cas 155868-51-2, 6-Chloro-1-methyl-1H-indole

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Rhodium(III)-Catalyzed Regioselective C?H Allylation and Prenylation of Indoles at C4-Position
Herein, Rh(III)-catalyzed C4-selective C?H allylation and prenylation of indoles by using a weak carbonyl coordination directing group have been reported. By employing 5-methylene-1,3-dioxan-2-ones, 4-vinyl-1,3-dioxolan-2-ones and 2-methyl-2,3-butadiene as scalable cross-coupling partners, these divergent synthesis protocols proceed smoothly under redox-neutral reaction conditions, delivering various allylated and prenylated indoles in moderate to satisfied yields. This transformation exhibits high functional-groups compatibility and broad substrate scope. Scale-up experiment and mechanistic studies were also accomplished. (Figure presented.).
Zhang, Shang-Shi,Liu, Yan-Zhi,Zheng, Yi-Chuan,Xie, Hui,Chen, Shao-Yong,Song, Jia-Lin,Shu, Bing
supporting information
p. 64 - 70
(2021/11/03)

Multi-fused ring EGFR inhibitor and preparation method and application thereof
The present invention relates to a multi-fused ring EGFR inhibitor and preparation method and application thereof. In particular, the present invention relates to an EGFR inhibitor having a structure of formula (I) and a method of preparation thereof, a p
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Paragraph 0237-0240

(2022/01/10)

Tandem iridium-catalyzed decarbonylative c-h activation of indole: Sacrificial electron-rich ketone-assisted bis-arylsulfenylation
Described herein is a decarbonylative tandem C-H bis-arylsulfenylation of indole at the C2 and C4 C-H bonds through the use of pentamethylcyclopentadienyl iridium dichloride dimer ([Cp?IrCl2]2) catalyst and disulfides. A new sacrificial electron-rich adamantoyl-directing group facilitates indole C-H bis-functionalization with a traceless in situ removal. Various differently substituted disulfides can be easily accommodated in this reaction by a coordination to Ir(III) through the formation of six- and five-membered iridacycles at the C2 and C4 positions, respectively. Mechanistic studies show that a C-H activation-induced C-C activation is involved in the catalytic cycle.
Kathiravan, Subban,Anaspure, Prasad,Zhang, Tianshu,Nicholls, Ian A.
supporting information
p. 3331 - 3336
(2021/05/29)

Visible-Light-Induced Carbonylation of Indoles with Phenols under Metal-Free Conditions: Synthesis of Indole-3-carboxylates
A visible-light-induced carbonylation of indoles with phenols for the synthesis of indole-3-carboxylates has been developed. The reaction proceeded via a radical carbonylation process in which elementary I2 was used as an effective photosensitive initiator and, thus, avoided the use of transition metal catalysts. A series of different aryl indole-3-carboxylates were prepared in moderate to good yields. The broad applicability of this methodology was further highlighted by the late-stage functionalization of several phenol-containing natural products and pharmaceuticals.
Qi, Zhuang,Li, Lin,Liang, Ying-Kang,Ma, Ai-Jun,Zhang, Xiang-Zhi,Peng, Jin-Bao
supporting information
p. 4769 - 4773
(2021/06/28)

Synthesis of 3-halogenated 2,3′-biindoles by a copper-mediated 2,3-difunctionalization of indoles
A copper-mediated 2,3-difunctionalization of indoles to afford 3-halogenated 2,3′-biindoles is described herein. The protocol uses readily available feedstocks and a naturally abundant copper catalyst system, which allows the regioselective formation of C-C and C-X (X = Cl & Br) bonds in one single operation. Here the copper metal salt serves not only as a catalyst but also as a reactant to provide the source of halogen. This operationally simple procedure avoids the utilization of environmentally unfriendly reagents and displays good functional group compatibility. Noteworthily, the introduction of halogen into molecules would offer great potential for further chemical transformations. This journal is
Gu, Xiaoting,Liang, Taoyuan,Wei, Wanxing,Zhang, Xiaoxiang,Zhang, Yingying,Zhang, Zhuan
supporting information
p. 10403 - 10407
(2021/12/17)

