Category: 387-43-9

Downstream synthetic route of 387-43-9

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.387-43-9,4-Fluoroindole,as a common compound, the synthetic route is as follows.

To a solution DMF (0.670 ml8.653 mmol) in dichloromethane (2.5 mL) cooled to -15 ¡ãC was added dropwise phosphorus oxychloride (0.400 mL; 4.291 mmol). After 15 min at -15 ¡ãC, a solution of 4-fluoro-1 /-/-indole (0.500 g; 3.700 mmol) in dichloromethane (2 mL) was added. The reaction mixture was allowed to warm to room temperature and was stirred at room temperature overnight. A saturated sodium bicarbonate solution was added and the reaction mixture was extracted with dichloromethane. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using ethyl acetate (50percent) in heptane as eluent furnished 0.144 g (24percent) of 4-fluoro- 1 H-indole-3-carbaldehyde as a beige solid. ESI/APCI(+): 164. ESI/APCI(-): 162 (M-H).

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Reference£º
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim; WO2013/45516; (2013); 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

Analyzing the synthesis route of 387-43-9

387-43-9, As the paragraph descriping shows that 387-43-9 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.387-43-9,4-Fluoroindole,as a common compound, the synthetic route is as follows.

Take 135 mg (1 mmol) of 4-fluoroindole, 132.6 mg (1.3 mmol) of 5-hydroxy-2-pentanone and 20.48 mg (0.04 mmol) of tris(pentafluorophenyl)boron in a 10 mL reaction tube. The reaction was stirred at 40 C, and monitored by TLC until hydrazine disappeared, extracted with 3¡Á20 mL ethyl acetate, and the organic phase was washed with saturated brine.The organic layer was dried over anhydrous sodium sulfate, and the solvent ethyl acetate was evaporated to dryness (methanol ethyl ether: 20:1) to afford 3-(tetrahydro-2-methyl-2-furanyl)-4-fluoro-1H-indole product 175 mg, yield: 80%.

387-43-9, As the paragraph descriping shows that 387-43-9 is playing an increasingly important role.

Reference£º
Patent; Huazhong University of Science and Technology; Wang Shijun; Xia Sang; Tang Xiangying; (18 pag.)CN109912579; (2019); 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

Brief introduction of 387-43-9

As the paragraph descriping shows that 387-43-9 is playing an increasingly important role.

387-43-9, 4-Fluoroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 4-fluoro-1H-indole (1.0 g, 7.400 mmol) and TFA (5.667 mL, 74.00 mmol) in CH2C12(25 mL) was added triethylsilane (3.546 mL, 22.20 mmol). The reaction was stirred at 23 ¡ãC for 15 h before quenched with saturated NaHC03. The mixture was extracted with DCM. The organic extract was concentrated. The residue was purified by preparative HPLC to give the title compound (0.15 g). LCMS m/z = 137.8 [M+H]+., 387-43-9

As the paragraph descriping shows that 387-43-9 is playing an increasingly important role.

Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (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

Brief introduction of 387-43-9

387-43-9, The synthetic route of 387-43-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.387-43-9,4-Fluoroindole,as a common compound, the synthetic route is as follows.

Synthesis of 4-fluoro-1H-indole-3-carbaldehyde (Intermediate-23) To a 25 mL RB flask fitted with magnetic stirrer were added DMF (0.413 g) and POCl3 (0.623 g, 4 mmol) at 0¡ã C. under N2 atmosphere and the resulting mixture was stirred for 30 minutes at same temperature. Then Starting Material-4 (500 mg, 3.7 mmol) in DMF was added to the mixture and stirred at 40¡ã C. for 1 hour. After completion of the reaction the reaction mixture was cooled to 0¡ã C., quenched with NaOH solution and was extracted with ethyl acetate. Organic layers were concentrated to give crude material, which was then purified by silica-gel column chromatography eluting with hexane:EtOAc to give Intermediate-23 (230 mg) as brown material. LC-MS (M+H)+=164.2.

