Tag: M.W:200-300

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.80360-20-9,1-(Phenylsulfonyl)-1H-indole-3-carbaldehyde,as a common compound, the synthetic route is as follows.

A solution of chlorotitanium (IV) triethoxide (22.5 g, 103 mmol, 1.05 equiv, Holoway, H. Chem. Ind. 1962, 3, 214) in dichloromethane (69 mL) was added via cannula to a solution of ethyl 2-((S,2S,5S)-2-hydroxypinan-3-imino)glybioncin C (E2-11, 24.8 g, 97.8 mmol, 1 equiv, (a) Oguri, T.; Kaway, N.; Yamada, S. Chem. Pharm. Bull. 1978, 26, 803. (b) Solladi-Cavallo, A.; Simon, M. C. Tetrahedron Lett. 1989, 30, 6011. (c) Solladi-Cavallo, A.; Simon-Wermeister, M. C.; Schwarz, J. Organometallics 1993, 12, 3743) in dichloromethane (300 mL) at 0 C. A fine powder of 1-(phenylsulfonyl)-1H-indole-3-carbaldehyde (E2-10, 29.3 g, 103 mmol, 1.05 equiv, Wenkert, E.; Moeller, P. D. R.; Piettre, S. R. J. Am. Chem. Soc. 1988, 110, 7188) was then added as a solid to the reaction mixture. Triethylamine (27.3 mL, 196 mmol, 2.00 equiv) was subsequently added dropwise via syringe and the reaction mixture was stirred at 0 C. After 21 h, brine (1 L) at 0 C. was added to the reaction mixture and the resulting bilayer suspension was filtered through Celite. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (2¡Á300 mL). The combined organic layers were dried over anhydrous sodium sulfate, were filtered, and were concentrated under reduced pressure. The resulting orange foam was purified by flash column chromatography on silica gel (eluent: gradient, 30?50% ethyl acetate in hexanes) to provide an inseparable mixture of diastereomeric aldol products (42.5 g, 80.6%) as a yellow foam. In some embodiments, the aldol products were highly prone to degradation through a retro-aldol pathway; thus, the mixture of diastereomers was quickly isolated and immediately used in the subsequent reaction. Structural assignments were made using additional information from gCOSY, HSQC, and gHMBC experiments. (1135) 1H NMR (600 MHz, CDCl3, 20 C.; only the peaks corresponding to the major diastereomer are tabulated): delta 7.96 (d, J=8.3, 1H, C8H), 7.86 (d, J=8.6, 2H, SO2Ph-o-H), 7.71 (s, 1H, C2H), 7.67 (d, J=7.8, 1H, C8H), 7.49 (t, J=7.6, 1H, SO2Ph-p-H), 7.39 (app-t, J=8.1, 2H, SO2Ph-m-H), 7.29 (app-t, J=7.3, 1H, C7H), 7.23 (app-t, J=7.2, 1H, C6H), 5.49 (d, J=6.9, 1H, C12H), 4.46 (d, J=6.9, 1H, C11H), 4.11-3.99 (m, 2H, CO2CH2CH3), 3.90 (br-s, 1H, C12OH), 2.42 (dd, J=2.0, 17.7, 1H, C16Ha), 2.19 (dd, J=2.7, 18.0, 1H, C16Hb), 2.11-2.05 (m, 1H, C18Ha), 2.00 (br-s, 1H, C20OH), 1.89 (app-t, J=5.8, 1H, C19H), 1.87-1.83 (m, 1H, C17H), 1.42 (s, 3H, C24H), 1.23 (s, 3H, C22/23H), 1.06 (app-t, J=7.4, 3H, CO2CH2CH3), 1.02 (d, J=4.7, 1H, C18Hb), 0.80 (s, 3H, C22/23H). 13C NMR (150 MHz, CDCl3, 20 C.): delta 180.6 (C15), 169.5 (C13), 138.0 (SO2Ph-ipso-C), 134.5 (C9), 133.6 (SO2Ph-p-C), 129.9 (C4), 129.2 (SO2Ph-m-C), 126.7 (SO2Ph-o-C), 124.9 (C7), 124.7 (C2), 123.1 (C6), 122.3 (C3), 120.2 (C5), 113.5 (C8), 76.8 (C20), 67.7 (C12), 67.4 (C11), 61.1 (CO2CH2CH3), 50.3 (C19), 38.5 (C21), 38.2 (C17), 33.8 (C16), 28.1 (C24), 27.8 (C18), 27.1 (C22/23), 22.6 (C22/23), 13.7 (CO2CH2CH3). FTIR (thin film) cm-1: 3422 (br-m), 2926 (s), 1734 (s), 1649 (m), 1557 (w), 1448 (s), 1373 (s), 1273 (m), 1181 (s), 1126 (m), 1089 (m), 1022 (w), 978 (w), 920 (w), 751 (m). HRMS (ESI) (m/z): calc’d for C29H35N2O6S [M+H]+: 539.2210. found: 539.2198. TLC (50% ethyl acetate in hexanes), Rf: 0.49 (UV, CAM, KMnO4).

