Tag: M.W:100-200

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55052-28-3,4-Chloro-7-azaindole,as a common compound, the synthetic route is as follows.

1H-4-chloro-pyrrolo[2,3-b]pyridine (0.765 g, 5 mmol, 1 eq.) was dissolved in DMF (7.5 mL, 1 .5 mL / mmol SM). NBS (0.935 g, 5.25 mmol) was added and the resulting solution was stirred at ambient temperature overnight, protected from light. Then, the solution was poured into ice-cold water (25 mL, 5 mL / mmol SM) and cooled into an ice bath. After ~10min the remaining suspension was filtered and the solid washed four times with 10 mL ice-cold water. Then the solid was collected and dried under high vacuum to give FH5295 as a yellow solid (1 .12 g, 4.8 mmol) in 96 % yield. 1H NMR (300 MHz, DMSO-d6) delta: 7.23 (d, J = 5.1 Hz, 1 H, H-5), 7.81 (d, J = 2.7 Hz, 1 H, H-2), 8.21 (d, J = 5.1 Hz, 1 H, H-6), 12.44 (br s, 1 H, N-H). 13C NMR (75 MHz, DMSO-d6) delta: 85.03 (C-3), 1 14.58 (C-3a), 1 17.13 (C-5), 127.71 (C-2), 134.17 (C-4), 144.18 (C-6), 147.98 (C-7a). HRMS (ESI): calculated for C7H5BrCIN2 ([M+H]+): 230.9319, found: 230.9332. Melting point: 210 C (decomposed)., 55052-28-3

55052-28-3 4-Chloro-7-azaindole 11389493, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; UNIVERSITEIT GENT; UNIVERSITEIT ANTWERPEN; HULPIA, Fabian; VAN CALENBERGH, Serge; CALJON, Guy; MAES, Louis; (146 pag.)WO2019/76633; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1196-70-9,1H-Indole-6-carbaldehyde,as a common compound, the synthetic route is as follows.

Example 37. Synthesis of compound 1942-(2-(trifluoromethyl)phenoxy)acetohydrazide (0.2 g, 0.85 mmol) and IH-indol-6-carbaldehyde(0.13 g, 0.85 mmol) were dissolved in ethanol, followed by stirring at 100 C for 16 hours.After the completion of the reaction, the reaction mixture was concentrated under reducedpressure. The concentrate was purified by column chromatography to obtain Compound 194(0.17 g, 55 %).?H NMR (400 MHz, DMSO-d6): oe 11.49-11.26 (m, 2H), 8.27-8.07 (m, 1H), 7.71-7.54 (m, 411), 7.44-7.42 (m, 2H), 7.20-7.06 (m, 2H), 6.45 (s, 1H), 5.3 1-4.80 (m, 2H).

1196-70-9, The synthetic route of 1196-70-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; INJE UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; CHOI, HoJin; LEE, JaeWon; LEE, ChangGon; HA, NiNa; SEO, Su Kil; LEE, SunMi; LEE, Song-Min; WO2014/35149; (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.31827-04-0,Methyl 3-hydroxy-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.

Acetobromo-alpha-D-galactose 1 (4.00 g, 9.72 mmol), indoxylic acid methyl ester 3(2.00 g, 10.46 mmol) and TBASH (3.55g, 10.46 mmol) were dissolved in biphasic solution of CH2Cl2 (60mL) and 1M K2CO3 (60 mL) that stirred at ambient temperature for 8 hours. The reaction mixture waspoured into a separatory funnel, phases were separated and the aqueous layer was extracted with CH2Cl2(2 x 50 mL). The combined organics were washed with H2O (200 mL) then dried over Na2SO4. Themixture was filtered through a silica gel pad and concentrated under reduced pressure. The residue waschromatographed via silica gel flash column (25-75% gradient EtOAc in hexanes) to afford the titlecompound 4 (3.64 g, 75% yield) as solid brown foam. The product was characterized as follows: Rf = 0.5,(1:1) EtOAc:Hexanes, visualized by KMnO4 stain (white spot); CHN calc. (%): C (55.28), H (5.22), N(2.69); found: (%): C (55.41), H (5.02), N (2.73), which corresponds to the literature.

