Indole Building Blocks

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4837-90-5,4-Methoxy-1H-indole,as a common compound, the synthetic route is as follows.

A. 1-Benzyl-4-methoxyindole NaH (7.7 g, 191.7 mmol) was added portionwise to a 0 C solution of 4-methoxyindole (21.7 g, 147 mmol) in 750 mL of anhydrous DMF. After 15 min, the slurry was treated with benzyl bromide (17.5 mL, 147 mmol). The reaction mixture was allowed to warm to ambient temperature and stir overnight. The reaction mixture was poured into 1 L of H2O. The layers were separated, and the aqueous phase was extracted with EtOAc (2 X 200 mL). The combined organic layers were washed with H2O (4 x 500 mL), dried over Na2SO4, filtered and concentrated in vacuo.The crude residue was purified by flash chromatography (SiO2; hexanes) to give 32.9 g (138.6 mmol; 94%) of the title compound as a white solid. Electrospray MS 238 (M+1);

4837-90-5, As the paragraph descriping shows that 4837-90-5 is playing an increasingly important role.

Reference£º
Patent; ELI LILLY AND COMPANY; EP950661; (1999); 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

882679-96-1,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.882679-96-1,Methyl 4-bromo-1H-indole-6-carboxylate,as a common compound, the synthetic route is as follows.

Step a. To a solution of methyl 4-bromo-lH-indole-6-carboxylate (CAS Number 882679-96-1) (1.0 g, 3.95 mmol) in TFA (5 ml) was added triethylsilane (1.9 ml, 11.86 mmol) at rt. The reaction mixture was stirred at 60C for 45 min. The resulting reaction mixture was cooled to rt, poured into saturated NaHC03 solution (50 ml) extracted with EtOAc (3 x 30 ml). The combined organic layer was dried over Na2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (10% EtOAc in hexane) yielding methyl 4-bromoindoline-6-carboxylate (0.75 g, 29.4 mmol). LCMS: Method C, 2.31 min, MS: ES+ 256.3, 258.3; NMR (400 MHz, DMSO-d6) delta ppm 7.20 (d, J= 1.2 Hz, 1H), 6.94 (d, J=1.6 Hz, 1H), 6.19 (s, 1H), 3.80 (s, 3H), 3.54 (t, J=8.8 Hz, 2H), 2.97 (t, J=8.8 Hz, 2H).

The synthetic route of 882679-96-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MISSION THERAPEUTICS LIMITED; KEMP, Mark; STOCKLEY, Martin; JONES, Alison; (138 pag.)WO2017/9650; (2017); 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.24621-73-6,4-Chloro-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.,24621-73-6

Step 1. 4-Chloro-N-methoxy-N-methyl-1H-indole-2-carboxamide A mixture of 4-chloro-1H-indole-2-carboxylic acid (from Ryan Scientific, 1.0 g, 5.1 mmol), O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (2.9 g, 7.7 mmol) and triethylamine (3.6 mL, 26 mmol) in N,N-dimethylformamide (15 mL) was stirred at room temperature for 10 minutes. N,O-Dimethylhydroxylamine hydrochloride (0.75 g, 7.7 mmol) was added and the resulting suspension was stirred at room temperature overnight. The mixture was quenched with water and then extracted with EtOAc. The combined organic layers were dried over MgSO4, concentrated and purified on silica gel (eluting with 0-35% EtOAc in hexane) to give the desired product (0.35 g, 29%). LCMS calculated for C11H12ClN2O2(M+H)+: m/z=239.1; Found: 239.1.

