Category: 89245-35-2

Saa, Carlos; Crotts, Dallas D.; Hsu, Gishun; Vollhardt, K. Peter C. published an article in Synlett. The title of the article was 《A cobalt-catalyzed entry into the ergot alkaloids: total syntheses of (±)-lysergene and (±)-LSD》.Computed Properties of C10H7BrN2 The author mentioned the following in the article:

Cocyclization of 4-ethynyl-3-indoleacetonitriles with alkynes in the presence of CpCo(CO)2 gives rise to the ergoline derivatives e.g. I (R = CH2OH, CONEt2), which were transformed into racemic lysergene (II) and LSD, resp. The experimental process involved the reaction of 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Computed Properties of C10H7BrN2)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Computed Properties of C10H7BrN2

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Groth, Ulrich; Huhn, Thomas; Kesenheimer, Christian; Kalogerakis, Aris published an article in Synlett. The title of the article was 《Cobalt-mediated regioselective synthesis of substituted tetrahydroquinolines》.Application In Synthesis of 2-(4-Bromo-3-indolyl)acetonitrile The author mentioned the following in the article:

A regioselective synthesis of polycyclic substituted pyridines, e.g., I, is reported. Key step was the cobalt-catalyzed intramol. cyclization of diynenitriles, tethered by a silicon oxygen bond. Subsequent opening of the Si-O ring led then to the related tetrahydroquinolines. The results came from multiple reactions, including the reaction of 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Application In Synthesis of 2-(4-Bromo-3-indolyl)acetonitrile)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Application In Synthesis of 2-(4-Bromo-3-indolyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Egami, Hiromichi; Hotta, Ryo; Otsubo, Minami; Rouno, Taiki; Niwa, Tomoki; Yamashita, Kenji; Hamashima, Yoshitaka published an article in Organic Letters. The title of the article was 《Asymmetric Dearomatizing Fluoroamidation of Indole Derivatives with Dianionic Phase-Transfer Catalyst》.COA of Formula: C10H7BrN2 The author mentioned the following in the article:

Asym. dearomatizing fluorocyclization of indole derivatives was investigated using a dicarboxylate phase-transfer catalyst. This reaction proceeded under mild reaction conditions to provide fluoropyrroloindoline derivatives I [R1 = H, 4-Me, 5-Cl, etc.; R2 = H, Me, Bn, etc.; R3 = SO2Me, 4-MeC6H4SO2, C6H5SO2] in a highly enantioselective manner. Various substitution patterns on the indole ring were well tolerated. To facilitate the reaction and ensure reproducibility, the addition of water was essential and its possible role was discussed. In the part of experimental materials, we found many familiar compounds, such as 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2COA of Formula: C10H7BrN2)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.COA of Formula: C10H7BrN2

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Iwao, Masatomo; Motoi, Osamu published their research in Tetrahedron Letters on August 14 ,1995. The article was titled 《Methodology for the efficient synthesis of 3,4-differentially substituted indoles. Fluoride ion-induced elimination-addition reaction of 1-triisipropylsilylgramine methiodides》.Recommanded Product: 89245-35-2 The article contains the following contents:

1-Triisopropylsilylgramine methiodide reacted smoothly with a variety of nucleophiles in the presence of tetrabutylammonium fluoride to give 3-substituted indoles. The 3,4-disubstituted indoles were efficiently synthesized by sequential use of 4-selective lithiation of 1-triisopropylsilylgramine and this new substitution reaction. The experimental process involved the reaction of 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Recommanded Product: 89245-35-2)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Recommanded Product: 89245-35-2

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Nitrile – Wikipedia,
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Computed Properties of C10H7BrN2On September 18, 2003 ,《Seco-C/D Ring Analogues of Ergot Alkaloids. Synthesis via Intramolecular Heck and Ring-Closing Metathesis Reactions》 was published in Organic Letters. The article was written by Kalinin, Alexey V.; Chauder, Brian A.; Rakhit, Suman; Snieckus, Victor. The article contains the following contents:

Intramol. Heck and ring-closing metathesis reactions on key intermediates I and II, resp., provide efficient entries into seco-C/D ring analogs of Ergot alkaloids III and IV, compounds of potential synthetic and biol. interest. In the experiment, the researchers used many compounds, for example, 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Computed Properties of C10H7BrN2)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Computed Properties of C10H7BrN2