31827-04-0, 31827-04-0 Methyl 3-hydroxy-1H-indole-2-carboxylate 3446522, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Article; Banasik, Brent; Mai, Tam; Samadpour, Mansour; Letters in Organic Chemistry; vol. 15; 10; (2018); p. 822 – 825;,
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

1477-49-2, 3-Indoleglyoxylic Acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1477-49-2

11.2 Hydrochloride of 3-[(R)-(1-aza-bicyclo[2.2.2]oct-3-yl)amino]-6-(1H-indol-3-yl)-4H-1,2,4-triazin-5-one A solution of 0.55 g of (1H-indol-3-yl)-oxo-acetic acid and 1.22 g of (R)-N-(1-aza-bicyclo[2.2.2]oct-3-yl)-hydrazinecarboximidamide hydroiodide, prepared in stage 11.1, in 3 cm3 of water is placed in a reactor. After sealing the tube, the mixture is submitted to discontinuous microwave irradiation for 20 min so that the temperature of the mixture is maintained at 140 C. Then cool the reaction mixture to a temperature close to 20 C., add methanol and evaporate to dryness under reduced pressure (2.7 kPa) to give a residue which is purified by flash chromatography on silica under argon pressure (50 kPa) [eluent: dichloromethane/methanol/ammonia 32% (75/22/3 by volume)]. After concentrating the fractions under reduced pressure (2.7 kPa), we get a residue which is washed successively with dichloromethane and ethyl ether, then dried under reduced pressure (2.7 kPa). The solid obtained is treated on a BOND ELUT VARIAN cartridge containing 2 g of SCX phase conditioned beforehand with methanol (eluent: methanol, then 2N ammoniacal methanol) and the appropriate fractions are evaporated under reduced pressure (2.7 kPa) to give a residue which is dissolved in ethanol and a 1N solution of hydrochloric acid in ethyl ether is added. The precipitate that forms is collected by filtration, washed with ethyl ether and dried under reduced pressure (2.7 kPa). We get 60 mg of hydrochloride of 3-[(R)-(1-aza-bicyclo[2.2.2]oct-3-yl)amino]-6-(1H-indol-3-yl)-4H-1,2,4-triazin-5-one in the form of an orange-colored solid. Mass spectrum (ES): m/z=337 (MH+). 1H-NMR spectrum (400 MHz)-delta in ppm-in DMSO-d6 referenced to 2.50 ppm: 1.79 (m, 1H); 1.92 (m, 2H); 2.10 (m, 1H); 2.22 (m, 1H); 3.11 (m, 1H); from 3.17 to 3.32 (m, 4H); from 3.60 to 3.90 (m partially masked, 1H); 4.22 (m, 1H); 7.11 (t, J=8.0 Hz, 1H); 7.18 (t, J=8.0 Hz, 1H); 7.46 (d, J=8.0 Hz, 1H); 7.90 (d broad, J=6.0 Hz, 1H); 8.30 (d, J=8.0 Hz, 1H); 8.60 (d, J=2.0 Hz, 1H); 9.92 (s broad, 1H); 11.5 (s broad, 1H); from 12.2 to 12.5 (m spread-out, 1H).

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

Reference£º
Patent; AVENTIS PHARMA S.A.; US2008/96891; (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

1953-54-4, 5-Hydroxyindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of [NAOH] (720 mg, 18 mmol) and acetone/water 1: 1 (72 ml), 4,6- dichloropyrimidine (2.4 g, [18 MMOL)] and 5-hydroxy-indole (2.68 g, 18 [MMOL)] are added. After stirring for 70 min at 65 [C,] the brownish solution is cooled to rt and diluted with AcOEt and water. The aqueous layer is separated off and extracted twice with AcOEt. The organic layers are washed with water, saturated Na2CO3 solution, water and brine, dried [(NA2SO4)] and concentrated. The crude product can be used without further purification: m. p.: 137-138 [C] ; MS: [[M+1] += 246.]

1953-54-4, As the paragraph descriping shows that 1953-54-4 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2003/99771; (2003); 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

1204-06-4, 3-Indoleacrylic Acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

NH2OTHP (0.38 g, 3.21 mmol) was added to a solution of trans-3-indoleacrylic acid (17) (0.50 g, 2.67 mmol), PyBOP (1.47 g, 2.83 mmol), triethylamine (0.74 ml, 6.41 mmol) in THF (25 mL). The mixture was stirred at room temperature for 2 h and then was concentrated under reduced pressure. The residue was dissolved in EtOAc and quenched with water, followed by extraction with EtOAc (20 mL*3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc:n-hexane=1.5:1:1% NH3(aq)) to afford 18. 1H NMR (500 MHz, CD3OD): delta 1.58-1.70 (m, 3H), 1.79-1.90 (m, 3H), 3.63-3.65 (m, 1H), 4.03-4.08 (m, 1H), 4.97-4.98 (m, 1H), 6.47 (d, J=14.9 Hz, 1H), 7.15-7.21 (m, 2H), 7.41 (d, J=7.8 Hz, 1H), 7.59 (s, 1H), 7.84-7.87 (m, 2H).

1204-06-4, The synthetic route of 1204-06-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Taipei Medical University; Ohio State University; National Taiwan University; US2011/245315; (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.883535-89-5,2-(2-Methyl-1H-indol-1-yl)ethanamine,as a common compound, the synthetic route is as follows.

