-fluoro-3,5-dimethoxybenzene and an ¹⁸F-labeled meta-tyrosine derivative, were obtained in 37 ± 5% isolated radiochem. yield and >99% radiochem. purity and 25% isolated radiochem. yield and 99% radiochem. purity, and 0.52 Ci/μmol (19.24 GBq/μmol) molar activity (A_m), resp.

Journal of the American Chemical Society published new progress about 2304635-05-8. 2304635-05-8 belongs to indole-building-block, auxiliary class Boronate Esters,Boronic Acids,Boronic acid and ester, name is Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-4-carboxylate, and the molecular formula is C10H23N, HPLC of Formula: 2304635-05-8.

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

Garg, Neil K. published the artcileThe First Total Synthesis of Dragmacidin D, Formula: C15H14BNO4S, the publication is Journal of the American Chemical Society (2002), 124(44), 13179-13184, database is CAplus and MEDLINE.

The first total synthesis of the biol. significant bis-indole alkaloid dragmacidin D has been achieved. Thermal and electronic modulation provides the key for a series of palladium-catalyzed Suzuki cross-coupling reactions that furnished the core structure of the complex guanidine- and aminoimidazole-containing dragmacidins. Thus, 6-bromo-3-iodo-2-methoxypyrazine was coupled with bromoindole I in the presence of Pd(PPh₃)₄/MeOH/C₆H₆/Na₂CO₃/H₂O to give indolopyrazine II. II was then coupled with another indole under similar conditions to give the core silylated bisindole pyrazine III. Following this crucial sequence, a succession of meticulously controlled final events was developed leading to the completion of the natural product.

Journal of the American Chemical Society published new progress about 149108-61-2. 149108-61-2 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Sulfamide,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (1-tosyl-1H-Indol-3-yl)boronic acid, and the molecular formula is C15H14BNO4S, Formula: C15H14BNO4S.

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

Thadani, Avinash N. published the artcileStereospecific Synthesis of Highly Substituted Skipped Dienes through Multifunctional Palladium Catalysis, Name: (1-tosyl-1H-Indol-3-yl)boronic acid, the publication is Organic Letters (2002), 4(24), 4317-4320, database is CAplus and MEDLINE.

Skipped dienes I [R = H, Me, EtCH₂, Bu, MeO₂C; R¹ = H, EtCH₂, Ph, TBSOCH₂, HOCMe₂; R² = H, Me; R³ = Br, 4-MeOC₆H₄, 3-MeCOC₆H₄, 3-O₂NC₆H₄, Ph, 1-tosyl-3-indolyl, (E)-PhCH:CH, (E)-BuCH:CH; TBS = Me₃CSi(Me)₂] were prepared stereoselectively in one-pot processes from allyl chloride or bromide, alkynes, and boronic acids. Alkenyl bromides I (R = H, EtCH₂, Bu, Ph; R¹ = H, EtCH₂, MeO₂C; R² = Br; R³ = H) were prepared in 82-87% yields by addition of alkynes RCCR¹ dropwise to solutions of the palladium catalyst PdBr₂(PhCN)₂ with allyl bromide in DME. Under these conditions, the palladium catalyst did not decompose to palladium black, suggesting that further palladium-catalyzed processes might proceed in the same pot. Skipped alkenes I [R = H, Me, EtCH₂, Bu, MeO₂C; R¹ = H, EtCH₂, Ph, TBSOCH₂, HOCMe₂; R² = H, Me; R³ = 4-MeOC₆H₄, 3-MeCOC₆H₄, 3-O₂NC₆H₄, Ph, 1-tosyl-3-indolyl, (E)-PhCH:CH, (E)-BuCH:CH; TBS = Me₃CSi(Me)₂] were prepared in 79-86% yields by addition of alkynes RCCR¹ in THF dropwise to solutions of the palladium catalyst PdBr₂(PhCN)₂ with either allyl bromide or methallyl bromide in THF at 0° and warming to ambient temperature over 6 h followed by addition of boronic acids R²B(OH)₂, tri(tert-butyl)phosphine, and cesium carbonate to the solution and stirring for 16 h at ambient temperature Tri(tert-butyl)phosphine was the best ligand for the Suzuki coupling; 1,3-bis(2,4,6-trimethylphenyl)dihydroimidazolium chloride was also an effective ligand. Bases other than cesium carbonate were not as effective in the Suzuki coupling reaction. Dropwise addition of alkyne allowed the reactions to be conducted in the presence of. Skipped alkenes I [R = H, Me, EtCH₂, Bu, MeO₂C; R¹ = H, EtCH₂, Ph, TBSOCH₂, HOCMe₂; R² = H; R³ = 4-MeOC₆H₄, 3-MeCOC₆H₄, 3-O₂NC₆H₄, Ph; TBS = Me₃CSi(Me)₂] were also prepared in 64-73% yields using allyl chloride instead of allyl bromide; the Suzuki coupling reaction required heating at 45° to achieve good yields of product.

Organic Letters published new progress about 149108-61-2. 149108-61-2 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Sulfamide,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (1-tosyl-1H-Indol-3-yl)boronic acid, and the molecular formula is C9H8O4, Name: (1-tosyl-1H-Indol-3-yl)boronic acid.

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