Indole Building Blocks

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10075-52-2,5-Bromo-1-methyl-1H-indole,as a common compound, the synthetic route is as follows.

General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 ¡ãC for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

The synthetic route of 10075-52-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
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

4382-54-1, 5-Methoxyindole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(178-1) Under nitrogen atmosphere, to a solution of 5-methoxyindole-2-carboxylic acid (1.00 g) in Et2O (40 mL) was added LiAlH4 (280 mg) at 0 C., and the mixture was stirred under reflux for 3 hours. The mixture was treated with ethyl acetate, diluted with an aqueous hydrochloric acid solution, and extracted with ethyl acetate. The mixture was concentrated to give a crude alcohol compound (840 mg, 91%), which was dissolved in THF (10 mL), and stirred with MnO2 (4.20 g) at room temperature for 5 hours. The mixture was filtered on celite, and the filtrate was concentrated, and the residue was purified by silica gel column chromatography to give 5-methoxyindole-2-carbaldehyde (300 mg, 36%). 1H NMR (CDCl3, 400 MHz) delta 9.80 (s, 1H), 8.90 (brs, 1H), 7.34 (brd, 1H, J=8.9 Hz), 7.19 (dd, 1H, J=2.1 and 0.8 Hz), 7.11 (brs, 1H), 7.08 (dd, 1H, J=8.9 and 2.1 Hz), 3.86 (s, 3H).

As the paragraph descriping shows that 4382-54-1 is playing an increasingly important role.

Reference£º
Patent; Tokunaga, Teruhisa; Hume, William Ewan; Kitoh, Makoto; Nagata, Ryu; US2003/181496; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.54-16-0,2-(5-Hydroxy-1H-indol-3-yl)acetic acid,as a common compound, the synthetic route is as follows.

Structural Unit F-3; 3-(2-Hydroxy-ethyl)-1H-indole (F-3)LiAlH4 (1.99 g, 52.3 mmol) was placed in abs. THF (60 ml), under argon, and (5-hydroxy-1H-indol-3-yl)-acetic acid (5.00 g, 26.2 mmol) in abs. THF (100 ml) was added in the course of 30 min. The mixture was boiled for 3 h under reflux. For working up, THF (10 ml) and H2O (4 ml) were added to the mixture, while cooling with ice, and stirring was carried out for 30 min. The mixture was filtered over Celite and rinsed with dichloromethane (150 ml), and the filtrate was concentrated in vacuo.Yield: 2.17 g (47%)1H-NMR (DMSO-d6): 2.74 (2H, m); 3.60 (3H, m); 6.58 (1H, m); 6.78 (1H, s); 6.99 (1H, s); 7.08 (1H, d); 10.5 (1H, bs).

54-16-0 2-(5-Hydroxy-1H-indol-3-yl)acetic acid 1826, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; Gruenenthal GmbH; US2010/48554; (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.1006-94-6,5-Methoxyindole,as a common compound, the synthetic route is as follows.

General procedure: To the reaction mixture containing isatin (0.5mmol) in water (2mL), indole (0.5mmol), diethanolamine (20mol %) was slowly added at room temperature. After thecompletion of reaction as monitored by TLC, the reaction mixture was washed with brine solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the product was purified by flash chromatography on the silica gel column using a gradient of petroleum ether/ethyl acetate, as eluent to afford pure products 1-41.

As the paragraph descriping shows that 1006-94-6 is playing an increasingly important role.

Reference£º
Article; Sai Prathima, Parvathaneni; Rajesh, Pamanji; Venkateswara Rao, Janapala; Sai Kailash, Uppalapati; Sridhar, Balasubramanian; Mohan Rao, Mandapati; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 155 – 159;,
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

4769-97-5, 4-Nitroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A: Preparation of methyl (4-chlorophenyl)(4-nitro-lH-indol-l-yl)acetate (1)A solution of 4-nitroindole (6.89 g, 42.5 mmol) in DMF (20 mL) was added dropwise to a stirred suspension of sodium hydride (1.70 g of a 60percent wt/wt dispersion in mineral oil, 42.5 mmol) in DMF (100 mL) at 0 0C. After 10 min, a solution of He (11.2 g, 42.5 mmol) in DMF (20 mL) was added slowly dropwise, and the resulting mixture was stirred at 0 0C for 3 h. The reaction was quenched by addition of saturated aqueous ammonium chloride and extracted with ether. The combined organics were washed with water and brine, dried (MgS04), filtered and concentrated in vacuo. The resulting crude oil was purified by by flashchromatography on silica gel (gradient elution; 0percent-20percent EtOAc/hexanes as eluent) to afford the title compound 1. mlz (ES) 345 (MH)+; IP = C rating.