24621-73-6 4-Chloro-1H-indole-2-carboxylic acid 90561, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Li, Yun-Long; Combs, Andrew P.; US2011/312979; (2011); 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.348640-06-2,4-Bromo-7-azaindole,as a common compound, the synthetic route is as follows.

c.HNO3 (0.93 mL) was added drop wise to a solution of a H2SO4 (0.64 mL) at 0 C. 4-Bromo-1H-pyrrolo[2,3-b]pyridine (2 g, 10.15 mmol) in c.H2SO4 (9 mL) was added slowly, keeping the temperature at 0 C. After addition the reaction was stirred for a further hour at 0 C. before pouring carefully onto rapidly stirring ice/H2O (100 mL). The suspension was stirred for 30 mins and then the solids separated via filtration. The filter cake was washed with copious amounts of H2O before drying in vacuo at 40 C., to afford the desired compound, 1.9 g, 77.3%

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

Reference£º
Patent; Vernalis (R&D) Limited; Stokes, Stephen; Graham, Christopher John; Ray, Stuart Christopher; Stefaniak, Emma Jane; US2015/11533; (2015); 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.1477-49-2,3-Indoleglyoxylic Acid,as a common compound, the synthetic route is as follows.

The reagents used for each of the amide bond formation was amino core (4 mumol), carboxylic acid (4 mumol, 1 eq.), DIEA (5 mumol, 1.2 eq.) and HBTU (4.5 mumol, 1.1eq.). A stock of the amino core for synthesis of 102 members requires an amount in excess of 150 fold. Both the starting amino core and the carboxylic acids were prepared as a stock solution of DMSO in a concentration of 0.6 mmol/1500 muL and 4 mumol/10 muL, respectively. HBTU and DIEA were dissolved in DMSO as a concentration of 4.5 mumol/10 muL (V/V) and 5 mumol/10 muL (V/V), respectively. Each of the acid portion was firstly mixed with the solution of HBTU in a plastic tube for 30 sec, followed by the addition of a mixture of the solution of amino core (4 mumol, 10 muL) and DIEA (10 muL) in a total volume of 40 muL. All vials were shaken for 1 min ultrasonically for the subsequent series dilution., 1477-49-2

The synthetic route of 1477-49-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Su, Yuan-Hsiao; Chiang, Li-Wu; Jeng, Kee-Ching; Huang, Ho-Lien; Chen, Jenn-Tzong; Lin, Wuu-Jyh; Huang, Chia-Wen; Yu, Chung-Shan; Bioorganic and Medicinal Chemistry Letters; vol. 21; 5; (2011); p. 1320 – 1324;,
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

913836-24-5, tert-Butyl 4-nitro-1H-indole-1-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,913836-24-5

To a stirred solution of 1-Boc-4-nitroindole (6.14 g, 23.4 mmol) in EtOH (100 mL) was added 10% Pd/C (614 mg) under N2. The resulting mixture was shaken under hydrogen (H2, 50 psi) at room temperature for 8 h. The mixture was filtered through a pad of Celite, and washed with EtOH. The filtrate was concentrated under reduced pressure to give the product 1-Boc-4-aminoindole as off-white solid (5.23 g, 96% yield). MS (ESI) m/z 233.2

913836-24-5 tert-Butyl 4-nitro-1H-indole-1-carboxylate 25307166, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Wyeth; US2009/227575; (2009); 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.6960-46-9,Ethyl 7-nitro-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.,6960-46-9

Preparation 29: Synthesis of 7-(tetrahydro-pyran-4-ylamino)-1H-indole-2-carboxylic acidEthyl 7-nitroindole-2-carboxylate (2.5 g, 10.7 mmol) was dissolved in methanol (50 ml). 10% Pd/C (200 mg) was added, and the mixture was stirred for 1 h under hydrogen gas. The mixture was filtered through celite, and the filtrate was distilled under reduced pressure. The distillate was dissolved 1,2-dichloroethane (50 ml), and tetrahydro-4H-pyran-4-one (1.3 ml, 12.8 mmol) and sodium triacetoxyborohydride (3.4 g, 16.1 mmol) were added. The mixture was stirred for 8 h at room temperature. After completion of the reaction, water was added. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure and concentrated. The residue was purified by column chromatography. Thus obtained compound was dissolved in methanol (50 ml) and tetrahydrofuran (50 ml), 1N-sodium hydroxide (43 ml, 42.8 mmol) was added, and the mixture was stirred for 8 h at room temperature. 1N-hydrochloric acid solution was added, and the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure to give the title compound (2.1 g, Yield 76%).1H-NMR (400 MHz, DMSO-d6); delta 12.87 (br s, 1H), 11.46 (s, 1H), 6.97 (d. J=2.0 Hz, 1H), 6.86 (d, J=1.6 Hz, 1H), 6.85 (s, 1H), 6.37 (m, 1H), 5.73 (br s, 1H), 3.90 (m, 2H), 3.61 (m, 1H), 3.50 (m, 2H), 2.00 (m, 2H), 1.48 (m, 2H)Mass spectrum (ESI, m/z): Calculated: 260.12, Found: 260.30

