Month: October 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22246-66-8,5-Methoxyisoindolin-1-one,as a common compound, the synthetic route is as follows.

Under an atmosphere of nitrogen, an ice-cooled solution of 6-methoxyisoindolin-1-one (commercially available from for example Astatech) (105 mg, 0.64 mmol) in DMF (2.5 mL) was treated with sodium hydride (60% w/w in mineral oil) (31 mg, 0.77 mmol) and the mixture was allowed to warm to ambient temperature. The mixture was then treated with ethyl 2-bromo-3-methylbutanoate (commercially available from for example Alfa Aesar) (135 mg, 0.64 mmol) and the mixture was stirred for 18 hours then cautiously treated with saturated aqueous ammonium chloride (20 mL). The product was extracted with ethyl acetate (2*25 mL) and the combined organic phase was washed with water (20 mL), brine (20 mL), filtered through a hydrophobic fit and evaporated to dryness. the product was purified by flash chromatography (20 g silica cartridge) using a gradient elution from 0 to 50% ethyl acetate in cyclohexane to afford the title compound (40 mg, 21% yield). LCMS RT=1.03 min, ES+ve m/z 292 [M+H]+

22246-66-8, 22246-66-8 5-Methoxyisoindolin-1-one 22064719, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Crews, Craig M.; Buckley, Dennis; Ciulli, Alessio; Jorgensen, William; Gareiss, Peter C.; Van Molle, Inge; Gustafson, Jeffrey; Tae, Hyun-Seop; Michel, Julien; Hoyer, Dentin Wade; Roth, Anke G.; Harling, John David; Smith, Ian Edward David; Miah, Afjal Hussain; Campos, Sebastien Andre; Le, Joelle; US2014/356322; (2014); 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

16502-01-5, 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(B) will be 516 mg intermediate A dissolved in CH2Cl2In, adding 443 mg of benzoyl chloride (BzCl), under the condition in the ice bath, slowly dropping 455 mg triethylamine (Et3N), stirring at room temperature the reaction 2 h, monitoring after the reaction is complete, the reaction system for CH2Cl2(20 ml) dilution, then adding pure water extraction three times, and finally a saturated salt water, extracted into the organic phase collected drying, turns on lathe does, over silica gel column chromatography separation to obtain 671 mg of intermediate B2, column chromatography in eluting agent is PE/EtOAc=2:1, the reaction yield is 81%; product is a white solid at room temperature.

16502-01-5, 16502-01-5 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole 107838, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Fuzhou University; Chen Haijun; Ye Jinxiang; Wu Jianlei; Lv Tingting; Li Cailong; Gao Yu; (13 pag.)CN106883230; (2017); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.125872-95-9,6-Bromo-1-methyl-1H-indole,as a common compound, the synthetic route is as follows.

Preparation of 2-(6-bromo-1-methyl-1H-indol-3-yl)ethanol To a solution of 6-bromo-1-methyl-1/1-indole (18.0 g, 85.6 mmol) in diethyl ether (180 mL) at 0 C., was added oxalyl chloride (13.1 g, 103 mmol) dropwise under a nitrogen atmosphere. The resulting mixture was allowed to warn to room temperature and stirred for 1 h. After this time, methanol (15 mL) was added and the reaction stirred at room temperature further for 24 h. After this time, the reaction was filtered and the filter cake washed with water (20 mL), then cold diethyl ether (20 mL). The filter cake was dissolved in methylene chloride (100 mL) and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate concentrated under reduced pressure to afford methyl 2-(6-bromo-1-methyl-1H-indol-3-yl)-2-oxoacetate which was used in the next step without purification. A suspension of methyl 2-(6-bromo-1-methyl-1H-indol-3-yl)-2-oxoacetate (18.0 g, 60.8 mmol) in tetrahydrofuran (200 mL) was treated with 2 M borane dimethylsulfide complex in tetrahydrofuran (121 mL) and stirred at reflux for 5 h. After this time, the reaction was cooled to room temperature, diluted with water (50 mL) and saturated aqueous sodium bicarbonate (100 mL) and extracted with diethyl ether (3*250 mL). The combined organic layers were washed sequentially with water and brine, dried over sodium sulfate, filtered and the filtrate concentrated under reduced pressure to afford 2-(6-bromo-1-methyl-1H-indol-3-yl)ethanol as a white solid: 1H NMR (400 MHz, CDCl3) d 7.46 (d, J=8.4 Hz, 1H), 7.46 (d, J=1.6 Hz, 2H), 7.22 (dd, J=8.4, 1.6 Hz, 1H), 6.92 (s, 1H), 3.88 (t, J=6.4 Hz, 2H), 3.73 (s, 3H), 2.99 (t, J=6.4 Hz, 3H).

