Month: August 2020

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.614-96-0,5-Methylindole,as a common compound, the synthetic route is as follows.

Example 3; 1. Synthesis of 3-cyanoindole derivatives with a terminal carboxylic acid; A basic synthetic method of a derivative with a terminal carboxylic acid is shown in the following scheme. [Show Image] An objective compound was prepared by (1) formylation of 3-position of the corresponding indole using phosphorus oxychloride in the presence of dimethylformamide (Vilsmeier method), (2) cyanation by dehydrating reaction with hydroxylamine in sodium formate and formic acid, (3) coupling with ethyl 4-fluorobenzoate in the presence of potassium fluoride on almina and 18-crown-5-ether in dimethylsulfoxide and then, (4) hydrolysis with lithium hydroxide in total 4 steps in that order. The results are shown in the following Table 1. In addition, XO-CH146 (R=H) was prepared from the third step using 3-cyanoindole purchased.; 1. Synthesis of XO-CH164 XO-CH155; Under an argon atmosphere, 5-methyl indole (1.04 g, 7.93 mmol) was dissolved in dimethylformamide (10 mL), and to the solution was added dropwise phosphorus oxychloride (2mL) under ice-cooling, and the resulting mixture was stirred for 1.5 hours at room temperature. To the reaction mixture was added dropwise an aqueous sodium hydroxide solution (5 g/15 mL) under ice-cooling, and the mixture was heated for reflux for an hour. The reaction mixture was adjusted to pH2 to 3 with concentrated hydrochloric acid under ice-cooling, and then, the solid was collected by filtration and dried at 60C under reduced pressure to give XO-CH155 as a pale pink solid (1.13 g, 90% yield).

The synthetic route of 614-96-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Kissei Pharmaceutical Co., Ltd.; EP1932833; (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

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.

General procedure: A solution of 2-(2-methyl-1H-indol-1-yl)ethanamine (4a) (65 mg, 0.373 mmol) and 4-(piperidin-1-yl)benzoic acid (5) (76 mg, 1 eq.), and dimethylaminopyridine (catalytic, ?5 mg) in dichloromethane (6 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide.hydrochloride (EDCI) (92 mg, 1.3 eq.) at room temperature. The resulting reaction mixture was stirred for 6h. At the conclusion of the reaction (TLC), water (15 mL) was added to quench the reaction. The product was extracted with ethyl acetate (20mL¡Á3). Organics were washed with dilute HCl (10 mL), saturated NaHCO3 solution (10 mL), water (10 mL) and brine solution (10 mL) and dried over Na2SO4 and concentrated. The resulting crude product was subjected to silica gel chromatography eluting with 0-40% ethyl acetate in hexane to furnish 7k (TG7-152) (100mg, 74% yield). 1H NMR (CDCl3): delta 7.52 (d, J=5.6Hz, 1H), 7.49 (d, J=8.8Hz, 2H), 7.30 (d, J=8Hz, 1H), 7.07 (m, 2H), 6.80 (d, J=8.2Hz, 2H), 6.23 (s, 1H), 5.98 (t, J=5.4Hz, 1H), 4.33 (t, J=6Hz, 2H), 3.76 (q, J=6Hz, 2H), 3.25 (t, J=4.8Hz, 4H), 2.37 (s, 3H), 1.6 (m, 6H). LCMS (ESI): >97% purity at lambda 254, MS; m/z, 362 [M+H]+. Anal. Calcd. for C23H27N3O: C, 76.42; H, 7.53; N, 11.62; found; C, 76.48; H, 7.55; N, 11.59.

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

Reference£º
Article; Ganesh, Thota; Jiang, Jianxiong; Dingledine, Ray; European Journal of Medicinal Chemistry; vol. 82; (2014); p. 521 – 535;,
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.

Step 3. Synthesis of (E)-N?-(( 1 H-indol-6-yl)methylene)-2-(4-(furan-3 -yl)-2,6- dimethylphenoxy)acetohydrazide: 2-(4-(furan-3 -yl)-2,6-dirnethylphenoxy)acetohydrazide(40 mg, 0.15 mmol) and 1 H-indol-6-carbaldehyde (22 mg, 0.15 mmol) were dissolved in EtOH2 mL, followed by stirring at 90 C for 3 hours. After the completion of the reaction, thereaction mixture was concentrated under reduced pressure, and purified by columnchromatography (hexane:ethyl acetate = 1:1) to obtain Compound 322 (19 mg, 32 %).?H NMR (400 MHz, DMSO-d6): 6 11.41-11.38 (m, 1H), 11.30-11.20 (m, 1H), 8.50- 8.04 (2s,1H), 8.08 (m, 1H), 7.88 (m, 1H), 7.61 (m, 1H), 7.48-7.37 (m, 2H), 7.38 (m, 1H), 7.27.(m, 3H),6.89 (m, 1H), 6.47 (m, 1H), 4.81 (s, 1H), 4.34 (s, 1H), 2.07 (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

51417-51-7, 7-Bromoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Anaerobic conditions,Cooled to 0 C with ice brine,Anhydrous DMF (2.5 g, 34 mmol) was taken in a 100 mL round bottom flask,P0C13 (1.4 g, 8.5 mmol) was added dropwise slowly,After about 10 minutes,0 C to continue the reaction for 30 minutes,Then 7-bromoindole (1.lg, 5.7mmol) was dissolved in 10 mL of DMF and slowly added dropwise to the reaction flask,After about 30 minutes at 0 C,Slowly rose to room temperature,The reaction was carried out for 5 hours,After TLC detection reaction was complete,The first reaction solution was added with saturated NaC03 solution,Adjusted to PH alkaline,While a large number of white solids appear,filter,The filter cake was washed 3 times with 100 mL of water,Dried to a yield of 1.2 g,Yield 94%.