The synthetic route of 6960-46-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Kim, Soon Ha; Kim, Hyoung Jin; Chung, Chul Woong; Park, Heui Sul; Kwak, Hyo Shin; Kim, Sung Ho; Park, Jin Gu; US2010/291533; (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

4769-96-4, 6-Nitro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[000423j To a stirred solution of compound 1 (1 g, 1 eq) in DMF (10 mL), NaH (0.22 1 g,1.5 eq) was added at 0 C followed by the addition of methyl iodide (2.3 mL, 3 eq) at same temperature. The reaction mixture was stirred at same temperature for 30 mm. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate (3 X 25 mL). Combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 20% EtOAc-hexane to afford the title compound 2.

4769-96-4, As the paragraph descriping shows that 4769-96-4 is playing an increasingly important role.

Reference£º
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); 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

387-44-0, 7-Fluoroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7-Fluoro-5-(piperazin-1-yl)-1H-indole To a mixture of 7-fluoro-1H-indole (18.5 g, 0.14 mol), borane trimethylamine complex (80 g, 1.1 mol) and 1,4-dioxane (700 mL) was, over a periode of 15 min, added a 37% aqueous HCl (80 mL) solution. The resulting solution reached a maximum temperature of 40 C., and the solution was subsequent stirred at room temperature for another 16 h. The mixture was boiled under reflux for 1 h, 6 M aqueous HCl (500 mL) was added, and the resuting mixture was boiled under reflux for another 15 min. The solution was concentrated at atmospheric pressure and poured onto a mixture of ice and brine. The aqueous phase was made alkaline by the use of 25% aqueous ammonia and extracted with ethyl acetate. The combined organic phase was dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in a mixture of triethylamine (38 mL, 0.27 mol) and tetrahydrofuran (350 mL) and cooled to 10 C. Acetyl Chloride (11.2 g, 0.14 mol) was added to the mixture, which thereafter was filtered and concentrated in vacuo. The residue was purified by flash chromatography (ethyl acetate/heptane 50:50) to give 1-(7-fluoro-2,3-dihydro-1H-indol-1-yl-ethanone (16.7 g, 0.09 mol), which was dissolved in acetic acid (250 mL). To this mixture was added 100% nitric acid (5.8 ml, 0.14 mol) over a period of 5 min, and the resulting mixture was stirred at room temperature for 2 h. The reaction was not run to completion, and an additional amount of 6 mL of 100% nitric acid was added. Another 6 mL of 100% nitric acid was added and the mixture was stirred at room temperature for 16 h. The mixture was poured onto a mixture of ice and brine. The aqueous phase was made alkaline by the use of 25% aqueous ammonia and extracted with ethyl acetate. The combined organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was crystallised from a mixture of ethyl acetate and 2-propanol to give 1-(7-fluoro-5-nitro-2,3-dihydro-1H-indol-1-yl)-ethanone (15.9 g), which was dissolved in methanol (500 mL). To this solution was added ammonium formate (44.4 g, 0.7 mol) and palladium (5 wt %, dry basis) on activated carbon (4.0 g), and the mixture was boiled under reflux for 30 min. The mixture was cooled in an ice bath, filtered and concentrated in vacuo. The residue was dissolved in methanol (100 mL) and ethyl acetate (500 mL), and ammonium formate precipitated out of solution and was removed by filtration. The mother liquor was