Month: September 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.221352-46-1,2-(tert-Butoxycarbonyl)isoindoline-1-carboxylic acid,as a common compound, the synthetic route is as follows.

To a solution of 2,3-dihydro-isoindole-1,2-dicarboxylic acid 2-tert-butyl ester (344 mg, CAS 221352-46-1), 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one (265 mg; CAS 536747-52-1) and DIPEA (0.34 ml) in 10 ml acetonitrile and 1 ml DMF was added BOP-Cl (382 mg). The reaction mixture was stirred for 24 hrs at rt, diluted with AcOEt and washed with 1M HCl, 1M NaOH and brine. The organic layers were dried over magnesium sulfate, evaporated and purified by chromatography (silica gel; AcOEt) to deliver the title compound as a yellow oil (280 mg). MS: 450.4 (M+H)+., 221352-46-1

The synthetic route of 221352-46-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Boehringer, Markus; Zbinden, Katrin Groebke; Haap, Wolfgang; Panday, Narendra; Ricklin, Fabienne; Stahl, Martin; Schmitz, Petra; US2007/112012; (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

399-68-8, 4-Fluoro-1H-indole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3 To a solution of 34 (179 mg, 1.00 mmol) in anhydrous DMF (2.0 mL) were added NH4Cl (160 mg, 3.00 mmol), EDCI (395 mg, 2.20 mmol), HOBt (297 mg, 2.20 mmol) and TEA (303 mg, 3.00 mmol) at RT. After stirring at RT for 3 h, the mixture was quenched with H2O (10 mL) the resulting mixture was extracted with EtOAc (3*6 mL). The combined extracts were dried and concentrated. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (5:1 to 3:1) to afford 130 mg (73%) of 4-fluoro-1H-indole-2-carboxamide (36) as a white solid. LCMS (ESI) m/z: 179.1 [M+H]+., 399-68-8

The synthetic route of 399-68-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Genentech, Inc.; Array BioPharma Inc.; Blake, Jim; Chen, Huifen; Chicarelli, Mark; Gaudino, John; Gazzard, Lewis; Kintz, Sam; Mohr, Pete; Robarge, Kirk; Schwarz, Jacob; Zhou, Aihe; US2014/66453; (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.52415-29-9,6-Bromoindole,as a common compound, the synthetic route is as follows.

52415-29-9, To a stirred suspension of 60% sodium hydride (4.88 g, 122 mmol) in tetrahydrofuran (1 50 mL) was added 6-bromoindole (1 5.0 g, 76.5 mmol) portionwise, followed by methyl iodide (1 1.9 g, 83.8 mmol) dropwise and the mixture stirred at room temperature for 16 h. After this time, the reaction was poured into ice-cold water and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed sequentially with water, then brine and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate concentrated under reduced pressure to afford 6-bromo-l -methyl -1 H-indole as a pale red solid: NMR (400 MHz, CDC13) d 7.49 (m, 2H), 7.22 (dd, J = 8.0, 1.6 Hz, 1 H), 7.04 (d, J = 3.2 Hz, 1 H), 6.47 (d, J = 3.2 Hz, 1 H), 3.77 (s, 3H).

The synthetic route of 52415-29-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GILEAD SCIENCES, INC.; BLOMGREN, Peter; CURRIE, Kevin, S; KROPF, Jeffrey, E.; LEE, Seung, H.; MITCHELL, Scott, A.; SCHMITT, Aaron, C.; XU, Jianjun; ZHAO, Zhongdong; WO2011/112995; (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

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

50820-65-0,50820-65-0, Methyl 1H-indole-6-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of compound 26 (2 g, 11.4 mmol) and cyclohexanone (3.36 g,34.2 mmol) in MeOH (15 mL), aqueous KOH (1.92 g, 34.2 mmol, dissolved in 13 mL water) was added. The resulting reaction mixture was stirred at 75 ¡ãC for 18 h. The progress of the reaction was monitored by LCMS. After completion, the reaction mixture was concentrated in vacuo. The residue was diluted with water, acidified with acetic acid pH?6; the obtained solidwas filtered; washed with water and dried in vacuo to afford the crude. The crude compound was triturated with IPA to afford compound 34 (1.6 g, 58percent) as light brown solid. ?H-NMR (400 MHz, DMSO-d6): oe 11.33 (s, 1H), 7.97 (s, 1H), 7.75 (d, J= 8.0 Hz, 1H), 7.61 (d, J= 8.4 Hz, 1H), 7.47 (s, 1H), 6.19 (s, 1H), 2.42 ?2.39 (m, 2H), 2.22 ? 2.20 (m, 2H), 1.76 – 1.72 (m, 4H). LCMS observed (m/z): 242 (M+1).

As the paragraph descriping shows that 50820-65-0 is playing an increasingly important role.