387-43-9, The synthetic route of 387-43-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Rao, Jagannath Madanahalli Ranganath; Venkatesham, Uppala; Doppalapudi, Sivanageswara Rao; Kenchegowda, Bommegowda Yadaganahalli; Fernand, George; George, Jenson; Madhavan, G R; Naidu, Gorle Paidapu; Kadambari, V. S. Naga Rajesh; Jagannath, S; Manivannan, R; Kumar, T Senthil; Kumar, B Siva Senthil; Mallikarjuna, Rayi; US2015/141650; (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

Simple exploration of 387-43-9

387-43-9, 387-43-9 4-Fluoroindole 2774502, aindole-building-block compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.387-43-9,4-Fluoroindole,as a common compound, the synthetic route is as follows.

To a solution of 4-fluoro-lH-indole (150 g, l . l lmol) and DMAP (4.5 g, 3percentWt) in THF (2.5 L) was added (Boc)20 (255 g, 1.16 mol) dropwise. The mixture was stirred at room temperature overnight. The organic solvent was removed in vacuum, and the residue was purified by column chromatography (PE) to give tert-butyl 4-fluoro-lH-indole-l-carboxylate (250 g, yield: 96percent). 1H- MR (CDC13, 400 MHz) delta 7.92 (d, J= 8.4 Hz, 1H), 7.55 (d, J= 3.6 Hz, 1H), 7.23 (m, 1H), 6.90 (m, 1H), 6.66 (d, J = 3.6 Hz, 1H), 1.67 (s, 9H). MS (M+H)+: 236.

387-43-9, 387-43-9 4-Fluoroindole 2774502, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; HE, Shuwen; DAI, Xing; PALANI, Anandan; NARGUND, Ravi; LAI, Zhong; ZORN, Nicolas; XIAO, Dong; DANG, Qun; LI, Peng; PENG, Xuanjia; SOLL, Richard; WO2014/121418; (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

Analyzing the synthesis route of 387-43-9

387-43-9, The synthetic route of 387-43-9 has been constantly updated, and we look forward to future research findings.

387-43-9, 4-Fluoroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 10-Synthesis of tert-butyl 4-fluoro-1H-indole-1-carboxylate To a solution of 4-fluoro-1H-indole (5 g, 0.11 mol) and DMAP (150 mg, 3percent Wt) in THF (50 mL) was added (Boc)2O (8.5 g, 0.04 mol) dropwise. The mixture was stirred at room temperature for 2 hours. The organic solvent was removed in vacuo, and the resulting residue was purified using column chromatography (pure petroleum ether) to provide tert-butyl 4-fluoro-1H-indole-1-carboxylate (8.3 g, yield: 96percent). 1H-NMR (CDCl3, 400 MHz) delta 7.92 (d, J=8.4 Hz, 1H), 7.55 (d, J=3.6 Hz, 1H), 7.23 (m, 1H), 6.90 (m, 1H), 6.66 (d, J=3.6 Hz, 1H), 1.67 (s, 9H). MS (M+H)+: 236.

387-43-9, The synthetic route of 387-43-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Liverton, Nigel J.; McComas, Casey Cameron; Habermann, Joerg; Koch, Uwe; Narjes, Frank; Li, Peng; Peng, Xuanjia; Soll, Richard; Wu, Hao; Palani, Anandan; He, Shuwen; Dai, Xing; Liu, Hong; Lai, Zhong; London, Clare; Xiao, Dong; Zorn, Nicolas; Nargund, Ravi; US2014/213571; (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

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387-43-9, The synthetic route of 387-43-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.387-43-9,4-Fluoroindole,as a common compound, the synthetic route is as follows.

4-fluoro-2, 3-dih vdro- 1 H-indoleTo a stirred solution of 4-fluoro-1 H-indole (950 mg, 7.03 mmol) in Acetic Acid (20 mL) at 12 ¡ãC under nitrogen was added sodium cyanoborohydride (1458 mg, 23.20 mmol) portionwise. The reaction was stirred at 12 ¡ãC for 2 hours, and at room temperature overnight. The reaction was worked up by pouring into sodium hydroxide (10 N). The aqueous was extracted with diethyl ether (3 x 100 mL), and the combined organics dried over sodium sulfate. LCMS analysis at this point indicated presence of product and some acylated product, along with some acylated starting material. The crude was dissolved in THF (10 mL) and treated with NaOH (6 N, 2 mL), then stirred at r.t. for 2 h. The reaction was stirred overnight, but no change in LCMS was observed, so the organic layer was removed, and the aqueous extracted with diethyl ether (2 x 10 mL), the combined organics were dried over sodium sulfate. The dried solution was filtered and concentrated, and the residue was purified by flash chromatography (0-25percent EtOAc in hexanes, 24-g silica gel column) to afford 4-fluoro-2,3-dihydro-1 H-indole (510 mg, 3.72 mmol, 52.9 percent yield) as a colorless oil. LC-MS(ES) m/z = 138 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 2.94 (t, J = 8.59 Hz, 2 H), 3.48 (t, J = 8.59 Hz, 2 H), 5.79 (br. s., 1 H), 6.23 – 6.35 (m, 2 H), 6.87 – 6.99 (m, 1 H).