concentrated in vacuo, and the residue was purified by flash chromatography (ethyl acetate/heptane 65:35) to give 1-(5-amino-7-fluoro-2,3-dihydro-1H-indol-1-yl)-ethanone (13.1 g, >91%). The compound was dissolved in methanol (350 mL), 28% aqueous sodium hydroxide (100 mL) and water (100 mL), and the resulting mixture was boiled under reflux for 4 h. The reaction mixture was concentrated to a volume of about 200 mL, and brine (1 L) was added. The aqueous phase was extracted with a mixture of ethyl acetate and tetrahydrofuran. The combined organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give 7-fluoro-2,3-dihydro-1H-indol-5-ylamine (11.0 g, 96%). This compound was dissolved in p-xylene (500 mL), and palladium (5 wt %, dry basis) on activated carbon (7.5 g) was added. The resulting mixture was boiled under reflux by the use of a Dean/Stark trap for 1.5 h, cooled and filtered. The filter cake was washed with ethyl acetate and tetrahydrofuran, and the organic phases were combined and concentrated in vacuo. The residue was purified by flash chromatography (ethyl acetate/heptane 50:50) to give 7-fluoro-1H-indol-5-ylamine (3.3 g, 29%). A further batch of 7-fluoro-1H-indol-5-ylamine was prepared (0.2 g), and the combined batch was used in the following. A mixture of N-benzyliminodiacetic (5.9 g, 0.027 mol), 1,1′-carbonyldiimidazole (9.0 g, 0.056 mol) and tetrahydrofuran (175 mL) was boiled under reflux for 30 min. To this solution was added a solution of 7-fluoro-1H-indol-5-ylamine (3.47 g, 0.023 mol) in tetrahydrofuran (75 mL) over a period of 1 h. The resulting mixture was boiled under reflux for 3 h and concentrated in vacuo to 50 mL. This solution was purified by flash chromatography (ethyl acetate/heptane 80:20) to give 4-benzyl-1-(7-fluoro-1H-indol-5-yl)piperazine-2,6-dione (7.8 g, 95%), which was dissolved in tetrahydrofuran (75 mL) and subsequently added drop wise to a solution of alane in tetrahydrofuran over 60 min at 5-10 C. The resulting mixture was stirred at 7 C. for 30 min and then quenched by addition of water (6.5 mL), 15% aqueous sodium hydroxide (3.25 mL) and water (16 mL). MgSO4 was added to the mixture, which was filtered and concentrated in vacuo. The residue was purified by flash chromatography (ethyl acetate/heptane 50:50) to give 5-(4-benzylpiperazin-1-yl)-7-fluoro-1H-indole (4.9 g, 63%). The alane was prepared as described in the following: Lithium aluminium hydride (3.23 g, 0.085 mol) was suspended in tet…, 387-44-0

387-44-0 7-Fluoroindole 2774504, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Bang-Andersen, Benny; Larsen, Krestian; Mork, Niels; US2007/43058; (2007); 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

6146-52-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6146-52-7,5-Nitroindole,as a common compound, the synthetic route is as follows.

General procedure: To a solution of 1a-1b (4.5 mmol) in 4 mL ethanol was added80% hydrazine hydrate (2 mL) and 10% palladium charcoal (0.08g). The reaction was refluxed for 10 min and filtered by Celite.The filtrate was dried by sodium sulfate, and concentrated in vacuoto afford compounds 2a-2b, which were used without furtherpurification.

The synthetic route of 6146-52-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wang, Peng-Fei; Zhang, Yong-Jiao; Wang, Dong; Hu, Hui-Min; Wang, Zhong-Chang; Xu, Chen; Qiu, Han-Yue; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2372 – 2380;,
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