Visible-Light-Induced, Base-Promoted Transition-Metal-Free Dehalogenation of Aryl Fluorides, Chlorides, Bromides, and Iodides
We report a simple and efficient visible-light-induced transition-metal-free hydrogenation of aryl halides. The combined visible light and base system is used to initiate the desired radical-mediated hydrogenation. A variety of aryl fluorides, chlorides, bromides, and iodides could be reduced to the corresponding (hetero)arenes with excellent yields under mild conditions. Various functional groups and other heterocyclic compounds are tolerated.
Ding, Ting-Hui,Qu, Jian-Ping,Kang, Yan-Biao
supporting information
p. 3084 - 3088
(2020/04/10)

N-(PHENYL)-INDOLE-3-SULFONAMIDE DERIVATIVES AND RELATED COMPOUNDS AS GPR17 MODULATORS FOR TREATING CNS DISORDERS SUCH AS MULTIPLE SCLEROSIS
Disclosed are N-(phenyl)-lH-indole-3-sulfonamide and N-(phenyl) -1 H-pyrrolo[2,3-b]pyridine-3-sulfonamide derivatives of formula I substituted at the 1- and 6-positions of the 1H-indole or 1H-pyrrolo[2,3-b]pyridine moiety, as well as structurally related
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(2021/01/22)

Sulfoxide-Promoted Chlorination of Indoles and Electron-Rich Arenes with Chlorine as Nucleophile
An efficient chlorination of indoles and electron-rich arenes with chlorine anion as nucleophile is described. With the use of ethyl phenyl sulfoxide as the promoter, the reaction went smoothly under metal-free and mild conditions. Various indoles and electron-rich arenes are converted into the corresponding chlorinated compounds in moderate to excellent yields. A plausible interrupted Pummerer reaction mechanism was proposed without the oxidation of chloride anion. In addition, the byproduct thioether could be easily converted to the starting material sulfoxide just by a simple oxidation reaction. (Figure presented.).
Ji, Yuan-Zhao,Li, Hui-Jing,Wang, Yi-Ruo,Wu, Yan-Chao,Zhang, Zheng-Yan
supporting information

(2020/02/05)

Isothiourea-Catalyzed Enantioselective Synthesis of Tetrahydro-α-carbolinones
An isothiourea-catalyzed enantioselective annulation protocol using indolin-2-imines with a series of α,β-unsaturated p-nitrophenyl esters for the synthesis of tetrahydro-α-carbolinones was developed. Using 5 mol % of the isothiourea HyperBTM as the Lewis base catalyst, this process allows the enantioselective preparation of a range of C(4)-substituted tetrahydro-α-carbolinones in good to excellent yield and with high enantioselectivity (20 examples, 32-99% yield and up to 99:1 er).
Liu, Honglei,Slawin, Alexandra M. Z.,Smith, Andrew D.
supporting information
p. 1301 - 1305
(2020/02/25)

Cobalt-Catalyzed Cycloamination: Synthesis and Photophysical Properties of Polycyclic N-Heterocycles
The first earth-abundant cobalt-catalyzed cycloamination of indolylquinones and various (hetero)aromatic amine under ligand-free conditions for the synthesis of polycyclic N-heterocycles has been developed. The process allows facile access to polycyclic N-heterocycles with tolerance of chloride, bromide, amino, thio, etc. groups in moderate to high yields (up to 89percent). In addition, The photophysical properties of the synthesized products were evaluated. These products exhibit interesting fluorescence properties, which is promising for fluorescent probes.
Dong, Yu,He, Shuai,Shi, Zhi-Chuan,Wang, Ji-Yu,Yang, Jian,Zhan, Xiao-Yu,Zhang, Hua,Zhang, Xiao-Mei
supporting information

(2020/07/15)