125872-95-9, 125872-95-9 6-Bromo-1-methyl-1H-indole 15546854, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Gilead Connecticut, Inc.; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Mitchell, Scott A.; Schmitt, Aaron C.; Xu, Jianjun; Zhao, Zhongdong; US2014/148430; (2014); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1477-50-5,1H-Indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Under N2, to a solution of indole-2-formic acid (1.93g, 12mmol) in 120mL of dry Et2O was added19mL of MeLi solution dropwise (1.3M in Et2O, 24mmol) at 0C. The mixture was heated to reflux andkept for 2h and then cooled to room temperature. The saturated NH4Cl solution was added carefully to quench the reaction. The aqueous phase was extracted with Et2O and the combined organic phase waswashed with brine, dried with anhydrous MgSO4 and evaporated in vacuo. The crude product was purified by flash chromatography (PE : EA = 7 : 1) to give a white solid in 53% yield.

1477-50-5, The synthetic route of 1477-50-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wu, Zhijie; Li, Ying; Cai, Yu; Yuan, Junying; Yuan, Chengye; Bioorganic and Medicinal Chemistry Letters; vol. 23; 17; (2013); p. 4903 – 4906;,
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

318-54-7, 2,2,2-Trifluoro-1-(1-methyl-1H-indol-3-yl)ethanol is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a chilled (-780C) solution of 5-bromo-l-(4-fluorophenyl)-3-methyl-l,3-dihydro- benzimidazol-2-one (80 mg, 0.25 mmol) in anhydrous THF (3 mL) was added tert-butyllithium (0.2 mL of 1.7 M solution in heptane, 0.34 mmol). After 1 minute, a chilled (-780C) solution of 2,2,2-trifluoro-l-(l-methyl-lH-indol-3-yl)ethanone (57 mg, 0.25 mmol) in anhydrous TetaF (1 mL) was added. After 10 minutes, the mixture was quenched with ammonium chloride solution and extracted with three 15 mL portions of methylene chloride. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a brownish oil. The residue was purified by column chromatography over silica gel eluting with 0-10% ethyl acetate in methylene chloride to afford 15 mg of the title compound as a white powder. MS m/z 470 (MH+).

318-54-7, 318-54-7 2,2,2-Trifluoro-1-(1-methyl-1H-indol-3-yl)ethanol 3524388, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/70507; (2008); 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

271-34-1, 5-Azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of triethylamine (0.65 ml, 4.66 mmol) and 5-azaindole (1.00 g, 8.46 mmol) in MeCN (20 ml) stirring at 0 00 was added di-teit-butyl dicarbonate (0.97 ml,4.23 mmol) dropwise under nitrogen with stirring. The reaction was allowed to warm to room temperature and left to stir over the weekend. Further di-teit-butyl dicarbonate (0.97 ml, 4.23 mmol) was added and stirring continued for 6 hours. The reaction mixture was concentrated under reduced pressure and the oil obtained taken up in DCM and washed with water. The mixture was passed through a hydrophobic frit and solvent removed under reduced pressure to afford teit-butyl pyrrolo[3,2-c]pyridine-1-carboxylate (P62) (1.76 g), LCMS ES 219 [M+H], Rt = 1.19 mins (Generic Basic Method)., 271-34-1