80360-20-9, As the paragraph descriping shows that 80360-20-9 is playing an increasingly important role.

Reference£º
Patent; Massachusetts Institute of Technology; The Board of Trustees of the University of Illinois; Movassaghi, Mohammad; Kim, Justin; Hergenrother, Paul J.; Morrison, Karen; Boyer, Nicolas; (186 pag.)US9353150; (2016); B2;,
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.90271-86-6,5-Bromo-3-cyanoindole,as a common compound, the synthetic route is as follows.

90271-86-6, To a solution of 5-bromo-3-cyanoindole (2.0 g) in N,N-dimethylformamide (50 mL) were added cesium carbonate (7.4 g) and 4-fluorobenzoic acid ethyl ester (3.0 g), and this mixture was stirred at 80C for 48 hours. This reaction mixture was poured into water, and the precipitated solid was collected by filtration. This solid was washed with water, dried under reduced pressure at 50C to give the title compound (1.8 g).

As the paragraph descriping shows that 90271-86-6 is playing an increasingly important role.

Reference£º
Patent; Kissei Pharmaceutical Co., Ltd.; EP2133332; (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.16732-57-3,Ethyl 5-nitro-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.

Commercially available ethyl 5-nitro-1H-indole-2-carboxylate (1.00 g, 4.27 mmol) of methanol (20 mL) solution Palladium-carbon (907 mg) in addition, stirred for three hours under a hydrogen atmosphere. Celite filtration reaction and be evaporated and the residue that obtained the title compound (876 mg, 100%).

16732-57-3, The synthetic route of 16732-57-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; DAINIPPON SUMITOMO PHARMA CO LTD; IKUMA, YOHEI; IWATA, MASAKADO; NAKAI, YOSHIO; (62 pag.)JP2015/13821; (2015); 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.84807-09-0,4-(Piperazin-1-yl)-1H-indole,as a common compound, the synthetic route is as follows.,84807-09-0

EXAMPLE 12 1-[N-(2-nitrophenyl)-2-aminoethyl]-4-(4-indolyl)piperazine A mixture containing 0.49 g of N-(2-chloroethyl)-2-nitroaniline, prepared according to the procedure described by Ramage G. R. et al. in J. Chem. Soc. 4406-4409 (1952), 0.55 g of 1-(4-indolyl)piperazine (prepared according to WO 95/33743), 1 mL of triethylamine and 3 mL of DMF was heated at reflux while stirring under nitrogen for 2.5 h. After cooling at room temperature, the mixture was poured into H2O, extracted with CH2Cl2, and the organic phase dried on anhydrous Na2SO4 and evaporated to dryness. The residue was purified via flash chromatography (EtOAc-petrolium ether 3:7) giving 0.35 g (40percent) of the title compound. 1H-NMR (CDCl3, delta): 8.60-8.45 (br, 1H, aniline NH), 8.18 (dd, 1H, aniline H3), 8.20-8.10 (br, 1H, indole NH), 7.43 (td, 1H, aniline H5), 7.20-7.05 (m, 3H, indole H3,6,7), 6.85 (dd, 1H, aniline H4), 6.70-6.57 (m, 2H, aniline H6 and indole H5), 6.50 (t, 1H, indole H2), 3.45 (q, 2H, NHCH2CH2), 3.35-3.25 (m, 4H, piperazine protons), 3.85-2.70 (m, 6H, NHCH2 and piperazine protons).