387-43-9, The synthetic route of 387-43-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (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

Brief introduction of 387-43-9

The synthetic route of 387-43-9 has been constantly updated, and we look forward to future research findings.

387-43-9, 4-Fluoroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 4-fluoro-1H-indole (150 g, 1.llmol) and DMAP (4.5 g, 3%Wt)in THF (2.5 L) was added (Boc)20 (255 g, 1.16 mol) dropwise. The mixture was stirred at roomtemperature overnight. The organic solvent was removed in vacuum, and the residue was purified by column chromatography (PE) to give tert-butyl 4-fluoro-1H-indole-1-carboxylate (250 g, yield: 96%). ?H-NMR (CDC13, 400 MHz) 7.92 (d, J= 8.4 Hz, 1H), 7.55 (d, J 3.6 Hz, 1H), 7.23 (m, 1H), 6.90 (m, 1H), 6.66 (d, J= 3.6 Hz, 1H), 1.67 (s, 9H). MS (M+H): 236.

The synthetic route of 387-43-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda, L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/123793; (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

New learning discoveries about 387-43-9

As the paragraph descriping shows that 387-43-9 is playing an increasingly important role.

387-43-9, 4-Fluoroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: Preparation of 4-fluoro-1-tosyl-1H-indole (F-1) [0329] To a flask was added 4-fluoro-1H-indole (1000 mg, 7.40 mmol), sodium hydride (326 mg, 8.14 mmol), and DMF (14.8 mL). The solution was allowed to stir at room temperature for 30 min. 4-methylbenzene-1-sulfonyl chloride (2116 mg, 11.10 mmol) was then added to the flask and the resulting solution was allowed to stir for 3 hours. The mixture was diluted with ethyl acetate, washed 2¡Á with aqueous sodium hydrogen carbonate and 1¡Á with brine. The combined aqueous layer was back extracted once with ethyl acetate, combined organic layers were dried with Na2SO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography (EtOAc/Hexane 0-75percent) to give the desired product as a colorless solid. (1.76 g, 82percent) LCMS (ESI) calc’d for C15H12FNO2S [M+H]+: 290. found: 290. .

As the paragraph descriping shows that 387-43-9 is playing an increasingly important role.

Reference£º
Patent; Barr, Kenneth J.; Maclean, John K.; Zhang, Hongjun; Beresis, Richard T.; Zhang, Dongshan; Andresen, Brian M.; Anthony, Neville J.; Lapointe, Blair T.; Sciammetta, Nunzio; US2015/191434; (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

Analyzing the synthesis route of 387-43-9

The synthetic route of 387-43-9 has been constantly updated, and we look forward to future research findings.

387-43-9, 4-Fluoroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To the 10 ml Schlenk tube containing the substrate indole 1a (0.25 mmol, 30 mg), 4-chloroaniline 2a (0.75 mmol, 96 mg) and acetonitrile (4 ml) was added 1-fluo-1,2-benziodoxol-3-(1H)-one (0.89 mmol, 237 mg), the mixture was stirred at room temperature as monitored by TLC. The solution was then quench by NaHCO3 solution and extracted with EtOAc, the combined organic layers were dried over Na2SO4, filtered, and evaporated under vaccum, the residue was purified by column chromatography (eluents: n-hexane/ethyl acetate = 50/1 v/v) on silica gel to afford the desired product 3a.

The synthetic route of 387-43-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Jiang, Xinpeng; Li, Guizhou; Yu, Chuanming; Tetrahedron Letters; vol. 59; 15; (2018); p. 1506 – 1510;,
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