Straightforward access to novel indolo[2,3-: B] indoles via aerobic copper-catalyzed [3+2] annulation of diarylamines and indoles
Herein, we report an unprecedented aerobic copper-catalyzed [3+2] annulation reaction of diarylamines with indoles, which allows direct access to novel 2-diarylaminoindolo[2,3-b]indoles, a class of potential photoelectric device molecules. The developed transformation proceeds with broad substrate scope, good functional group tolerance, high chemo-selectivity, and no need for pre-preparation of specific agents, which offers a practical route for diverse and atom-economic synthesis of the desired products that are difficult to prepare with the conventional approaches.
Gong, Lingzhen,Jiang, Huanfeng,Liang, Taoyuan,Zhang, Min,Zhao, He
supporting information
p. 2807 - 2810
(2020/03/13)

γ-Carboline synthesis enabled by Rh(iii)-catalysed regioselective C-H annulation
A redox-neutral Rh(iii)-catalyzed C-H annulation of indolyl oximes was developed. Relying on the use of various alkynyl silanes as the terminal alkyne surrogates, the reaction exhibited a reverse regioselectivity, thus giving an exclusive and easy way for the synthesis of a wide range of substituent free γ-carbolines at C3 position with high efficiency. Deuterium-labelling experiments and kinetic analysis have preliminarily shed light on the working mode of this catalytic system. This journal is
Jiang, Bo,Jia, Jingwen,Sun, Yufei,Wang, Yichun,Zeng, Jing,Bu, Xiubin,Shi, Liangliang,Sun, Xiaoying,Yang, Xiaobo
supporting information
p. 13389 - 13392
(2020/11/10)

Selective Methylation of Amides, N-Heterocycles, Thiols, and Alcohols with Tetramethylammonium Fluoride
We herein disclose the use of tetramethylammonium fluoride (TMAF) as a direct and selective methylating agent of a variety of amides, indoles, pyrroles, imidazoles, alcohols, and thiols. The method is characterized by operational simplicity, wide scope, and ease of purification. Our computational studies suggest a concerted methylation-deprotonation as the preferred reaction pathway.
Cheng, Hong-Gang,Pu, Maoping,Kundu, Gourab,Schoenebeck, Franziska
supporting information
p. 331 - 334
(2019/12/30)

Isodesmic C-H Borylation: Perspectives and Proof of Concept of Transfer Borylation Catalysis
The potential advantages of using arylboronic esters as boron sources in C-H borylation are discussed. The concept is showcased using commercially available 2-mercaptopyridine as a metal-free catalyst for the transfer borylation of heteroarenes using arylboronates as borylation agents. The catalysis shows a unique functional group tolerance among C-H borylation reactions, tolerating notably terminal alkene and alkyne functional groups. The mechanistic investigation is also described.
Rochette, étienne,Desrosiers, Vincent,Soltani, Yashar,Fontaine, Frédéric-Georges
supporting information
p. 12305 - 12311
(2019/08/20)

Switchable regioselection of C-H thiolation of indoles using different TMS counterions
A switchable regioselectivity in C-H thiolation reaction by simply swapping the counteranions of TMS is reported here for the first time. An exclusive C3-H thiolation of indoles with sodium arylsulfinates was achieved in the presence of TMSCl as a promoter. In contrast, with the use of TMSOTf instead of TMSCl under otherwise identical conditions, a regiospecific C2-H thiolation of indoles was realized with the same set of substrates.
Ji, Yuan-Zhao,Li, Hui-Jing,Zhang, Jin-Yu,Wu, Yan-Chao
supporting information
p. 11864 - 11867
(2019/10/11)

Metal-free synthesis of benzimidazo[1,2-c]quinazolin-6-ones with indole and benzenediamine oxidized by I2/TBHP
A variety of benzimidazo[1,2-c]quinazolin-6-ones derivatives can be accessed in moderate to good yields under simple and metal-free reaction conditions using indoles and o-benzenediamines oxidized by iodine and TBHP. This procedure works in reasonable yields for different indoles as well as o-benzenediamines thus may provide a good synthesis of quinazolinones. A TBHP oxidized ring expansion reaction mechanism that explains the synthesis of benzimidazo[1,2-c]quinazolin-6-ones were reported.
Dai, Zhen,Li, Songhua,Li, Yunyi,Feng, Lei,Ma, Chen
supporting information
p. 2012 - 2017
(2019/02/20)