Referemce:
Nitrile – Wikipedia,
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Formula: C10H7BrN2On November 5, 2014 ,《Influences of halogen atoms on indole-3-acetonitrile (IAN): Crystal structure and Hirshfeld surfaces analysis》 appeared in Journal of Molecular Structure. The author of the article were Luo, Yang-Hui; Yang, Li-Jing; Han, Guangjun; Liu, Qing-Ling; Wang, Wei; Ling, Yang; Sun, Bai-Wang. The article conveys some information:

Crystal structural investigations and Hirshfeld surface anal. of three halogen atoms (4-Cl, 6-Cl and 4-Br) substituted indole-3-acetonitrile (IAN) were reported in this work. The structures of the present three compounds were characterized by IR spectra, Elemental analyses, NMR spectra, differential scanning calorimetry (DSC), thermogravimetric analyses (TGA) and hot stage microscopy (HSM). The Hirshfeld surfaces anal. in terms of crystal structure, intermol. interactions and π···π stacking motifs were performed. The authors found that the different kinds of halogen atoms and the different substituted positions have a significant effect on the crystal structures, mol. π···π stacking motifs, m.ps., and the nature of intermol. interactions for IANs.2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Formula: C10H7BrN2) was used in this study.

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Formula: C10H7BrN2

Referemce:
Nitrile – Wikipedia,
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《Enantioselective Total Synthesis of (+)-Lysergic Acid, (+)-Lysergol, and (+)-Isolysergol by Palladium-Catalyzed Domino Cyclization of Allenes Bearing Amino and Bromoindolyl Groups》 was written by Inuki, Shinsuke; Iwata, Akira; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki. Quality Control of 2-(4-Bromo-3-indolyl)acetonitrile And the article was included in Journal of Organic Chemistry on April 1 ,2011. The article conveys some information:

Enantioselective total synthesis of the biol. important indole alkaloids (+)-lysergol (I), (+)-isolyzergol (II), and (+)-lysergic acid (III) is described. Key features of these total synthesis include (1) a facile synthesis of a chiral 1,3-amino alc. via the Pd(0)- and In(I)-mediated reductive coupling reaction between L-serine-derived 2-ethynylaziridine and formaldehyde; (2) the Cr(II)/Ni(0)-mediated Nozaki-Hiyama-Kishi (NHK) reaction of an indole-3-acetaldehyde with iodoalkyne; and (3) Pd(0)-catalyzed domino cyclization of an allene bearing amino and bromoindolyl groups. This domino cyclization enabled direct construction of the C/D ring system of the ergot alkaloids skeleton, as well as the creation of the C5 stereogenic center with transfer of the allenic axial chirality to the central chirality.2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Quality Control of 2-(4-Bromo-3-indolyl)acetonitrile) was used in this study.

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Quality Control of 2-(4-Bromo-3-indolyl)acetonitrile

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Computed Properties of C10H7BrN2On September 25, 1985 ,《The chemistry of indoles. XXIV. Syntheses of 3-indoleacetic acid and 3-indoleacetonitrile having a halo group and a carbon functional group at the 4-position》 was published in Chemical & Pharmaceutical Bulletin. The article was written by Somei, Masanori; Kizu, Kiyomi; Kunimoto, Masako; Yamada, Fumio. The article contains the following contents:

Various 4-halo-3-indoleacetic acids and -3-indoleacetonitriles were synthesized for the first time by means of the Sandmeyer or Schiemann reaction, demonstrating the versatility of 4-indolediazonium salts in 4-substituted indole chem. A practical synthetic method for 4-haloindoles consists of regioselective thallation-halogenation, and the products were also converted to 4-halo-3-indoleacetic acids. The first synthesis of 4-formyl-3-indoleacetonitrile is also reported. The results came from multiple reactions, including the reaction of 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Computed Properties of C10H7BrN2)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Computed Properties of C10H7BrN2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liras, Spiros; Lynch, Christopher L.; Fryer, Andrew M.; Vu, Binh T.; Martin, Stephen F. published an article in Journal of the American Chemical Society. The title of the article was 《Applications of Vinylogous Mannich Reactions. Total Syntheses of the Ergot Alkaloids Rugulovasines A and B and Setoclavine》.Application of 89245-35-2 The author mentioned the following in the article:

