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1075-35-0, 5-Chloro-2-methylindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 4Synthesis of CBX0024-(2-(5-chloro-2-methyl-lH-indol-l-yl)ethyl)morpholine[0157] To a solution of 2-chloroethylmorpholine HC1 (100 mg, 0.60 mmol) in 0.3 mL DMSO was added pulverized KOH (102 mg, 1.81 mmol), then after 10 min, a solution of 5- chloro-2-methylindole (134 mg, 0.72 mmol) in 0.2 mL DMSO was added and the reaction stirred at room temperature overnight. Additional 2-chloroethylmorpholine (22 mg, 0.12 mmol) and KOH (17 mg, 0.3 mmol) added and stirred overnight. The reaction mixture was partitioned between ?0 and toluene, and the organic extract washed two times with ?0, dried over MgS04, filtered, and concentrated in vacuo. The crude product was purified via silica gel chromatography using a gradient from 0 to 5% MeOH in (?(? to give a final yield of 154 mg (0.55 mmol). XH NMR (500 MHz, CDC13, delta): 2.47 (s, 3H), 2.48-2.57 (m, 4H), 2.63 (t, J = 7.2 Hz, 2H), 3.73 (t, J = 4.4 Hz, 4H), 4.16 (t, J = 7.2 Hz, 2H), 6.20 (s, 1H), 7.1 1 (dd, J = 8.6 Hz, 1.7 Hz, 1H), 7.19 (d, J = 8.6 Hz, 1H), 7.50 (d, J = 1.5 Hz, 1H). 13C NMR (500 MHz, CDC13, delta): 12.88, 41.23, 54.13, 57.86, 66.95, 99.88, 109.78, 1 19.15, 120.64, 124.97, 129.18, 134.99, 138.03. MS m/z 279.3 [M + H]+., 1075-35-0

The synthetic route of 1075-35-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITY OF WASHINGTON THROUGH ITS CENTER FOR COMMERCIALIZATION; STELLA, Nephi; KLINE, Toni; WO2012/24670; (2012); A2;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Copper-catalyzed carbonylative transformations of indoles with hexaketocyclohexane

With hexaketocyclohexane octahydrate as the carbon monoxide source, a novel procedure for copper-catalyzed direct double carbonylation of indoles has been established. Using alcohols as reaction partners, moderate to good yields of the desired double carbonylation products have been obtained. Wide functional group tolerance and substrate scope can be observed.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Organocatalytic asymmetric arylation of indoles enabled by azo groups

Arylation is a fundamental reaction that can be mostly fulfilled by electrophilic aromatic substitution and transition-metal-catalysed aryl functionalization. Although the azo group has been used as a directing group for many transformations via transition-metal-catalysed aryl carbon-hydrogen (C-H) bond activation, there remain significant unmet challenges in organocatalytic arylation. Here, we show that the azo group can effectively act as both a directing and activating group for organocatalytic asymmetric arylation of indoles via formal nucleophilic aromatic substitution of azobenzene derivatives. Thus, a wide range of axially chiral arylindoles have been achieved in good yields with excellent enantioselectivities by utilizing chiral phosphoric acid as catalyst. Furthermore, highly enantioenriched pyrroloindoles bearing two contiguous quaternary chiral centres have also been obtained via a cascade enantioselective formal nucleophilic aromatic substitution-cyclization process. This strategy should be useful in other related research fields and will open new avenues for organocatalytic asymmetric aryl functionalization.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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One-pot synthesis of 7-aryl-octahydroazonino[5,4-b]indoles based on the fragmentation of indolizino[8,7-b]indoles and the insertion of indoles and 3,4,5-trimethoxyphenol

A series of 7-aryl-octahydroazonino[5,4-b]indoles were prepared in one pot via a three component reaction from indolizino[8,7-b]indoles, alpha-chloroethyl chloroformate (ACE-Cl) and activated arenes such as indoles and 3,4,5-trimethoxyphenol. Georg Thieme Verlag Stuttgart.

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. Quality Control of: 5-Chloro-2-methylindole, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 1075-35-0, in my other articles.

Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Palladium-Catalyzed Oxidative Sulfenylation of Indoles and Related Electron-Rich Heteroarenes with Aryl Boronic Acids and Elemental Sulfur

An efficient and convenient palladium-catalyzed C-H bond oxidative sulfenylation of indoles and related electron-rich heteroarenes with aryl boronic acids and elemental sulfur has been described. This procedure provides a useful and direct approach for the assembly of a wide range of structurally diverse 3-sulfenylheteroarenes with moderate to excellent yields from simple and readily available starting materials. Moreover, this synthetic protocol is suitable for N-protected and unprotected indoles. Notably, the construction of two C-S bonds in one step was also achieved in this transformation.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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1075-35-0, 5-Chloro-2-methylindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 4Synthesis of CBX0024-(2-(5-chloro-2-methyl-lH-indol-l-yl)ethyl)morpholine[0157] To a solution of 2-chloroethylmorpholine HC1 (100 mg, 0.60 mmol) in 0.3 mL DMSO was added pulverized KOH (102 mg, 1.81 mmol), then after 10 min, a solution of 5- chloro-2-methylindole (134 mg, 0.72 mmol) in 0.2 mL DMSO was added and the reaction stirred at room temperature overnight. Additional 2-chloroethylmorpholine (22 mg, 0.12 mmol) and KOH (17 mg, 0.3 mmol) added and stirred overnight. The reaction mixture was partitioned between ?0 and toluene, and the organic extract washed two times with ?0, dried over MgS04, filtered, and concentrated in vacuo. The crude product was purified via silica gel chromatography using a gradient from 0 to 5% MeOH in (?(? to give a final yield of 154 mg (0.55 mmol). XH NMR (500 MHz, CDC13, delta): 2.47 (s, 3H), 2.48-2.57 (m, 4H), 2.63 (t, J = 7.2 Hz, 2H), 3.73 (t, J = 4.4 Hz, 4H), 4.16 (t, J = 7.2 Hz, 2H), 6.20 (s, 1H), 7.1 1 (dd, J = 8.6 Hz, 1.7 Hz, 1H), 7.19 (d, J = 8.6 Hz, 1H), 7.50 (d, J = 1.5 Hz, 1H). 13C NMR (500 MHz, CDC13, delta): 12.88, 41.23, 54.13, 57.86, 66.95, 99.88, 109.78, 1 19.15, 120.64, 124.97, 129.18, 134.99, 138.03. MS m/z 279.3 [M + H]+., 1075-35-0