Tandem Rh(III)-Catalyzed C-H Heteroarylation of Indolyl Ketones and Cu(II)-Promoted Intramolecular Cyclization: One-Pot Access to Blue-Emitting Phenanthrone-Type Polyheterocycles
Disclosed herein is a highly efficient one-pot synthetic strategy to phenanthrone-type polyheterocycles via tandem rhodium(III)-catalyzed ortho-C-H heteroarylation of indolyl ketones and copper(II)-promoted intramolecular cyclization. This protocol enables a library of blue-emitting fluorophores with high quantum yields and narrow full widths at half-maximum to be rapidly built from readily available substrates, among of which 6,6,7,9,12-pentamethyl-6,12-dihydro-5H-benzofuro[2,3-a]carbazol-5-one (4a) exhibits pure blue emission with Commission Internationale de I'Eclairage coordinates of (0.15, 0.09) and a high quantum yield of 85% in CH2Cl2 solution.
Pu, Xingwen,Zhang, Mangang,Lan, Jingbo,Chen, Shuyou,Liu, Zheng,Liang, Wenbo,Yang, Yudong,Zhang, Min,You, Jingsong
supporting information
p. 1139 - 1143
(2019/05/16)

Site-Selective 1,1-Difunctionalization of Unactivated Alkenes Enabled by Cationic Palladium Catalysis
A palladium(II)-catalyzed 1,1-difunctionalization of unactivated terminal and internal alkenes via addition of two nucleophiles was developed using a cationic palladium(II) complex. The palladacycle generated in situ as a result of a regioselective addition of a nucleophile to the alkene can readily undergo regioselective β-hydride elimination and migratory insertion with a cationic palladium catalyst. The resulting η3-π-allyl palladium(II) complex is the key intermediate that reacts with a second nucleophile to furnish the desired 1,1-difunctionalization of the alkene. Under the optimized reaction conditions, a wide range of indoles and anilines add to alkene units of 3-butenoic or 4-pentenoic acid derivatives to afford the synthetically useful γ,γ- or δ,δ-difunctionalized products with excellent regiocontrol. Furthermore, by employing internal hydroxyl or acid groups and external carbon nucleophiles, this transformation enables unsymmetric 1,1-difunctionalization to forge challenging and important oxo quaternary carbon centers. Combining experiments and DFT calculations on the mechanism of the reaction is investigated in detail.
Jeon, Jinwon,Ryu, Ho,Lee, Changseok,Cho, Dasol,Baik, Mu-Hyun,Hong, Sungwoo
supporting information

(2019/07/03)

Site-Selective 1,1-Difunctionalization of Unactivated Alkenes Enabled by Cationic Palladium Catalysis
A palladium(II)-catalyzed 1,1-difunctionalization of unactivated terminal and internal alkenes via addition of two nucleophiles was developed using a cationic palladium(II) complex. The palladacycle generated in situ as a result of a regioselective addition of a nucleophile to the alkene can readily undergo regioselective β-hydride elimination and migratory insertion with a cationic palladium catalyst. The resulting η 3-π-allyl palladium(II) complex is the key intermediate that reacts with a second nucleophile to furnish the desired 1,1-difunctionalization of the alkene. Under the optimized reaction conditions, a wide range of indoles and anilines add to alkene units of 3-butenoic or 4-pentenoic acid derivatives to afford the synthetically useful γ,γ-or ?,?-difunctionalized products with excellent regiocontrol. Furthermore, by employing internal hydroxyl or acid groups and external carbon nucleophiles, this transformation enables unsymmetric 1,1-difunctionalization to forge challenging and important oxo quaternary carbon centers. Combining experiments and DFT calculations on the mechanism of the reaction is investigated in detail.
Jeon, Jinwon,Ryu, Ho,Lee, Changseok,Cho, Dasol,Baik, Mu-Hyun,Hong, Sungwoo
supporting information
p. 10048 - 10059
(2019/07/04)