The synthetic route of 4769-97-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; CRESPO, Alejandro; LAN, Ping; MAL, Rudrajit; OGAWA, Anthony; SHEN, Hong; SINCLAIR, Peter J.; SUN, Zhongxiang; BUNTE, Ellen K. Vande; WU, Zhicai; LIU, Kun; DEVITA, Robert J.; SHEN, Dong-Ming; SHU, Min; TAN, John Qiang; QI, Changhe; WANG, Yuguang; BERESIS, Richard; WO2012/97744; (2012); 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.

1-(p-tolylsulfonyl}-6-(trifluoromethyl)indole; 6-Trifluoromethylindole (2.082 g; 10.908 mmol; 1.00 eq.) was dissolved intoluene (30.000 ml; 283.265 mmol; 25.97 eq.). Tetra-n-butylammoniumhydrogensulfat (555.541 mg; 1.636 mmol; 0.15 eq.), NaOH solution 32%(30.000 ml; 324.024 mmol; 29.71 eq.) and toluene-4-sulfonylchloride (3.183 g; 16.362 mmol; 1.50 eq.) were added at ooc. The solution was stirred for 14 h in a thawing ice bath. The reaction mixture was diluted with toluene and water,the organic layer was washed twice with a saturated solution of ammonia and1 x with water. The organic layer was dried over MgS04, filtered andconcentrated under reduced pressure. This gives 4 g (95%) of the titlecompound as a brown solid; HPLC MS (Method G): (M+H) 340; Rt 2.601 min.

The synthetic route of 13544-43-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK PATENT GMBH; BURGDORF, Lars; KUHN, Daniel; ROSS, Tatjana; DEUTSCH, Carl; WO2014/23385; (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

30464-93-8, 6-Methoxy-1H-indole-2-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To the stirred solution of 6-methoxy- lH-indole-2-carbaldehyde (1, 0.80 g, 4.57 mmol) in N, N-dimethylformamide (3 mL), cesium carbonate (4.4 g, 13.7 mmol) and l-bromo-2-methoxyethane (0.51 mL, 5.48 mmol) were added at room temperature. The reaction mixture was stirred at 60 C for 16 h. After completion of reaction, reaction mixture was diluted with water and extracted with ethyl acetate (200 mL x 2). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified by combiFlash using 12 g RediSep and 20% ethyl acetate in hexane as eluent to afford the 6-methoxy- l-(2-methoxyethyl)-lH-indole-2-carbaldehyde as off white semi solid. Yield: 0.60 g, 60%, MS (ESI): 235; m/z found 234.10 [M-l]”1.

As the paragraph descriping shows that 30464-93-8 is playing an increasingly important role.

Reference£º
Patent; JUBILANT BIOSYS LIMITED; HALLUR, Gurulingappa; DURAISWAMY, Athisayamani Jeyaraj; PURRA, Buchi Reddy; RAO, N.V.S.K.; RAJAGOPAL, Sridharan; (247 pag.)WO2019/58393; (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

51310-54-4, 2-(Trifluoromethyl)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 18 Preparation of 5-Nitro-2-(trifluoromethyl)indole STR35 A solution of 2-(trifluoromethyl)indole (0.2 g, 1.1 mmole) in acetic anhydride is treated with (0.131 g, 0.54 mmole of) Cu(NO3)2.3H2 O at 0 C., stirred for 2.5 hours at room temperature and diluted with water and ether. The phases are separated; the organic phase is washed sequentially with saturated NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo to give a yellow solid residue. The residue is chromatographed (silica gel/20% ethyl acetate in hexanes) to give the title product as a yellow solid, 0.073 g (29.4% yield), mp 190-193 C., identified by IR, 1 H-NMR, 19 FNMR and mass spectral analyses.