The synthetic route of 271-34-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; PUGLIESE, Angelo; FRANCIS, Stuart; MCARTHUR, Duncan; SIME, Mairi; BOWER, Justin; BELSHAW, Simone; (315 pag.)WO2019/34890; (2019); 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

93957-49-4, 3-(4-Fluorophenyl)-1-isopropyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

93957-49-4, EXAMPLE 1 3-(4-Fluorophenyl)-1-isopropyl-1H-indole-2-carbaldehyde 5.77 g (78.96 mmol) of DMF are weighed into a 100 ml three-necked round-bottomed flask, equipped with a magnetic stirrer, thermometer, dropping funnel, reflux condenser and nitrogen delivery line, and cooled, with stirring, to 3 C. 12.11 g (78.96 mmol) of phosphorus oxychloride are then slowly added dropwise so that the internal temperature does not exceed 10 C. The reaction mixture is then heated to 80 C. and 10 g (39.48 mmol) of 3-(4-fluorophenyl)-1-isopropyl-1H-indole, dissolved in 10 ml of DMF, are added dropwise in the course of 30 min. Stirring is subsequently carried out for 1.5 hours at that temperature. Cooling and dilution with 10 ml of DMF are then carried out. The reaction mixture is transferred into a dropping funnel and, with stirring, slowly added dropwise at 40 C. to 10 g (0.25 mol) of sodium hydroxide in 200 ml of water. The aqueous phase is extracted four times with 50 ml of toluene and the combined organic phases are washed six times with 100 ml of water. Subsequently, 10 g of silica gel are added, the mixture is stirred for 1 hour and filtration is carried out, followed by washing three times with 50 ml of toluene and concentration by evaporation. 10.17 g of a brown oil are obtained, which is dissolved in 100 ml of hexane under reflux. 10 g of silica gel are added, and filtration is carried out while hot, followed by washing three times with 50 ml of hot hexane. The filtrate is concentrated by evaporation and the residue is recrystallized from 94% ethanol. Slightly beige crystals having a melting point of from 89.5 to 91 C. are obtained.

The synthetic route of 93957-49-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Wolleb, Annemarie; Wolleb, Heinz; US2003/166946; (2003); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.40913-43-7,1-Ethyl-1H-indole-2-carbaldehyde,as a common compound, the synthetic route is as follows.

Intermediate 2 l-Ethyl-3-fluoro-l//-indole-2-carbaldehydeA 50 mL round bottom flask was charged with 1 -ethyl- 1 H- indole-2-carbaldehyde (Intermediate 1, 524 mg, 3.03 mmol) and Selectfluor (1.29 g, 3.64 mmol). MeCN (6.0 mL) was added, and the mixture was allowed to stir at room temperature. After 90 min, the solvent was removed in vacuo, and the residue was partitioned between EtOAc and H2O, and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated. The crude material was purified by silica gel chromatography (gradient elution; Rf in 95:5 hexanes:EtOAc = 0.42) to give a colorless solid (191 mg, 33%) of 90% purity (remainder is unreacted starting material). 1H NMR (400 MHz, CDCl3) delta 1.31 – 1.39 (m, 3 H) 4.52 (q, J=7.07 Hz, 2 H) 7.16 (m, 1 H) 7.34 (m, 1 H) 7.38 – 7.45 (m, 1 H) 7.70 (m, 1 H) 10.08 (s, 1 H). M/Z 191.