Practical and Scalable Synthesis of Borylated Heterocycles Using Bench-Stable Precursors of Metal-Free Lewis Pair Catalysts
A practical and scalable metal-free catalytic method for the borylation and borylative dearomatization of heteroarenes has been developed. This synthetic method uses inexpensive and conveniently synthesizable bench-stable precatalysts of the form 1-NHR2-2-BF3-C6H4, commercially and synthetically accessible heteroarenes as substrates, and pinacolborane as the borylation reagent. The preparation of several borylated heterocycles on 2 and 50 g scales was achieved under solvent-free conditions without the use of Schlenk techniques or a glovebox. A kilogram-scale borylation of one of the heteroarene substrates was also achieved using this cost-effective green methodology to exemplify the fact that our methodology can be conveniently implemented in fine chemical industries.
Jayaraman, Arumugam,Misal Castro, Luis C.,Fontaine, Frédéric-Georges
supporting information
p. 1489 - 1499
(2018/10/26)

Thioether-Directed Selective C4 C-H Alkenylation of Indoles under Rhodium Catalysis
A thioether-directed Rh(III)-catalyzed C4 selective C-H alkenylation of indoles via the formation of 5-membered metallacycle intermediates is reported. This protocol allows a wide functional group compatibility and broad substrate scope. The directing group can be readily removed or transformed into other functional groups after the C-H functionalization event. The catalytic method is also applicable to related heterocyclic systems involving benzo[b]thiophene and benzo[b]furan scaffolds.
Kona, Chandrababu Naidu,Nishii, Yuji,Miura, Masahiro
supporting information
p. 4898 - 4901
(2018/08/24)

Directly Bridging Indoles to 3,3′-Bisindolylmethanes by Using Carboxylic Acids and Hydrosilanes under Mild Conditions
A straightforward Lewis acid-promoted protocol for 3,3′-bisindolylmethanes (BIMs) synthesis by reductive alkylation of indoles at the C3 position with carboxylic acids in the presence of hydrosilane was developed for the first time. Instead of aldehydes, more readily available, stable, and easy-to-handle carboxylic acids have been employed as alternative alkylating agents. As an efficient organocatalyst, B(C6F5)3 enables the reductive alkylation of various substituted indole derivatives with carboxylic acids with up to 98 % yield at room temperature and under neat conditions. This metal-free strategy offers an alternative approach for the direct functionalization of indoles to BIMs with carboxylic acids and such protocol allows selective reduction of carboxylic acid to aldehyde in combination with C?C bond formation.
Qiao, Chang,Liu, Xiao-Fang,Fu, Hong-Chen,Yang, Hao-Peng,Zhang, Zhi-Bo,He, Liang-Nian
p. 2664 - 2670
(2018/09/14)

Catalytic Access to Indole-Fused Benzosiloles by 2-Fold Electrophilic C-H Silylation with Dihydrosilanes
A protocol for the catalytic synthesis of indole-fused benzosiloles starting from 2-aryl-substituted indoles and dihydrosilanes is reported. Compared to known procedures, this method does not require prefunctionalized starting materials and, hence, allows for a rapid access to those siloles. The net reaction is a 2-fold electrophilic C-H silylation catalyzed by cationic Ru-S complexes. Both reaction steps were separately investigated, and these results eventually led to the development of a two-step procedure. By preparing new Ru-S complexes with different weakly coordinating anions (WCAs), it is also shown that the latter can have a dramatic influence on the outcome of these reactions. Furthermore, the substrate scope of the new method is discussed.
Omann, Lukas,Oestreich, Martin
supporting information
p. 767 - 776
(2017/04/21)

Electronic Nature of Ketone Directing Group as a Key to Control C-2 vs C-4 Alkenylation of Indoles
A novel mode of achieving site selectivity between C-2 and C-4 positions in the indole framework by altering the property of the ketone directing group is disclosed. Methyl ketone, as directing group, furnishes exclusively C-2 alkenylated product, whereas trifluoromethyl ketone changes the selectivity to C-4, indicating that the electronic nature of the directing group controls the unusual choice between a 5-membered and a 6-membered metallacycle. The screening of other carbonyl-derived directing groups reveals that strong and weak directing groups exhibit opposite selectivity. Experimental controls and deuteration experiments lend support to the proposed mechanism.
Lanke, Veeranjaneyulu,Bettadapur, Kiran R.,Prabhu, Kandikere Ramaiah
supporting information
p. 5496 - 5499
(2016/11/17)