Concise syntheses of the Ergot alkaloids rugulovasine A [I; R1 = H, R2 = β-H, R3 = Me, (II)], rugulovasine B I [R1 = H, R2 = α-H, R3 = Me (III)], and setoclavine (IV) have been completed by strategies that feature inter- and intramol. vinylogous Mannich reactions as the key steps. Thus, the first synthesis of II,III commenced with the conversion of the known 4-bromoindole-3-acetonitrile into V via the addition of the 2-(tert-butyldimethylsilyloxy)-3-methylfuran to the iminium ion [VI; CH=N+(Me)Bn], which was generated in situ from the aldehyde VI (R = CHO). Cyclization of V by a novel SRN1 reaction followed by removal of the N-benzyl group furnished a mixture (1:2) of II and III. In an alternative approach to these alkaloids, the biaryl [VII; R = Boc] was reduced with DIBAL-H to give an intermediate imine that underwent spontaneous cyclization via an intramol. vinylogous Mannich addition to provide I [R1 = Boc, R2 = R3 = H]. N-Methylation of the derived benzyl carbamates I [R1 = Boc, R2 = H, R3 = Cbz] followed by global deprotection gave a mixture (2:1) of II and III. IV was then prepared from the biaryl VII (R = Ts) using a closely related intramol. vinylogous Mannich reaction to furnish the spirocyclic lactones I [R1 = Ts, R2 = R3 = H (VIII)]. VIII were subsequently transformed by hydride reduction and reductive methylation into the ergoline derivatives [IX; R = α-OH, β-OH] which were in turn converted into IV by deprotection and solvolytic 1,3-rearrangement of the allylic hydroxyl group. In the experimental materials used by the author, we found 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Application of 89245-35-2)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Application of 89245-35-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liras, Spiros; Lynch, Christopher L.; Fryer, Andrew M.; Vu, Binh T.; Martin, Stephen F. published an article in Journal of the American Chemical Society. The title of the article was 《Applications of Vinylogous Mannich Reactions. Total Syntheses of the Ergot Alkaloids Rugulovasines A and B and Setoclavine》.Application of 89245-35-2 The author mentioned the following in the article:

Concise syntheses of the Ergot alkaloids rugulovasine A [I; R1 = H, R2 = β-H, R3 = Me, (II)], rugulovasine B I [R1 = H, R2 = α-H, R3 = Me (III)], and setoclavine (IV) have been completed by strategies that feature inter- and intramol. vinylogous Mannich reactions as the key steps. Thus, the first synthesis of II,III commenced with the conversion of the known 4-bromoindole-3-acetonitrile into V via the addition of the 2-(tert-butyldimethylsilyloxy)-3-methylfuran to the iminium ion [VI; CH=N+(Me)Bn], which was generated in situ from the aldehyde VI (R = CHO). Cyclization of V by a novel SRN1 reaction followed by removal of the N-benzyl group furnished a mixture (1:2) of II and III. In an alternative approach to these alkaloids, the biaryl [VII; R = Boc] was reduced with DIBAL-H to give an intermediate imine that underwent spontaneous cyclization via an intramol. vinylogous Mannich addition to provide I [R1 = Boc, R2 = R3 = H]. N-Methylation of the derived benzyl carbamates I [R1 = Boc, R2 = H, R3 = Cbz] followed by global deprotection gave a mixture (2:1) of II and III. IV was then prepared from the biaryl VII (R = Ts) using a closely related intramol. vinylogous Mannich reaction to furnish the spirocyclic lactones I [R1 = Ts, R2 = R3 = H (VIII)]. VIII were subsequently transformed by hydride reduction and reductive methylation into the ergoline derivatives [IX; R = α-OH, β-OH] which were in turn converted into IV by deprotection and solvolytic 1,3-rearrangement of the allylic hydroxyl group. In the experimental materials used by the author, we found 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Application of 89245-35-2)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Application of 89245-35-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts