Category: indole-building-block

399-51-9, 6-Fluoro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of the Compound of Formula IIDetailed syntheses of the compound of Formula II from commercially available 6-fluoroindole are provided below. Scheme II uses diethoxymethane and dimethylamine to generate the ?iminium ion species?. An alternative procedure using formaldehyde in place of diethoxymethane is also provided below. Synthetic Procedure:Preparation of formaldehyde was carried out in reactor A. The synthesis of the compound of Formula II was carried out in reactor B. Precipitation of the final product was carried out in reactor C.Procedure:To reactor A were charged diethoxymethane (65 ml/54 g), water (50 ml) and formic acid (39 ml/47 g). The mixture was heated to about 80 C./reflux for about 2 hours and then cooled to about 20 C. To reactor B were charged 6-fluoroindole (50 g) and 80% acetic acid (66 ml/70 g, 2.5 eq. to 6-fluoroindole). The suspension was cooled to 2-5 C. 40% Dimethylamine (aq) (103 ml/92 g, 2.2 eq. to 6-fluoroindole) was added drop-wise to reactor B keeping the temperature below about 15 C. The reaction mixture was stirred for about 20 minutes and at the same time the temperature was adjusted to 2-4 C.The mixture from reactor A (DEM, water, formic acid, formaldehyde and ethanol at about 20 C.) was added drop-wise to reactor B while keeping the temperature at 2-8 C. The reaction mixture was stirred for additional 10 minutes at 2-8 C. The reaction mixture was slowly warmed to about 40 C. over a 1 hour period. The reaction mixture was stirred at about 40 C. for an additional 1 hour. The reaction mixture was cooled to about 20 C.To reactor C was charged 3M NaOH (800 ml, 1.24 eq. to the acetic acid+the formic acid) and the solution was cooled to about 10 C. The reaction mixture from reactor B was added drop-wise to the NaOH solution in reactor C while keeping the temperature at 10-15 C. (pH>14). The suspension was stirred for 40 minutes at 5-20 C. (pH>14). The product was collected by filtration and the filter-cake was washed twice with water (2×250 ml). The product was dried at about 60 C. under vacuum for 16 hours. Yield: 95%. Purity by HPLC (280 nm): 98 area %., 399-51-9

399-51-9 6-Fluoro-1H-indole 351278, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; H. LUNDBECK A/S; US2011/152539; (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.170147-29-2,tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of 1,1 -dimethylethyl 5-[(phenylmethyl)oxy]-lH-indole-l -carboxylate(1.76 g, 4.8 mmol) in tetrahydrofuran (10 mL) was added triisopropyl borate (2.2 mL, 9.5 mmol). The solution was stirred in an ice-water bath under a nitrogen atmosphere and lithium diisopropylamide (2 M in heptane/tetrahydrofuran/ethylbenzene) (4 mL, 8 mmol) was added, portionwise, over 20 min. The reaction mixture was swirled to facilitate mixing, then stirred with cooling for 45 m. Lithium diisopropylamide (2 M in heptane/tetrahydrofuran/ethylbenzene) (0.8 mL, 1.6 mmol) was added to the reaction mixture over a 5-min period. The cold reaction mixture was swirled to facilitate mixing, then stirred for 75 min. Hydrochloric acid (1 N) (50 mL) was added to the reaction mixture and the aqueous mixture was extracted with ethyl acetate. The organic extract was washed with water followed by saturated sodium chloride, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give 2.03 (100%) of {l-{[(l,l-dimethylethyl)oxy]carbonyl}-5-[(phenylmethyl)oxy]-l/f-indol- 2-yl}boronic acid as a tan solid. 1U NMR (400 MHz, DMSO-J6): delta 8.15 (s, 2H), 7.93 (d, J = 9 Hz, IH), 7.44 (d, 2H), 7.37 (m, 2H), 7.30 (m, IH), 7.15 (d, J = 2 Hz, IH), 6.94 (dd, J = 9, 2 Hz, IH), 6.51 (s, IH), 5.09 (s, 2H), 1.56 (s, 9H).

170147-29-2, As the paragraph descriping shows that 170147-29-2 is playing an increasingly important role.

Reference：
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/5998; (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.20289-27-4,7-(Benzyloxy)-1H-indole,as a common compound, the synthetic route is as follows.