The synthetic route of 51310-54-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; American Cyanamid Company; US5502071; (1996); 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

14430-23-0, 5,6-Dimethoxyindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of appropriate intermediates 10-12 (1 mmol) in diethyl ether (5 mL) the oxalyl chloride (0.173 mL, 2 mmol) was added slowly at 0 C under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 2 h. A saturated aqueous NaHCO3 solution (5 mL) was added to quench the reaction and the mixture was extracted with EtOAc (3 x 10 mL). The combined extracts were dried with dry Na2SO4 and concentrated in vacuo. A mixture of crude compounds (20-22) (1 mmol) and N,N,N,N-tetramethyl- O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU) (379 mg, 1 mmol) in dimethylformamide (2 mL) was stirred for 30 min at room temperature. Successively, 4-benzylpiperidine (0.175 mL, 1 mmol) or 4-fluorobenzylpiperidine (193.3 mg, 1 mmol) and TEA (0.139 mL, 1 mmol) were added, the reaction mixture was stirred for 2 h at room temperature. Then the reaction mixture was quenched with H2O (10 mL) and extracted with EtOAc (3 x x10 mL). The combined extracts were dried with dry Na2SO4 and concentrated in vacuo. The crude compounds were purified by flash chromatography (FC) (DCM/MeOH 96:4) and recrystallized by treatment with Et2O to give the desired final products 29, 32-34.

The synthetic route of 14430-23-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Gitto, Rosaria; De Luca, Laura; Ferro, Stefania; Russo, Emilio; De Sarro, Giovambattista; Chisari, Mariangela; Ciranna, Lucia; Alvarez-Builla, Julio; Alajarin, Ramon; Buemi, Maria Rosa; Chimirri, Alba; Bioorganic and Medicinal Chemistry; vol. 22; 3; (2014); p. 1040 – 1048;,
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.10406-06-1,5-Bromo-1H-indole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

In a flask, the [2-amino-2-(5-bromo-lH-indol-3-yl)ethyl]carbamic acid tert-butyl ester (lb) (60 mg, 0.169 mmol) was dissolved in 5 mL of THF. To this solution, 5-bromo-lH-indole-3- carboxylic acid (2b) (41 mg, 0.169 mmol) and l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 33 mu?, 0.186 mmol) were added. The reacting mixture was stirred for 20 hours at room temperature. The homogeneous crude material was then diluted in a large amount of ethyl acetate (30 mL). The organic layer was washed twice with IN aqueous HCl and once with brine. The organic layer was dried over anhydrous MgS04 and concentrated. The crude material was purified by flash chromatography (EtOAc/pentane, 1/1 then 3/7) to afford the desired product 3f (67 mg, 0.116 mmol) as a white solid. Yield: 68%. Mp: 225 C (EtOAc/pentane). 1H NMR (300 MHz, MeOD): delta = 1.35 (s, 9H), 3.56-3.71 (m, 2H), 5.55-5.59 (m, 1H), 7.18 (dd, J = 1.8 and 8.6 Hz, 1H), 7.25-7.34 (m, 4H), 7.89-7.92 (m, 2H), 8.31 (br s, 1H) ppm. 13C NMR (75.5 MHz, MeOD): delta = 28.7 (C(CH3)3), 45.6 (CH2), 48.3 (CHN), 80.3 (C(CH3)3), 111.6, 113.3, 114.0, 114.3, 115.3, 122.5, 124.6, 124.7, 125.4, 126.3, 129.1, 129.4, 5 130.1, 136.7, 138.8, 159.0, 167.5 ppm. IR (ATR): 3429, 3376, 3296, 2985, 1729, 1647, 1625, 1525, 1457, 1361, 1254, 1164, 887, 790 cm”1. LRMS (ESI): m/z = 597, 599 and 601 [(M+Na)+]. HRMS (ESI) calcd for C24H24 403Br2 a: 597.0107, 599.0089 and 601.0073. Found: 597.0114, 599.0091 and 601.0071 [(M+Na)+].

10406-06-1 5-Bromo-1H-indole-3-carboxylic acid 7018243, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; UNIVERSITE JOSEPH FOURIER; DENIS, Jean-Noel; JOLIVALT, Claude, Marcelle; MAURIN, Max, Maurin, Louis; JEANTY, Matthieu; WO2013/14102; (2013); 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