As the paragraph descriping shows that 84807-09-0 is playing an increasingly important role.

Reference£º
Patent; Recordati S.A. Chemical and Pharmaceutical Company; US6399614; (2002); B1;,
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

98623-50-8, 2-(1H-Indol-5-yl)-N-methylethanesulfonamide is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,98623-50-8

A solution of 2-(1H-Indol-5-yl)-ethanesulfonic acidmethylamide (1) (3 g, 0.013 mol) in tetrahydrofuran (30 ml)was cooled to -70 to -80oC and then 2M solution of n-BuLi(0.2 g, 0.0031 mol) in THF (1.56 ml) was added drop wise atsame temperature and stirred for 30 minutes at -70 to -80oCfollowed by addition of methyl iodide (7.1 g, 0.05 mol). Theprogress of the reaction was monitored by TLC (mobilephase 8:2 ethyl acetate: hexane). After completion of thereaction, the reaction mass was quenched with isopropylalcohol and the solvent was distilled out under vacuum. Theresidue was taken in water and the compound was extractedwith ethyl acetate. The organic layer was dried over sodiumsulphate and distilled under vacuum at 50oC to give 2-(3-Methyl-1H-indol-5-yl)-ethanesulfonic acid methylamide (17)as white solid. Yield: 2.5 g (76%). Molecular formula:C12H16N2O2S; Calc. C, 57.14; H, 6.35; N, 11.11. Found: C,57.10; H, 6.30; N, 11.00. IR(KBr, numax, cm-1): 3415( -NH strof indole), 3989(-NH str of sulfonamide), 3050(aromatic -CH str.), 2953(aliphatic -CH str), 1517(-C=C str); 1HNMR(400 MHz, delta ppm, CDCl3): 2.67(d, 3H, J = 5.24 Hz,C12-H), 3.16-3.20(m, 2H, C10-H), 3.29-3.33(m, 2H, C11-H),3.75(s, 3H, C13-H), 4.20(q, 1H, NH of amide), 6.42(d, 1H, J= 3.4 Hz, ArC6-H), 7.04-7.07(m, 2H, ArC4-H & C2-H),7.23-7.27(m, 1H, ArC7-H ), 7.45-(s, 1H, NH protons of indole);13C NMR (400 MHz, delta ppm, CDCl3):29.38(C-12),30.08(C-10), 32.95 (C-13),52.72(C-11),100.67 (C-3), 109.72(C-6),120.29(C-7), 121.99(C-4), 128.56(C-2), 128.86(C-8),129.64(C-9), 135.79 (C-5); MS (m/z): 253.

The synthetic route of 98623-50-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Behera, Ajaya Kumar; Majumdar, Poulomi; Mohanta, Prajna Parimita; Mishra, Sushanta Kumar; Letters in Organic Chemistry; vol. 15; 4; (2018); p. 265 – 269;,
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.32387-18-1,1-(5-Bromo-1H-indol-3-yl)-2,2,2-trifluoroethanone,as a common compound, the synthetic route is as follows.

General procedure: One of compounds 3a-3f (20 mmol) was dissolved in DMF (10 mL). Trifluoroacetic anhydride (4.2 mL, 30 mmol) was added dropwise at 0C. After stirring for 3.5 h, water was added, the solid filtered off and treated with 20% NaOH (40 mL, 0.2 mol) at 55C overnight. Upon cooling down, the solution was extracted with Et2O. The aqueous phase was acidified with concentrated HCl and the residue was filtered off to give one of compounds 4a-4f., 32387-18-1

As the paragraph descriping shows that 32387-18-1 is playing an increasingly important role.