Frustrated Lewis Pair Catalyzed Dehydrogenative Oxidation of Indolines and Other Heterocycles
An acceptorless dehydrogenation of heterocycles catalyzed by frustrated Lewis pairs (FLPs) was developed. Oxidation with concomitant liberation of molecular hydrogen proceeded in high to excellent yields for N-protected indolines as well as four other substrate classes. The mechanism of this unprecedented FLP-catalyzed reaction was investigated by mechanistic studies, characterization of reaction intermediates by NMR spectroscopy and X-ray crystal analysis, and by quantum-mechanical calculations. Hydrogen liberation from the ammonium hydridoborate intermediate is the rate-determining step of the oxidation. The addition of a weaker Lewis acid as a hydride shuttle increased the reaction rate by a factor of 2.28 through a second catalytic cycle.
Maier, Alexander F. G.,Tussing, Sebastian,Schneider, Tobias,Fl?rke, Ulrich,Qu, Zheng -Wang,Grimme, Stefan,Paradies, Jan
supporting information
p. 12219 - 12223
(2016/10/13)

N -aminopyridinium salts as precursors for N-centered radicals - Direct amidation of arenes and heteroarenes
Readily prepared N-aminopyridinium salts are valuable precursors for the generation of N-centered radicals. Reduction of these salts by single electron transfer allows for clean generation of amidyl radicals. It is shown that direct radical C-H amination of heteroarenes and arenes can be achieved with N-aminopyridinium salts under mild conditions by using photoredox catalysis.
Greulich, Tobias W.,Daniliuc, Constantin G.,Studer, Armido
supporting information
p. 254 - 257
(2015/03/05)

Lewis acid-catalyzed electrophilic trifluoromethylthiolation of (Hetero)arenes
(N-Trifluoromethylthio)saccharin has been applied as an electrophilic trifluoromethylthiolating reagent for a broad scope of heteroarenes, electron-donating group (EDG)-activated benzenes, and several electron-rich olefins. Iron(III) and gold(III) catalysts showed complementary activity for different substrates.
Wang, Qiang,Qi, Zisong,Xie, Fang,Li, Xingwei
supporting information
p. 355 - 360
(2015/03/05)

Visible light-mediated C-H difluoromethylation of electron-rich heteroarenes
A novel method for visible-light photoredox-catalyzed difluoromethylation of electron-rich N-, O-, and S-containingheteroarenes under mild reaction conditions is developed. Mechanistic investigation indicates that the net C-H difluoromethylation proceeds through an electrophilic radical-type pathway.
Su, Yi-Ming,Hou, Yu,Yin, Feng,Xu, Yue-Ming,Li, Yan,Zheng, Xiaoqi,Wang, Xi-Sheng
supporting information
p. 2958 - 2961
(2014/06/23)

Acid-catalyzed acylation reaction via C-C bond cleavage: A facile and mechanistically defined approach to synthesize 3-acylindoles
A facile acid-catalyzed acylation of indoles with 1,3-dione as an eco-friendly acylating agent was developed. This protocol combines C-C bond cleavage and heterocyclic C-H bond functionalization to form new C-C bonds. Based on the detailed mechanistic studies, a credible mechanistic pathway was proposed. This journal is
Xing, Qi,Li, Pan,Lv, Hui,Lang, Rui,Xia, Chungu,Li, Fuwei
supporting information
p. 12181 - 12184
(2014/12/11)

A general method for palladium-catalyzed direct carbonylation of indole with alcohol and phenol
A novel strategy involving a first oxidative iodination and subsequent Pd0-catalyzed carbonylation to yield indole-3-carboxylate has been developed. It showed perfect generality to indole, alcohol, and phenol. The current methodology could also be conveniently applied to the synthesis of biologically active tropisetron from simple indole and tropine.
Lang, Rui,Shi, Lijun,Li, Dengfeng,Xia, Chungu,Li, Fuwei
supporting information; experimental part
p. 4130 - 4133
(2012/10/07)