51417-51-7 7-Bromoindole 2757020, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; Tianjin University of Science & Technology; YU, PENG; WANG, YIQIAN; JIA, HAIYONG; WEN, SHAOPENG; LYU, LEI; GUO, NA; HAN, KAILIN; CHU, JIE; WANG, TIANJIAO; (13 pag.)CN103864779; (2016); 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

15903-94-3, 6-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Ethylmagnesium bromide (44 mL, 134.5 mmol, 3.OM solution in Et20) was added dropwise at 0 ¡ãC to a solution of 6-(benzyloxy)-1H-indole (10 g, 44.8 mmol) over a period of 1 h in DCM (100 mL) under an atmosphere of argon. The resultant reaction mixture was warmed to room temperature and stirred for an additional 1 h. The above reaction mixture was cooled to 0 ¡ãC and treated with a solution of (9H-fluoren-9- yl)methyl (R)-(1-chloro-1-oxopropan-2-yl)carbamate (22 g, 67.2 mmol, crude) in DCM (100 mL) under an atmosphere of argon. After the addition was complete, the reaction was warmed to room temperature and stirred at rt for 12 h. The reaction mixture was cooled back to 0 ¡ãC and the excess of unreacted Grignard reagent was destroyed with aqueous HC1 (200 mL, 2N). The organic layer was separated and the aqueous layer was extracted with CH2C12 (2 x 200 mL). The combined organic layer was washed with water followed by brine, dried over sodium sulfate, filtered and concentrated to afford (R)-(9H-Fluoren-9-yl)methyl 1 -(6-(benzyloxy)- 1H-indol-3 -yl)-l -oxopropan-2-ylcarbamate (22.0 g, 42.6 mmol, crude) as abrown liquid. MS (ESI) m/z 517.35 [M+H] .

As the paragraph descriping shows that 15903-94-3 is playing an increasingly important role.

Reference£º
Patent; KALYRA PHARMACEUTICALS, INC.; HUANG, Peter, Qinhua; SLEE, Deborah, Helen; HEGDE, Sayee, Gajanan; HOPKINS, Chad, Daniel; BUNKER, Kevin, Duane; PINCHMAN, Joseph, Robert; SIT, Rakesh, Kumar; (137 pag.)WO2017/172957; (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.1215-59-4,5-(Benzyloxy)-1H-indole,as a common compound, the synthetic route is as follows.

4.1 To 6.7 g (30 mmol) 5-benzyloxyindole and 6.6 g (30 mmol) di-tert.-butyldicarbonate in 80 ml DMF were added 3.7 g (33 mmol) potassium tert. butylate at RT and the mixture was stirred at 60 C. for 4 h, cooled to RT and ether /0.5 M HC1 were added. The inorganic phase was extracted with ether, the combined organic phases were washed with water and dried over Na2SO4. Evaporation yielded crude 5-Benzyloxy-indole-1-carboxylic acid tert-butyl ester as colorless oil, MS: 323 (M).

The synthetic route of 1215-59-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ackermann, Jean; Aebi, Johannes; Dehmlow, Henrietta; Morand, Olivier; Panday, Narendra; Weller, Thomas; US2002/103247; (2002); 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.1074-87-9,(1H-Indol-7-yl)methanol,as a common compound, the synthetic route is as follows.

iv) 7-Indolecarboxaldehyde Solid pyridinium dichromate (1.77 g, 5.1 mmol) was added in portions over 3 hours to a stirred solution of 7-indolemethanol (0.5 g, 3.4 mmol) in dichloromethane (50 ml). The mixture was stirred for a further 2 hours then filtered through a pad of Celite filter aid. The filtrate was evaporated and the residue purified by chromatography on silica in ethyl acetate-hexane (1:3).

As the paragraph descriping shows that 1074-87-9 is playing an increasingly important role.

Reference£º
Patent; Lilly Industries Limited; US5281593; (1994); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.93957-49-4,3-(4-Fluorophenyl)-1-isopropyl-1H-indole,as a common compound, the synthetic route is as follows.

Examples 19 to 20 The reaction and post treatment were conducted in the same manner as in Example 14 except that acids shown in Table 3 were used instead of phosphorus oxychloride and the reaction time was 19 hours, to obtain methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylate (yellow solid). The results are shown in Table 3.

The synthetic route of 93957-49-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sumitomo Chemical Company, Limited; EP1666440; (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