Category: 149108-61-2

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

Kudo, Noriaki published the artcileA versatile method for Suzuki cross-coupling reactions of nitrogen heterocycles, COA of Formula: C15H14BNO4S, the publication is Angewandte Chemie, International Edition (2006), 45(8), 1282-1284, database is CAplus and MEDLINE.

A wide-ranging study of Suzuki reactions which use nitrogen-containing heterocycles was described. This method was highly versatile (a single procedure was used for all substrates, including boronate esters and trifluoroborates), compatible with a variety of unprotected functionalities (e.g., NH₂– and OH-substituted substrates), and efficient even with inactivated aryl chlorides.

Angewandte Chemie, International Edition 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, COA of 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

Kudo, Noriaki published the artcileA versatile method for Suzuki cross-coupling reactions of nitrogen heterocycles, COA of Formula: C15H14BNO4S, the publication is Angewandte Chemie, International Edition (2006), 45(8), 1282-1284, database is CAplus and MEDLINE.

A wide-ranging study of Suzuki reactions which use nitrogen-containing heterocycles was described. This method was highly versatile (a single procedure was used for all substrates, including boronate esters and trifluoroborates), compatible with a variety of unprotected functionalities (e.g., NH₂– and OH-substituted substrates), and efficient even with inactivated aryl chlorides.

Angewandte Chemie, International Edition 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, COA of 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

Yang, Cai-Guang published the artcilePreparing Functional Bis(indole) Pyrazine by Stepwise Cross-coupling Reactions: An Efficient Method to Construct the Skeleton of Dragmacidin D, Formula: C15H14BNO4S, the publication is Journal of Organic Chemistry (2002), 67(26), 9392-9396, database is CAplus and MEDLINE.

A direct approach for selective construction of properly substituted bis(indole) pyrazine I, the skeleton of a marine alkaloid dragmacidin D, has been developed. The key steps involved the regioselective introduction of two indole units, using the palladium(0)-catalyzed Suzuki and the Stille cross-coupling reactions sequentially.

Journal of Organic 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 C40H35N7O8, 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

Wang, Ke published the artcileSynthesis and antitumor activity of bisindolylmaleimide and amino acid ester conjugates, Computed Properties of 149108-61-2, the publication is Journal of Asian Natural Products Research (2010), 12(1), 36-42, database is CAplus and MEDLINE.

A series of novel bisindolylmaleimide and natural amino acid ester conjugates were synthesized and evaluated for their inhibitory activity against six tumor cell lines. Some compounds displayed interesting cytotoxic profiles. The most active compound 8e showed inhibitory activity against several human cancer cell lines.

Journal of Asian Natural Products Research 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 C21H24O8, Computed Properties of 149108-61-2.

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

Lukashev, Nikolay V. published the artcile6-Chloro- and 6-bromo-substituted steroids in the Suzuki-Miyaura cross-coupling reaction. A convenient route to potential aromatase inhibitors, SDS of cas: 149108-61-2, the publication is Synthesis (2006), 533-539, database is CAplus.

Chlorine at an sp²-carbon in steroids was shown to be reactive in Suzuki-Miyaura cross-coupling reactions with either Ni or Pd catalysts. The coupling of analogous 6-bromo derivatives was also demonstrated to be applicable to a wider scope of substrates. The Suzuki-Miyaura arylation of 6-bromo-螖^3,5-steroid enol ethers with subsequent hydrolysis is a useful route to 6-arylated steroids bearing aryl at a saturated carbon.

Synthesis 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, SDS of cas: 149108-61-2.

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

Krishnamoorthy, Ravi published the artcilePalladium-Catalyzed Preparation of Weinreb Amides from Boronic Acids and N-Methyl-N-methoxycarbamoyl Chloride, Product Details of C15H14BNO4S, the publication is Journal of Organic Chemistry (2010), 75(4), 1251-1258, database is CAplus and MEDLINE.

A simple protocol for the synthesis of Weinreb benzamides and 伪,尾-unsaturated Weinreb amides through a palladium-catalyzed cross-coupling reaction between organoboronic acids and N-methoxy-N-methylcarbamoyl chloride has been developed. The method is also applicable to the use of potassium organotrifluoroborates.

Journal of Organic 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 C15H14BNO4S, Product Details of 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

Tobrman, Tomas published the artcileAluminum chloride promoted cross-coupling of trisubstituted enol phosphates with organozinc reagents en route to stereoselective synthesis of tamoxifen and its analogues, Product Details of C15H14BNO4S, the publication is European Journal of Organic Chemistry (2016), 2016(29), 5037-5044, database is CAplus.

In the presence of Pd(S-Phos)₂Cl₂ [S-Phos = (2′,6′-dimethoxy-1,1-biphenyl-2-yl)dicyclohexylphosphine], aluminum chloride acts as a promoter for the diastereoselective Negishi coupling reactions of arylzinc chlorides or tribenzylaluminum (generated in situ) with enol phosphates to yield aryl alkenes with high stereoselectivities; using dibromoalkenyl phosphates, tri- and tetraaryl alkenes were prepared stereoselectively. Using this method, tamoxifen and two analogs were prepared stereoselectively in >98:2 diastereoselectivities.

European Journal of Organic 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 C10H15NO, Product Details of 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