Indole Building Blocks

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.913287-12-4,Ethyl 5-fluoro-7-nitro-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.

1.85 g (6.15 mmol) of ethyl 5-fluoro-7-nitro-1H-indole-2-carboxylate were initially charged in 20 ml of ethanol, admixed with 517 mg (9.22 mmol) of potassium hydroxide and stirred under reflux overnight. Subsequently, ethyl acetate was added, the mixture was extracted with 1 M sodium hydroxide solution and the pH of the aqueous phase was adjusted to pH 2 with hydrochloric acid.The mixture was extracted repeatedly with ethyl acetate, the organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate, filtered and concentrated. This gave 1.35 g (98% of theory) of the title compound.1H-NMR (400 MHz, DMSO-d6): delta=7.37 (d, 1H), 8.12 (dd, 1H), 8.16 (dd, 1H), 11.3 (s, 1H), 13.7 (s, 1H).

As the paragraph descriping shows that 913287-12-4 is playing an increasingly important role.

Reference£º
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2011/183928; (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

289483-87-0, 7-Amino-4-methyl-1H-indole-3-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Crystals of the title compound were synthesized using the same reaction conditions and recrystallization conditions as for the N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide described in WO00/50359. To a solution of 7-amino-3-cyano-4-methyl-1H-indole (10 g, 58.4 mmol) in tetrahydrofuran (200 ml) were added pyridine (20 ml) and 3-cyanobenzenesulfonyl chloride (12.5 g), followed by stirring at room temperature for 3.5 hours. After further adding 2N hydrochloric acid (100 ml), extraction was performed with ethyl acetate. The organic layer was washed with water (twice) and brine in that order, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate = 2:1-3:2). A mixed solvent of ethanol-hexane (1:2) was added thereto, and after sonication, the precipitate was collected by filtration and washed with a mixed solvent of ethanol-hexane (1:3). The mixture was dried overnight under reduced pressure to give the title compound (9.33 g, 27.7 mmol, 47% yield). 1H-NMR spectrum (DMSO-d6) delta (ppm): 2.58 (3H, s), 6.52 (1H, d, J=7.6Hz), 6.80 (1H, d, J=7.6Hz), 7.74 (1H, m), 7.92 (1H, d, J=8.0Hz), 8.12 (2H, m), 8.19 (1H, d, J=3.2Hz), 10.13 (1H, s), 12.03 (1H, s). A powder X-ray diffraction pattern for the obtained crystals is shown in Fig. 2, and the diffraction angle (2theta) peak and peak intensity are shown in Table 6. [Table 6] PEAK No. 2 theta HALF WIDTH d-VALUE INTENSITY RELATIVE INTENSITY 1 5.960 0.235 14.8167 3492 49 2 8.100 0.212 10.9063 2820 40 3 8.440 0.188 10.4677 1968 28 4 11.920. 0.259 7.4184 4067 57 5 14.120 0.282 6.2671 7103 100 6 15.120 0.259 5.8548 2142 30 7 16.400 0.165 5.4006 2330 33 8 17.660 0.141 5.0180 1905 27 9 17.960 0.212 4.9349 1998 28 10 19.240 0.306 4.6093 5707 80 11 21.380 0.235 4.1526 2443 34 12 21.940 0.282 4.0478 5502 77 13 23.020 0.212 3.8603 2602 37 14 23.580 0.165 3.7699 3172 45 15 23.900 0.400 3.7201 3958 56 16 24.540 0.282 3.6245 2812 40 17 25.840 0.165 3.4451 4302 61 18 26.520 0.212 3.3582 3045 43 19 27.540 0.376 3.2361 3265 46 20 28.380 0.118 3.1422 2655 37 21 28.520 0.188 3.1271 2435 34 It was attempted to produce identical crystals by the same process as Example 1B, but the powder X-ray diffraction pattern did not match. In other words, the crystals obtained in Example 1B were presumably not of a single crystal form but were a mixture of multiple crystal forms. Moreover, it is believed that a single crystal form cannot be produced by the process of Example 1B.

As the paragraph descriping shows that 289483-87-0 is playing an increasingly important role.

Reference£º
Patent; Eisai Co., Ltd.; EP1666463; (2006); 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