Intermediate 32 Preparation of N-acetyltryotophan acetic anhydride (0.5 ML, 5.2 mmol) was added to a slurry of Intermediate 31 (0.575 g, 2.6 mmol) and DL-serine (0.270 g, 2.6 mmol) in anhydrous acetic acid (5 ML) at room temperature under a nitrogen blanket.The resulting orange solution was heated to reflux and stirred for 24 hours.The cooled mixture then was concentrated under reduced pressure to provide the intermediate N-acetyltryptophan as dark red oil, which was used immediately without purification

20289-27-4, 20289-27-4 7-(Benzyloxy)-1H-indole 260798, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Orme, Mark W.; Sawyer, Jason Scott; Daugan, Alain Claude-Marie; US2003/225092; (2003); 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

885518-25-2, 6-Fluoro-1H-indol-4-amine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,885518-25-2

To a solution of intermediate 12 (233.00 mg, 0.61 mmol), intermediate 34c (100.00 mg,0.67 mmol), Pd(OAc)2 (137.00 mg, 0.061 mmol) and Cs2CO3 (592.00 mg, 1.82 mmol) in1,4-dioxane (5 mL) was added BNAP (38.00 mg, 0.06 1 mmol) and the reaction mixturewas heated for 3 h at 95 C. The reaction mixture was then diluted with ethyl acetate and washed with water and brine. The organic layer was dried with sodium sulfate and concentrated in vacuo to give 397 mg of intermediate 35c (quant. yield, 76% purity based on LC/MS, dark black foam) which was used in the next step without any further purification.

The synthetic route of 885518-25-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (419 pag.)WO2018/2219; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2795-41-7,6-Fluoroindole-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

1.5 g 3-aldehyde-6-fluoroindole (ie intermediate I-1) was dissolved in isopropanol,Add 150 mg palladium on carbon and 3.2 g sodium borohydride,80 C reflux overnight.After TLC showed that the substrate disappeared,Filter to remove palladium carbon,After the filtrate is concentrated,Add water to quench excess sodium borohydride,Ethyl acetate extractionEach time 15ml,Extract 3 times.Organic layers merge,After drying over anhydrous sodium sulfate,Evaporated to drynessSilica gel column chromatography gave Intermediate I-2 (white solid, quantitative yield)., 2795-41-7

The synthetic route of 2795-41-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Hu Youhong; Geng Meiyu; Xing Weiqiang; Ding Jian; Ai Jing; (86 pag.)CN103664895; (2018); B;,
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.399-67-7,7-Fluoro-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

To a solution of 7-fluoroindole carboxylic acid (500 mg, 2.79 mmol, available from, for example, Matrix Scientific) in DMF (5 mL) was added potassium carbonate (771 mg, 11.2 mmol) followed by bromoethane (521 DL, 6.98 mmol). The reaction mixture was heated at 60 C for 2 h then further bromoethane (521 DL, 6.98 mmol) and potassium carbonate (771 mg, 11.2 mmol) were added. The reaction mixture was heated at 60 C for a further 2 h then concentrated under reduced pressure to give around 2 g of crude material as a beige solid.The material was suspended in a solution of THF (20 mL), water (20 mL) and MeOH (5 mL) then LiOH monohydrate (401 mg, 9.56 mmol) was added. The reaction mixture was stirred at rt for 16 h then concentrated under reduced pressure. The resulting crude product was treated with 2N HC1 (20 mL, aqueous), and the resulting beige solid filtered under reduced pressure then washed with water then further dried under reduced pressure to give the title compound as a beige solid (436 mg, 75%).LCMS (formic) MH+ = 208.0, Rt 1.03 mm

399-67-7, The synthetic route of 399-67-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AMANS, Dominique; ATKINSON, Stephen, John; BARKER, Michael, David; CAMPBELL, Matthew; DIALLO, Hawa; DOUAULT, Clement; GARTON, Neil, Stuart; LIDDLE, John; RENAUX, Jessica, Fanny; SHEPPARD, Robert, John; WALKER, Ann, Louise; WELLAWAY, Christopher, Roland; WILSON, David, Matthew; (284 pag.)WO2016/185279; (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