Reference£º
Patent; ASSEMBLY BIOSCIENCES, INC.; TURNER, William; ARNOLD, Lee, Daniel; LI, Leping; BURES, Mark; HAYDAR, Simon; MAAG, Hans; BANNEN, Lynne; (176 pag.)WO2018/53157; (2018); 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

436091-59-7, 4-Bromo-7-methoxy-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2:A solution of indole 52b (619 mg, 2.7 mmol) in DMF (5 mL) at 230C is treated with NaH (60% in oil dispersion, 125 mg, 5.2 mmol) and stirred at 230C for 5 min. Ethyl bromoacetate (637 muL, 5.75 mmol) is added and the solution is stirred at 230C for 24 h; UPLC/MS analysis indicated 62 % conversion. To this mixture, additional amounts of NaH (60% in oil dispersion, 77 mg, 1.9 mmol) and ethyl bromoacetate (244 muL, 2.2 mmol) are added. After 10 min, the UPLC analysis indicated > 90% conversion. The reaction is diluted with EtOAc, washed with saturated NH4CI solution and brine (4X), dried over MgSO4, filtrated, concentrated and purified by flash chromatography (5-20 %; EtOAc/hexanes) to give 52c (541 mg, 63 % yield) as a yellow oil., 436091-59-7

Big data shows that 436091-59-7 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; WO2009/62285; (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

1075-34-9, 5-Bromo-2-methylindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-bromo-2-methyl-1H-indole (0.5 g, 2.38 mmol) was dissolved in anhydrous toluene (50 mL) and Pd(PPh3)4 (0.12 g, 0.11 mmol) was added. The resulting solution was allowed to stir for 30 min under nitrogen flow. 3-Thiopheneboronic acid (0.45 g, 3.57 mmol) was dissolved in 15 mL absolute ethanol and added to the reaction, followed by saturated 25 mL aqueous NaHCO3. The reaction mixture was heated to reflux overnight. The solvent was evaporated and the residue was dissolved in water and ethyl acetate. The organic portion was dried (MgSO4) and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel (isooctane/ethyl acetate, gradient) to give the title compound in 84% yield (0.42 g, 1.96 mmol). MS m/z (relative intensity, 70 eV) 213 (M+, bp), 212 (73),167 (9),139 (4),106(8). 1H NMR (CDCl3, 300 MHz) delta: 2.38 (s, 3H), 6.21 (s, 1H), 7.22 (d,J = 8.23 Hz, 1H), 7.35 (dd, J = 6.30, 0.76, 2H), 7.38-7.46 (m, 1H), 7.72(s, 2H). 13C NMR (CDCl3, 75 MHz) delta: 13.65, 100.70, 110.38, 117.47,118.53, 120.18, 125.61, 126.79, 127.96, 129.52, 135.45, 135.77, 143.81.

1075-34-9, The synthetic route of 1075-34-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Mattsson, Cecilia; Svensson, Peder; Boettcher, Henning; Sonesson, Clas; European Journal of Medicinal Chemistry; vol. 63; (2013); p. 578 – 588;,
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

74420-02-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.74420-02-3,4-Hydroxy-7-azaindole,as a common compound, the synthetic route is as follows.

To a solution of compound lH-pyrrolo[2,3-]pyridin-4-ol (0.1 mmol, 13.4 mg, prepared generally according to the procedures outlined by Thibault, C. et al.Org. Lett. 2003, 5, 5023-5025, the disclosure of which is incorporated by reference, in DMF (1 mL) was added cesium carbonate (Aldrich, 0.25 mmol, 81 mg). The mixture was stirred at room temperature for 0.5 h. To this mixture was added 2,4,5-trifluoro- iV-(l-(4-fluorophenyl)-2-oxo-l,2-dihydropyridin-3-yl)beiizamide (36 mg, 0.1 mmol). The reaction mixture was heated at 60 0C for 8 h. After the reaction mixture was cooled to room temperature, 2 mL of cold water was added. The reaction mixture was extracted with EtOAc (3 x 20 mL). The organic extracts were dried with MgSO4, concentrated in vacuo, and purified by preparative HPLC. The desired fractions were combined, concentrated in vacuo, and lyophilized to dry to give the title compound (trifluoroacetic acid salt, 10.0 mg, 21percent yield) as a white solid. 1H NMR (CD3OD) delta 8.61 (d, IH, J= 5.7 Hz), 8.26 (d, IH, J= 6.6 Hz), 8.02 (dd, IH, J= 11.0, 6.6 Hz), 7.51 (d, IH, J= 3.9 Hz), 7.29-7.25 (m, 3H), 7.36 (d, IH, J= 6.6 Hz), 7.25 (t, 2H, J= 8.8 Hz), 6.90 (d, IH, J= 6.6 Hz), 6.60 (d, IH, J= 3.3 Hz), 6.50 (t, IH, J= 7.2 Hz); MS(ESI+) m/z All..22 (M + H)+.

74420-02-3 4-Hydroxy-7-azaindole 12646048, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/35428; (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

272-49-1, 4-Azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 118; 2-(3-Fluoro-phenyl)-pyrimidine-5-carboxyric acid pyrrolor3,2-b1pyridin-l-vlamide; Step 1 : A solution of pyrrolo[3,2-b]pyridine (1.64 mmol) and potassium tert-butoxide (3.29 mmol) in DMF (7.3 mL) is stirred at rt under N2 for 2 h. 0.15 M NH2CLm ether (16.3 mL) is added drop-wise at rt and the reaction mixture is stirred at rt for 3 h. The reaction mixture is quenched with 5 percent Na2S2O3 aqueous solution (10 mL), and extracted with ether. The combined organic layer is washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with EtOAc to afford pyrrolon .2-blpyridin- 1 -ylamine (136 mg, 62percent) as a solid. MS: 134 (M+H); 1H NMR (300 MHz, CDCl3): delta 4.89 (br, 2N-H), 6.61 (d, H), 7.16 (m, H), 7.38 (d, H), 7.76 (d, H), 8.47 (d, H)., 272-49-1

272-49-1 4-Azaindole 9226, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; SANOFI-AVENTIS; WO2008/121670; (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

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