Reference£º
Letter; Zhang; Xu; Wang; Kang; Russian Journal of General Chemistry; vol. 87; 12; (2017); p. 3006 – 3016;,
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.16732-70-0,Ethyl 5-bromo-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.

A solution of the 3a (0.204 g, 0.5 mmol), ethyl 5-bromo-1Hindole-2-carboxylate (0.134 g, 0.5 mmol), Pd(dppf)2Cl2 (0.018 g,0.025 mmol) and Cs2CO3 (0.33 g, 0.56 mmol) in DMF (10 ml) underan atmosphere of N2 was stirred at 90 C for 4 h. DMF was removedunder reduced pressure and the residue was purified through acolumn chromatography on silica with chloroform/methanol (V:V20:1) as a white solid (0.12 g, 51.2% yield). mp 108-110 C. 1H NMR(400 MHz, DMSO) delta 12.00 (s, 1H, NH), 10.02 (s, 1H, NH), 8.27 (d,J 2.2 Hz, 1H, Ar-H), 7.87-7.80 (m, 4H, Ar-H), 7.55 (d, J 8.6 Hz, 1H,Ar-H), 7.49 (dd, J 8.6, 1.4 Hz, 1H, Ar-H), 7.43 (t, J 8.8 Hz, 2H, Ar-H), 7.22 (d, J 1.5 Hz, 1H, Ar-H), 4.36 (q, J 7.1 Hz, 2H, CH2), 3.66 (s,3H, CH3), 1.36 (t, J 7.1 Hz, 3H, CH3).13C NMR (100 MHz, DMSO)delta 164.8 (J 249.7 Hz), 161.7, 156.4, 141.6, 137.4, 137.1, 137.0, 132.3,131.1, 130.3 (d, J 9.6 Hz), 129.2, 128.7, 127.8, 124.2, 120.6, 120.2,116.7 (d, J 22.8 Hz), 113.8, 108.5, 61.0, 53.8, 14.8. HRMS: m/z470.1181 [MH]., 16732-70-0

As the paragraph descriping shows that 16732-70-0 is playing an increasingly important role.

Reference£º
Article; Fan, Yan-Hua; Li, Wei; Liu, Dan-Dan; Bai, Meng-Xuan; Song, Hong-Rui; Xu, Yong-Nan; Lee, SangKook; Zhou, Zhi-Peng; Wang, Jian; Ding, Huai-Wei; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 95 – 106;,
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

348-36-7, Ethyl 5-fluoro-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Ethyl 5-fluoro-1H-indole-2-carboxylate (2 g, 9.7 mmol) and 1H-pyrrole-2,5-dione (1.40 g, 14.4 mmol)were added to dry 1,2-dichloroethane (50 mL), and 46.5% BF3-Et2O (3.54 g, 11.6 mmol) was added toreaction mixture at 20 C. After the reaction mixture was stirred at 90 C, until the starting materialdisappeared in thin layer chromatography (TLC), the reaction mixture was distilled in vacuo, anddichloromethane (50 mL) was added to the mixture. The organic extract was washed twice withsaturated aqueous NaHCO3 and NaCl (20 mL) respectively, and the organic extract was dried overNa2SO4. After solvent was removed under vacuum, the product was purified as a white solid bysilica gel column chromatography, 1.62 g, yield 55%. 1H-NMR (400 MHz, DMSO-d6): = 12.00 (s, 1H,NH-indolyl), 11.31 (s, 1H, NH), 7.49-7.45 (m, 2H, H-indolyl), 7.18 (td, J = 9.2, 2.6 Hz, 1H, H-indolyl),4.82 (dd, J = 9.6, 6.6 Hz, 1H, CH), 4.33-4.27 (m, 2H, CH2), 3.08 (dd, J = 17.7, 9.6 Hz, 1H, CH?H?), 2.70(dd, J = 17.7, 6.6 Hz, 1H, CH?H?), 1.30 (t, J = 7.1 Hz, 3H, CH3). 13C-NMR (101 MHz, CD3OD): =182.17,180.15, 162.66, 160.66, 134.24, 129.01, 126.54, 119.11, 115.66, 114.82, 104.78, 62.19, 39.68, 39.37, 14.63.HRMS (ESI): m/z [M + H]+ calculated for C15H14O4N2F: 305.09321; found: 305.09290.