40913-43-7, As the paragraph descriping shows that 40913-43-7 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/59238; (2008); 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

348640-06-2, 4-Bromo-7-azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

As shown in Scheme 6,4-bromo-1H-pyrrolo[2,3-b]pyridine (1.01 g), 2-acetamidophenylboronic acid (1.63 g), Pd(PPh3)4 (0.345 mg), and 1M Na2CO3 (8 mL) were mixed in DME (20 mL) and heated at 95 C. overnight. The reaction was cooled and water (60 mL) added. Extraction with dichloromethane (3¡Á) and concentration of the combined organic extracts gave N-(2-(1H-pyrrolo[2,3-b]pyridin-4-yl)phenyl)acetamide (compound 1001), which was treated with concentrated hydrochloric acid (20 mL) and toluene (1 mL) and heated at 128 C. for 30 min. Evaporation of the volatiles gave a residue, to which saturated sodium bicarbonate was added. The resulting mixture was extracted with dichloromethane (3¡Á). Concentration of the organics and purification of the residue via silica gel chromatography (50 to 80% EtOAc/hexane) gave 2-(1H-pyrrolo[2,3-b]pyridin-4-yl)benzenamine (compound 1002, 1.07 g). To compound 1002 (14 mg) in methanol (1 mL) was added 4N HCl-dioxane (0.05 mL) and benzaldehyde (16 mg). The reaction mixture was capped and heated at 90 C. for 1 h. About 75% of the methanol was removed by evaporation, followed by the addition of ethyl ether (5 mL). The resulting solid was filtered and washed with ether (2¡Á) to yield compound 5 as the hydrochloride salt (22.5 mg)., 348640-06-2

As the paragraph descriping shows that 348640-06-2 is playing an increasingly important role.

Reference£º
Patent; Vertex Pharmaceuticals Incorporated; US2010/81645; (2010); 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

4264-35-1, 1-(1H-Indol-2-yl)ethanone is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4264-35-1

5-Chloro-2-hydroxy-N’-((1E)-1-(1H-indol-2-yl)ethylidene)benzohydrazide (6t) To a mixture of methyl 5-chloro-2-hydroxybenzoate (162 mg, 0.87 mmol) in isobutanol (0.5 mL) was added hydrazine hydrate (42 muL, 0.87 mmol). The reaction mixture was irradiated with microwaves for 15 min at 115 C. Isobutanol was added and the supernatant was removed. The residue was taken up in isobutanol (0.5 mL) and 1-(1H-indol-2-yl)ethanone 3p (138 mg, 0.87 mmol) was added. The reaction mixture was again irradiated with microwaves for 10 min at 110 C. The solid product was filtered and then, triturated with EtOH and Et2O to afford 6t as a yellow solid (90 mg, 33%). Mp = 198-200 C. 1H NMR (400 MHz, DMSO-d6): delta 12.46 (s, 1H), 11.39 (s, 1H), 10.07 (s, 1H), 7.86 (d, J = 2.4 Hz, 1H), 7.60 (d, J = 7.6 Hz, 1H), 7.47 (d, J = 7.6 Hz, 1H), 7.41 (dd, J = 8.8 Hz, 2.4 Hz, 1H), 7.19 (tm, J = 7.6 Hz), 7.03 (m, 2H), 6.93 (d, J = 8.8 Hz, 1H), 2.48 (s, 3H). 13C NMR (100 MHz, DMSO-d6): delta 158.0, 153.8, 137.5, 136.5, 132.8, 127.7, 126.8, 123.4, 122.3, 120.9, 119.3, 119.1, 111.8, 104.9, 14.5. HRMS calcd for (C17H1435ClN3O2+Na)+ 350.0663, found 350.0667.

4264-35-1 1-(1H-Indol-2-yl)ethanone 589081, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Article; Kumar, Nag S.; Amandoron, Emily A.; Cherkasov, Artem; Brett Finlay; Gong, Huansheng; Jackson, Linda; Kaur, Sukhbir; Lian, Tian; Moreau, Anne; Labriere, Christophe; Reiner, Neil E.; See, Raymond H.; Strynadka, Natalie C.; Thorson, Lisa; Wong, Edwin W.Y.; Worrall, Liam; Zoraghi, Roya; Young, Robert N.; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7069 – 7082;,
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