Palladium-catalyzed mono- and double-carbonylation of indoles with amines controllably leading to amides and α-ketoamides
A novel and efficient double-carbonylation of indoles with primary or secondary amines to yield indole-3-α-ketoamides has been developed and bioactive molecules could be one-pot synthesized using the current methodology, which could also be selectively switched to mono-carbonylation to afford indole-3-amides only by a slight modification of reaction conditions.
Xing, Qi,Shi, Lijun,Lang, Rui,Xia, Chungu,Li, Fuwei
supporting information
p. 11023 - 11025
(2013/01/15)

Regioselective Rh-catalyzed direct carbonylation of indoles to synthesize indole-3-carboxylates
Rh-catalyzed C-H carbonylation of indoles under 1 atm of CO has been achieved. Various substituted indoles and indole with free N-H could be carboxylated with linear- and/or cyclic-alcohol to give the desired indole-3-carboxylates with up to 92% yield. A mechanism involving Rh III initiated C-H metallation is proposed.
Lang, Rui,Wu, Junliang,Shi, Lijun,Xia, Chungu,Li, Fuwei
supporting information; experimental part
p. 12553 - 12555
(2012/02/02)

Indazolyl-substituted pyrroline compounds as kinase inhibitors
The present invention is directed to novel indazolyl-substituted pyrroline compounds of Formula (I): useful as kinase or dual-kinase inhibitors, methods for producing such compounds and methods for treating or ameliorating a kinase or dual-kinase mediated disorder.
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(2008/06/13)

A practical method for N-methylation of indoles using dimethyl carbonate
A new method for N-methylation of indoles using environmentally safe and less toxic methylating reagent, dimethyl carbonate (DMC), has been developed. The effect of various functional groups on the indole ring has been investigated. This method provides the desired product in high yields with high purity and is suitable for large-scale production. This process was used successfully in a 300-gal reactor train for N-methylation of 6-nitroindole.
Jiang, Xinglong,Tiwari, Ashish,Thompson, Maethonia,Chen, Zhihong,Cleary, Thomas P.,Lee, Thomas B. K.
p. 604 - 608
(2013/09/07)

Methylation of indole compounds using dimethyl carbonate
A process for manufacturing a methylated indole compounds of the formula: where R1is selected from the group consisting of halogen, C1-C6alkyl, C1-C6alkenyl, —OCH3, —NO2, —CHO, —CO2CH3, and —CN, and R2is selected from the group consisting of C1-C6alkyl, —CO2CH3, —CN, —CHO, —NH2, —N(C1-C6alkyl)2, —(CH2)nCOOH, and —(CH2)nCN, where n is an integer from 1 to 4, inclusive, involves reacting a compound of the formula: with dimethyl carbonate in the presence of a base or a catalyst at ambient pressure.
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(2015/09/24)

Indoles as insecticides and acaricides
There are provided methods for the control of insects and the protection of crops from the damage caused thereby which comprise the use of compositions comprising an indole compound of formula I STR1
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(2008/06/13)

Inhibitors of Protein Kinase C. 1. 2,3-Bisarylmaleimides
The design and synthesis of a series of novel inhibitors of protein kinase C (PKC) is described.These 2,3-bisarylmaleimides were derived from the structural lead provided by the indolocarbazoles, staurosporine and K252a.Optimum activity required the imide NH, both carbonyl groups, and the olefinic bond of the maleimide ring. 2,3-Bisindolylmaleimides were the most active, and the potency of these was improved by a chloro substituent at the 5-position of one indole ring (compound 28, IC50 0.11 μM).In a series of (phenylindolyl)maleimides, nitro compound 74 was most active (IC50 0.67 μM).Naphthalene 19 and benzothiophene 21 showed greater than 100-fold selectivity for inhibition of PKC over the closely related cAMP-dependent protein kinase (PKA).
Davis, Peter D.,Hill, Christopher H.,Lawton, Geoffrey,Nixon, John S.,Wilkinson, Sandra E.,et al.
p. 177 - 184
(2007/10/02)