192189-07-4, tert-Butyl 3-iodo-1H-indole-1-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 10 (500mg, 1.Smmoi) in 5mL of dry dioxane was added 11(300mg, 2.9mmoi), CuT (30mg. 0.iSmmoi), Pd( Ph3)2C12 (70mg, 0.iSrnmoi) and TEA (400mg, 3.9mmoi). The mixture was degassed under vacuo and purged with N2 for several times. Then the mixture was stirred at 100C for 4h. TLC showed the obtaining of the product. The mixture was concentrated. The crude was washed with water (2OrnL) and extracted with EtOAc (8OmL).The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prepTLC to give product 12 (450 mg, yield: 94.3%).LCMS: m/z, 3 19.1 (M+H)., 192189-07-4

192189-07-4 tert-Butyl 3-iodo-1H-indole-1-carboxylate 10497531, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; LI, Yongguo; (44 pag.)WO2017/173604; (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.31241-19-7,5-Methoxy-2,3,3-trimethyl-3H-indole,as a common compound, the synthetic route is as follows.

General procedure: In parallel, substituted hydrazines 1 (4.0 g, 22.25 mmol) were reacted with 3-methylbutanone(3 mL, 28.04 mmol) in acetic acid and heated to a 100 C for 24 h. The solution was then neutralizedusing sodium bicarbonate and extracted using dichloromethane; affording substituted indolenineheterocycles 2 which was dried under reduced pressure. The heterocycles 2 were then reacted withan alkyl halide in acetonitrile at 100 C for 12-18 h. The quaternary ammonium salts 3 were precipitatedwith diethyl ether, and collected., 31241-19-7

31241-19-7 5-Methoxy-2,3,3-trimethyl-3H-indole 11095392, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Levitz, Andrew; Marmarchi, Fahad; Henary, Maged; Molecules; vol. 23; 2; (2018);,
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

59908-47-3, 5-Chloro-1-methyl-1H-indole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Version B: 780 mg of 1 d and 1747 mg of HATU were first dissolved in 10 ml DMSO. Next, 314 mg of 2-methoxyethylamine and 1080 mg of N,N-diisopropylethylamine were added. The mixture was stirred for 1 hr at RT. The reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue was purified chromatographically on the Biotage SP4. Gradient: ethyl acetate/methanol 0-10%. Yield: 740 mg of the title compound. Analogously to Example 1b, Version B, 43 mg of the title compound was obtained from 100 mg of 71a and 89 mg of 5-chloro-1-methyl-1H-indol-2-carboxylic acid in DMF. 1H-NMR (400 MHz, DMSO-d6): delta [ppm], 1.29 (2H), 1.38-1.72 (2H), 2.26-2.43 (1H), 2.54 (3H), 2.71-3.21 (2H), 3.73 (3H), 3.84-4.18 (3H), 4.38 (3H), 6.59 (1H), 7.15-7.28 (2H), 7.47 (1H), 7.55 (1H), 7.65 (1H), 8.57 (1H), 8.83 (1H)., 59908-47-3

59908-47-3 5-Chloro-1-methyl-1H-indole-2-carboxylic acid 931711, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; LlNDENTHAL, Bernhard; BRAeUER, Nico; SERNO, Peter; ROTGERI, Andrea; FUHRMANN, Ulrike; BUCHMANN, Bernd; MENGEL, Anne; ROeHN, Ulrike; TER LAAK, Antonius; (221 pag.)US2016/89364; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.851211-74-0,1H-Indole-6-carbohydrazide,as a common compound, the synthetic route is as follows.

851211-74-0, General procedure: Acetic acid (36%) (0.5 mL) was added to a mixture of compound 3 (1.5mmol) and benzene-1,4-dicarbaldehyde (0.5 mmol) in DMF (3 ml) atroom temperature. The solution was irradiated for 5-10 min at 450 W and compound 4 was formed. After the mixture was cooled to roomtemperature, water (30 mL) was added to the reaction. The solid which formed was filtered and recrystallised from DMF-C2H5OH-H2O, to give receptors 4a-h (yield 84-99).

As the paragraph descriping shows that 851211-74-0 is playing an increasingly important role.

Reference：
Article; Ye, Ying; Suo, Yourui; Yang, Fang; Yang, Yongjing; Han, Lijuan; Journal of Chemical Research; vol. 39; 5; (2015); p. 296 – 299;,
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