The synthetic route of 1075-35-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITY OF WASHINGTON THROUGH ITS CENTER FOR COMMERCIALIZATION; STELLA, Nephi; KLINE, Toni; WO2012/24670; (2012); A2;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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1075-35-0 5-Chloro-2-methylindole 70636, aindole-building-block compound, is more and more widely used in various fields.

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A mixture of 5-chloro-2-methylindole (30.1 g; 0.18 mole) and 1-acetyl-imidazolidine-2-one (24 g; 0.18 mole) was added to phosphorous oxychloride (178 ml) and heated to 50 C. After 5 hours, phosphorous oxychloride was evaporated. The residue was treated with ethanol (250 ml) cautiously and maintained at reflux for 3.5 hours. The mixture was concentrated under reduced pressure to half of the orignal volume to obtain a precipitate, which was collected on a filter. The crystalline residue was treated with water, washed with ethylacetate, treated with 2N sodium hydroxide to pH 11 and stirred overnight. The precipitate was filtered, washed with water and t-butylmethylether and dried to give product (10.9 g, 26%), m.p. 213 C. [0467] 1H-NMR(DMSO): d 2.5 (s, 3H, CH-31), 3.55 (s, 4H, 2¡ÁCH-2), 6.30 (b, 1H, imidazolin), 7.04 (d, 1H 8.00 (s, 1H, H-4), 11.57 (b, 1H, NH-indol); MS (Ei 70 eV) m/Z 233M+., 1075-35-0

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Reference£º
Patent; Takeuchi, Kumiko; Jirousek, Michael Robert; Paal, Michael; Ruhter, Gerd; Schotten, Theo; US2004/9976; (2004); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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1075-35-0, 5-Chloro-2-methylindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a. A mixture consisting of 100 gm (0.6 mol) of 5-chloro-2-methyl-indole, 100 gm (0.65 mol) of 4-piperidone monohydrate hydrochloride, 900 ml of glacial acetic acid and 450 ml of 4 N phosphoric acid was heated for 2 hours at 80C. Thereafter, the reaction mixture was cooled and then poured into a mixture of ice and ammonia, and the resulting mixture was extracted with ethyl acetate. The organic extract solution was washed with water, dried and evaporated, and the residue was recrystallized from methanol, yielding 108 gm (73% of theory) of 4-(5′-chloro-2′-methyl-3′-indolyl)-1,2,5,6-tetrahydropyridine, m.p. 208-210C., 1075-35-0

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Reference£º
Patent; Boehringer Ingelheim GmbH; US3980658; (1976); A;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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1075-35-0, 5-Chloro-2-methylindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of 2-(3-pyrroline-1-yl) arylaldehydes 1 (0.5mmol, 1.0equiv), indoles 2 (0.55mmol, 1.1equiv) in ethylenechloride (5mL) was added diphenyl phosphite (0.1mmol, 0.1equiv). The mixture was stirred at ambient temperature overnight and the reaction was monitored by TLC. After completed, the reaction was concentrated under reduced pressure and purified by flash chromatography on silica gel (petroleum ether: ethyl acetate=20:1)., 1075-35-0

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Reference£º
Article; Lei, Xiantao; Xie, Hong-Yan; Chen, Si-Yuan; Teng, Kai-Shun; Wen, Xiaoan; Xu, Qing-Long; Sun, Hongbin; Tetrahedron; vol. 71; 24; (2015); p. 4098 – 4101;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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General procedure: Para substituted chalcones (1 equiv.) (9-16) and malononitrile (1equiv.) were stirred in acetonitrile in the presence of L-proline catalyst at room temperature for half an hour. To this reaction mixture different 2-methyl indole (0.8 equiv.) were added and was heated to 90 C on an oil bath. Reaction mixture was stirred till the completion of reaction as monitored by TLC. Afterwards, the reaction mixture was evaporated to dryness under vacumm and was partitioned between ethyl acetate and water. The combined organiclayer was dried and purified by silica gel column chromatographyto get pure products 17-29 [50]., 1075-35-0

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Reference£º
Article; Gupta, Sampa; Maurya, Pooja; Upadhyay, Akanksha; Kushwaha, Pragati; Krishna, Shagun; Siddiqi, Mohammad Imran; Sashidhara, Koneni V.; Banerjee, Dibyendu; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1981 – 1996;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles