Day: August 19, 2020

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

l-(2-Chloroquinolin-6-yl)ethanone (lOOmg, 0.486 mmol) and 5-hydroxyindole (65 mg, 0.486 mmol), copper iodide (93 mg, 0.486 mmol) and cesium carbonate (475.3 mg, 1.46 mmol) were taken into DMF (8 ml) and heated in a microwave reactor at 15O0C for 50 min. The reaction was cooled to room temperature and water added to the reaction mass. The undissolved solids were filtered through celite and the filtrate was extracted with EtOAc twice. The organic extracts were washed with cold water and brine solution. The organic extracts were dried over sodium sulfate and concentrated under reduced pressure under vacuum. Purification of the residue by column chromatography (EtOAc:hexane 2:8) afforded 130 mg (88.4%) of l-[2-(lH-indol-5-yloxy)quinolin-6-yl]ethanone. LCMS [M+H] 303.5; 1H-NMR (400 MHz, CDCl3) delta 8.375-8.379 (d, IH, J=I .6 Hz), 8.27 (bs, IH), 8.17-8.19 (d, IH, J=8.8Hz), 8.13-8.16 (dd, IH, J=10.8 Hz, 6.8 Hz), 7.79-7.82 (d, IH, J=8.8 Hz), 7.49 -7.50 (d, IH, J=2Hz), 7.42-7.45 (d, IH, J=8.8 Hz), 7.27-7.28 (t, IH, 2.8 Hz), 7.12-7.14 (d, IH, J=8.8 Hz), 7.07-7.1 (dd, IH, J=I 1.2, 6.4 Hz), 6.57 (bs, IH), 2.69 (s, 3H) ppm. To a chilled solution of l-[2-(lH-indol-5-yloxy)quinolin-6-yl]ethanone (130 mg, 0.43 mmol) in DCM (10 ml) was added 4-(dimethylamino)pyridine (52.5 mg, 0.43 mmol). The mixture was stirred at O0C for 10 min after which di-t-butyl carbonate (0.158 ml, 0.86 mmol) was added. The reaction mixture was stirred for 30 min at ambient temperature. The reaction mixture was diluted with DCM and washed with water and brine before drying over sodium sulfate. The organic layer was evaporated under vacuum. Purification of the residue by column chromatography (EtOAc:hexane 2:8) afforded 140 mg (80.9%) yield of 5-(6-acetylquinolin-2-yloxy)indole-l-carboxylic acid tert-butyl ester. LCMS [M+H] 403.51; 1H-NMR (400 MHz, CDCl3) delta 8.382-8.386 (d, IH, J=I .6 Hz), 8.19-8.21 (d, 2H, J=8.8 Hz), 8.13-8.16 (dd, IH, J=10.8, 6.8 Hz), 7.77-7.79 (d, IH, J=9.2 Hz), 7.65-7.66 (d, IH, J=3.6 Hz), 7.430 -7.436 (d, IH, J=2.4 Hz), 7.18-7.20 (dd, IH, J=10.8, 6.8 Hz), 7.15-7.17 (d, IH, J=8.8 Hz), 6.57-6.58 (d, IH, J=3.6 Hz), 2.70 (s, 3H), 1.69 (s, 9H) ppm. 5-(6-Acetylquinolin-2-yloxy)indole-l-carboxylic acid t-butyl ester (140 mg, 0.348 mmol), ammonium acetate (322 mg, 4.175 mmol) and molecular sieves powder 4A (Ig) were taken into methanol (25ml) and stirred at room temperature for 20 min after which sodium cyanoborohydride (33 mg, 0.522 mmol) was added. The reaction mixture was refluxed overnight. The reaction mixture was cooled to room temperature and filtered through celite. The solvent was evaporated under vacuum to obtain crude which was dissolved in water and extracted with EtOAc. The EtOAc layer was washed with brine and dried over sodium sulfate. The organic layer was evaporated to obtain crude which was taken into the next step without further purification.

1953-54-4 5-Hydroxyindole 16054, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; FOREST LABORATORIES HOLDINGS LIMITED; SARMA, Pakala Kumara, Savithru; ACHARYA, Vinod, Parameshwaran; KASIBHATLA, Srinivas, Rao; TIWARI, Atul; REDDY, Vantaddu, Nagarjuna; BISCHOFF, Alexander; WO2010/127208; (2010); 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

1196-70-9, 1H-Indole-6-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 55. Synthesis of compound 2882-(2,6-dimethylpyridin-4-yloxy)acetohydrazide (100 mg, 0.51 mmol) and 1 H-indol-6- carbaldehyde (74 mg, 0.51 mmol) were dissolved in EtOH 2 mL, followed by stirring at 110 C for 12 hours. The reaction mixture was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and purified by columnchromatography (hexane:ethyl acetate = 2:1) to obtain Compound 288 (30 mg, 18 %).?H NMR (400 MHz, DMSO-d6): oe 11.43 (m, 1H), 11.28 (m, 1H), 8.35-8.07 (2s, 1H), 7.68 (d, J= 18.0 Hz, 1H), 7.57 (d, J- 8.4 Hz, 1H), 6.66 (d, J= 22.0 Hz, 2H), 6.47 (s, 1H), 5.20 (s, H),4.69 (s, 1H), 2.34 (m, 6H).

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

69047-36-5, 1-Methyl-1H-indole-7-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 6a (549 mg, 0.88 mmol) in anhydrous tetrahydrofuran (8 mL) at -78 C was treated dropwise with LiHMDS (1.3 mL, 1.30 mmol) and stirred at the same temperature for 0.3 h. A solution of indole-7-carboxyaldehyde (293 mg, 1.83 mmol) in anhydrous tetrahydrofuran (1 mL) was added dropwise, and the mixture was stirred at -78 C for 2 h. A saturated aqueous solution of NH4Cl (15 mL) was added at room temperature and the aqueous phase was extracted with ethyl ether (3 * 20 mL). The organic phase was dried (Na2SO4) and concentrated to give a mixture of diastereomers, which was used directly in the next step. Thus, the residue was dissolved in anhydrous dichloromethane (6 mL) and treated with triethylamine (0.54 mL, 3.52 mmol) and MsCl (0.14 mL, 1.76 mmol) at 0 C for 2 h. DBU (0.66 mL, 4.4 mmol) was added and the mixture was allowed to reach room temperature for 2 h. The reaction was quenched by the addition of NH4Cl (ss, 10 mL) and the aqueous phase was extracted with CH2Cl2 (3 * 20 mL). The organic phase was dried (Na2SO4) and concentrated. The residue was purified by silica gel flash column chromatography (gradient 0-20% EtOAc/hexanes) to give 528 mg (78% yield) of 7a as a colorless syrup.

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Reference£º
Article; Garcia, Lia C.; Donadio, Lucia Gandolfi; Mann, Ella; Kolusheva, Sofiya; Kedei, Noemi; Lewin, Nancy E.; Hill, Colin S.; Kelsey, Jessica S.; Yang, Jing; Esch, Timothy E.; Santos, Marina; Peach, Megan L.; Kelley, James A.; Blumberg, Peter M.; Jelinek, Raz; Marquez, Victor E.; Comin, Maria J.; Bioorganic and Medicinal Chemistry; vol. 22; 12; (2014); p. 3123 – 3140;,
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.

Example 10: Synthesis of 1-BENZYL-3-(4-TE7F-BUTYLPHENYL)-5-(LH-PYRROL-L-YL)- LH-INDOLE-2-CARBOXYLIC acid; [0122] Step 1:; A solution of N-BROMOSUCCINIMIDE (0.83 g, 4.7 mmol) in DMF (5 ML) was added dropwise to a stirred solution of ethyl 5-nitro-1H-indole-2-carboxylate (1.0 g, 4.27 mmol) in DMF (5 mL) at 0-5C. After the addition was completed, the reaction was warmed to room temperature and stirring was continued for an additional 1.5 h. The reaction mixture was poured over ice water and the resulting precipitate was collected and dried. The dried solid was re-dissolved in DMF (10 ML) and benzyl bromide (0.68 g, 4.0 mmol) and CS2CO3 (6.56 g, 20 mmol) were added successively. The reaction was stirred for overnight and then diluted with water. The product was extracted with ethyl acetate, dried over magnesium sulfate. Recrystalization from ethyl acetate and hexane gave 0.99 g (57%) of ethyl 1-BENZYL-3-BROMO-5- nitro-1 H-indole-2-carboxylate as an off-white solid : 1H NMR (DMSO-D6) No. 1. 28 (t, J = 7.0 Hz, 3 H), 4.35 (q, J = 7. 0 HZ, 2 H), 5.90 (s, 2 H), 7.00-7. 10 (m, 2 H), 7.20-7. 35 (m, 3 H), 7.95 (d, J= 9.3 Hz, 1 H), 8.25 (dd, J = 9.3, 2.0 Hz, 1 H), 8.48 (d, J = 2.0 Hz, 1 H); MS (ESI) m/z 403/405 (MH+).

16732-57-3 Ethyl 5-nitro-1H-indole-2-carboxylate 280312, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; WYETH; WO2005/30756; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.16732-64-2,4-Bromo-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

To a solution of compound 1 (0.36 g, 1.49 mmol, 1 eq) and compound 1A (366.33 mg, 1.49 mmol, 1 eq) in DMF (10 mL) was added HATU (851.82 mg, 2.24 mmol, 1.5 eq), DIEA (579.07 mg, 4.48 mmol, 780.41 uL, 3 eq) stirred at 15C for 16 hrs. LCMS showed the starting material was consumed and the desired MS was detected. The reaction was triturated with water (20 mL) and filtered. The filter cake was triturated with EtOAc (20 mL) and filtered. The filter cake was concentrated to give compound 2 (0.5 g, 1.07 mmol, 71.64% yield) as a yellow solid, which was confirmed. The residue was used directly next step without purification. LCMS: RT = 1.345 min, MS cal.: 467.32, [M+H] + = 468.7. 1H NMR (400MHz, DMSO-d6) d ppm 12.06 (s, 1H), 9.23 (s, 1H), 7.54 – 7.44 (m, 3H), 7.43 – 7.36 (m, 3H), 7.30 (d, J = 6.8 Hz, 1H), 7.17 – 7.10 (m, 1H), 6.72 (d, J = 2.0 Hz, 1H), 4.38 – 4.20 (m, 2H), 3.57 (br s, 2H), 2.14 – 1.96 (m, 2H), 1.89 (br d, J = 13.2 Hz, 2H).

As the paragraph descriping shows that 16732-64-2 is playing an increasingly important role.

Reference£º
Patent; KLEO PHARMACEUTICALS, INC.; BUNIN, Anna; IBEN, Lawrence G.; MANION, Douglas; SPIEGEL, David Adam; WELSCH, Matthew Ernest; (397 pag.)WO2019/136442; (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

52488-36-5, 4-Bromo-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-Bromo-lH-indole (1.95g, 10.0 mmol) and KOEta (0.84g, 15.0 mmol) were dissolved in acetone (15 mL). Tosyl chloride (2.86 g, 15 mmol) was added in one portion. The mixture was stirred at room temperature for 2h and concentrated to dryness. The residue was extracted with DCM and water, and washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified using silica gel chromatography with (PE:ethyl acetate = 5:1 as mobile phase) to give the title compound as a solid (2.1 g, 60%). LC/MS: m/e = 352 (M+H)+.

The synthetic route of 52488-36-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); 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.13544-43-9,6-(Trifluoromethyl)-1H-indole,as a common compound, the synthetic route is as follows.

In a round-bottomed flask, 1.0 g of 6-trifluorom- ethylindole (5.40 mmol; 1.00 eq) were dissolved in 10 mE of acetone (10.00 mE), 0.68 g of potassium hydroxide (12.15 mmol; 2.25 eq) were added to this dark orange solution and then the mixture was stirred at RT for 15 mm and 672 tE of iodomethan (10.80 mmol; 2.00 eq) were added. The reaction mixture was stirred at RT for 20 h. The reaction medium was then taken up with water and extracted with ethyl acetate. The organic phase was washed once with a saturated NaC1 solution, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromotography (l3iolage 50 g silica 30 microns adsorption on silica in dichloromethane) using a cyclohexane/ethyl acetate gradient of 99/1 to 90/10. The fractions containing the targeted product were combined and then evaporated under reduced pressure to give 835 mg of 1 -methyl-6-(trifluoromethyl)indole.10575] Yld: 78%. ?H NMR (300 MHz, DMSO-d5) oeppm 3.88 (s, 3H)6.56 (d, J=3.1 Hz, 1H) 7.30 (d, J=8.3 Hz, 1H) 7.57 (d, J=3.0Hz, 1H) 7.74 (d, J=8.3 Hz, 1H) 7.86 (s, 1H).

As the paragraph descriping shows that 13544-43-9 is playing an increasingly important role.

Reference£º
Patent; INVENTIVA; BOUBIA, Benaissa; MASSARDIER, Christine; GUILLIER, Fabrice; POUPARDIN, Olivia; TALLANDIER, Mireille; AMAUDRUT, Jerome; BONDOUX, Michel; FEENSTRA, Roelof Williem; VAN DONGEN, Maria Johana Petronella; (207 pag.)US2017/66717; (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

15317-58-5, 1H-Indole-3-carbohydrazide is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: 1H-Indole-3-carboxylate methylester 2 (1.0 mmol-equiv.) was refluxed with hydrazine hydrate(12.5 g, 0.25 M) in appropriate ethanol (30 mL) for 2 h. The progressof the reaction was monitored by TLC. After cooling the reactionmixture to room temperature, the mixtures were filtered to givewhite solid crude products without purification. Next, indolehydrazide(3, 1.0 mmol) in ethanol (30 mL) was added dropwiseinto the appropriate aldehyde (1.5 mmol-equiv.) and a few drops ofpropionic acid; the mixture was stirred and refluxed for 2.5 h. Aftercooling, the precipitates were filtered and washed several times bymethanol to yield the crystal substances 4aeu.

15317-58-5 1H-Indole-3-carbohydrazide 27199, aindole-building-block compound, is more and more widely used in various.

Reference£º
Article; Ju, Zhiran; Su, Mingzhi; Hong, Jongki; La Kim, Eun; Moon, Hyung Ryong; Chung, Hae Young; Kim, Suhkmann; Jung, Jee H.; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 86 – 98;,
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.23077-43-2,5-Fluoro-1H-indole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

5-fluoro-1 H-indole-3-carboxylic acid (450 mg),tert-butyl piperazine-1-carboxylate (466 mg),EDC (630 mg),HOBt (446 mg) and triethylamine (0.46 mL)Was dissolved in dichloromethane (25 mL)And the mixture was stirred at room temperature for 18 hours. Water was added to the reaction solution,It was extracted with dichloromethane and washed with saturated brine.The organic layer was dried over sodium sulfate,By distilling off the solvent under reduced pressure,tert-butyl 4- (5-fluoro-1 H-indole-3-carbonyl)Piperazine-1-carboxylate as a crude product.

The synthetic route of 23077-43-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NATIONAL CENTER FOR GERIATRICS AND GERONTOLOGY; YANAGISAWA, KATSUHIKO; KAWAI, AKIYOSHI; (139 pag.)JP2017/171619; (2017); 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

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