883535-89-5, General procedure: Synthesis and structure activity relationship of 1 -indole cinnamic amide analog Indole-2 compounds were prepared as shown wherein step a is NaH, bromoacetonitrile, DMF, 75%; b is Lithium aluminum hydride (LAH), tetrahydrofuran (THF), 32-57%; c is Cinnamic acid derivative (14), l-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDCI), dimethylaminopyridine (DMAP), CH2C12, 75-80%). The compound 15a possess sites for structural modification, i) Trimethoxyphenyl group, ii) acryl amide moiety iii) ethylene linker, iv) a methyl group on the indole ring.

As the paragraph descriping shows that 883535-89-5 is playing an increasingly important role.

Reference£º
Patent; EMORY UNIVERSITY; GANESH, Thota; JIANG, Jianxiong; DINGLEDINE, Ray J.; WO2015/167825; (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.933-67-5,7-Methyl-1H-indole,as a common compound, the synthetic route is as follows.

General procedure: A 50 mL round-bottomed flask equipped with a magnetic stirringbar was charged with the appropriate indole 1 (0.5 mmol,1.0 equiv), 37% aq HCHO (0.5 mmol, 0.0406 g, 1.0 equiv), 25% aqNH3 (1.0 mmol, 0.0681 g, 2.0 equiv), FeCl3 (0.01 mmol, 0.0016 g,2 mol%), and DMF (2 mL). The flask was fitted with a reflux condenser,and the mixture was stirred at 130 C under open air.When the reaction was complete (TLC), the mixture was cooledto r.t., diluted with sat. aq NaCl (10 mL) and 0.5 M aq HCl (2 mL),and extracted with EtOAc (3 x 7 mL). The organic layers werecombined, washed with sat. aq NaHCO3 (10 mL) and sat. aq NaCl(10 mL), dried (Na2SO4), and concentrated under reduced pressure.The residue was purified by flash column chromatography(silica gel, hexane-EtOAc).

933-67-5, 933-67-5 7-Methyl-1H-indole 70275, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Article; Wang, Qing-Dong; Zhou, Bin; Yang, Jin-Ming; Fang, Dong; Ren, Jiangmeng; Zeng, Bu-Bing; Synlett; vol. 28; 19; (2017); p. 2670 – 2674;,
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

244-76-8, 9H-Pyrido[2,3-b]indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-necked 250ml flask, the compound (4) (0.6g, 1.23mmol), alpha-carboline (0.45g, 2.71mmol), NaOtBu (0.35g, 3.69mmol) were placed in toluene (100ml) was stirred under nitrogen, and the reaction temperature the temperature was raised to 80 C and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.02g, 0.04mmol), (tert-Bu) 3P (0.01g, 0.06mmol) and allowed to react at 80 C for 1 ~ 2days. Remove salts by filtration of the reaction solution It was. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain the compound (3-10, AnT-DaC3) 0.49g (yield: 60%)

244-76-8, The synthetic route of 244-76-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; WS Co., Ltd; Ko, Byung Soo; Kim, Kyu Sik; Oh, Yu Jin; (52 pag.)KR101528768; (2015); 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

14805-29-9, exo-Hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 2To the reaction mixture containing Compound (C) which was obtained in the above Example 1 were added (3aR,4S,7R,7aS)-hexahydro-4,7-methano-2H-isoindole-1,3-dione [Compound (D)] (22.6 g, 136.8 mmol), potassium carbonate (15.1 g, 109.3 mmol) and toluene (44 g).Then, the toluene (44 g) was distilled out from the mixture, water (0.82 g) was added thereto, and the resulting mixture was reacted under reflux for 8 hours.Then, the reaction mixture was cooled to room temperature, and water (400 g) was added to the mixture.The mixture was separated with a separating funnel, and the toluene layer was washed with 2.3percent (W/W) brine (350 g).Further, active carbon (1.8 g) was added to the toluene solution, and the mixture was stirred for 1 hour.The active carbon was removed by filtration to give a toluene solution containing (3aR,4S,7R,7aS)-2-{(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl) piperazin-1-ylmethyl]cyclohexylmethyl}hexahydro-4,7-methano-2H-isoindole-1,3-dione (2-[[(1R,2R)-2-[[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]methyl]cyclohexyl]-methyl]hexahydro-(3aS,4R,7S,7aR)-4,7-methano-1H-isoindole-1,3(2H)-dione) [Compound (E)] (341.4 g).The yield of Compound E was 94.3percent The yield of Compound (E) was calculated based on the analytical result that the content of the compound in the toluene solution was 12.4percent (w/w) (which was calculated by LC absolute calibration curve method).And, the production rate of by-product (R) was 0.013percent (which was calculated with the following formula (a))., 14805-29-9

Big data shows that 14805-29-9 is playing an increasingly important role.

Reference£º
Patent; Dainippon Sumitomo Pharma Co., Ltd.; US2011/263848; (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