348-36-7, The synthetic route of 348-36-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wen, Hui; Liu, Yuke; Wang, Shufang; Wang, Ting; Zhang, Gang; Chen, Xiaoguang; Li, Yan; Cui, Huaqing; Lai, Fangfang; Sheng, Li; Molecules; vol. 24; 11; (2019);,
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

143612-79-7, 3-(4-Chlorobutyl)-1H-indole-5-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 3 (233 g, 1.0mol) and 6 (245 g, 1.0 mol) were dissolved in acetonitrile (3 L), and then, triethylamine (101 g, 1.0mol) and K2CO3 (138g,1.0mol) were added to the solution. The mixture was heated at reflux for 12 h. Subsequently, the reaction mixture was poured into cold water (3L). After filtration, the solid was dissolved in EtOAc, and then, HCl-EtOAc saturated solution was added to enable crystallization. Product 7 was obtained as a white solid. Yield 287 g (65%) with 99% HPLC purity after the mixture was filtered. m.p. 276.5-279.2C (Lit1 277-279C). 1H NMR (400MHz, DMSO-d6): delta 11.35 (s, 1H), 8.04 (d, J=18.3Hz, 2H), 7.74-6.88 (m, 8H), 3.69-3.15 (m, 8H), 2.74 (t, J= 7.2Hz, 2H), 2.37 (t, J =7.2Hz, 2H), 1.80-1.61 (m, 2H), 1.54 (d, J=6.8Hz, 2H). 13C NMR (100 MHz, DMSO-d6): delta 159.9, 148.8, 147.9, 138.6, 137.7, 127.8, 126.9, 124.7, 124.0, 123.3, 120.9, 117.8, 115.7, 112.4, 111.6, 109.5, 107.3, 100.0, 57.5, 52.8(2), 49.8(2), 27.7, 26.1, 24.1. HRMS (ESI): m/z [M+H]+ calculated for C26H27N5O2: 442.2238, found: 442.2240.

143612-79-7, As the paragraph descriping shows that 143612-79-7 is playing an increasingly important role.

Reference£º
Article; Hu, Fan; Su, Weike; Journal of Chemical Research; vol. 44; 3-4; (2020); p. 243 – 247;,
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

103858-53-3, Ethyl 6-bromoindole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

103858-53-3, Example 1 6-(4-TERT-BUTYLPHENYL)-1-(3-PHENOXYBENZYL)-3-PHENYLINDOLE-2-CARBOXYLIC acid (a) 6-(4-tert-Butylphenyl)indole-2-carboxylic acid ethyl ester A mixture of 6-BROMOINDOLE-2-CARBOXYLIC acid ethyl ester (400 mg, 1.5 mmol), 4-TERT-BUTYLPHENYLBORONIC acid (400 mg, 2.25 mmol), K3P04 (950 mg, 1.5 mmol), Pd (OAC) 2 (18 mg, 0.075 mmol), 2,2′-bis (di-tert- BUTYLPHOSPHINO)-L, l’-biphenyl (45 mg, 0.15 mmol), and toluene (9 ML) were stirred in an argon atmosphere for 30 min at room temperature, and at 100 C for 40 min using microwave irradiation. The mixture was cooled to room temperature and poured into NaHCO3 (aq. , sat. ). The mixture was extracted with EtOAc and the combined extracts were washed with water, brine and dried over NA2S04. The organic phase was then concentrated and the product purified by chromatography to give the sub-title compound (392 mg, 81%).

As the paragraph descriping shows that 103858-53-3 is playing an increasingly important role.

Reference£º
Patent; BIOLIPOX AB; MCNEENEY, Stephen, Phillip; WO2005/5415; (2005); 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