Category: 13544-43-9

Walkington, Andrew et al. published their research in Synthetic Communications in 2003 | CAS: 13544-43-9

6-(Trifluoromethyl)-1H-indole (cas: 13544-43-9) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.SDS of cas: 13544-43-9

A simple two-step synthesis of indoles was written by Walkington, Andrew;Gray, Matthew;Hossner, Frank;Kitteringham, John;Voyle, Martyn. And the article was included in Synthetic Communications in 2003.SDS of cas: 13544-43-9 This article mentions the following:

A two-step synthesis of indoles that is suitable for use on a large scale is described. The general applicability of this methodol. was also briefly explored. In the experiment, the researchers used many compounds, for example, 6-(Trifluoromethyl)-1H-indole (cas: 13544-43-9SDS of cas: 13544-43-9).

6-(Trifluoromethyl)-1H-indole (cas: 13544-43-9) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.SDS of cas: 13544-43-9

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Some tips on 13544-43-9

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

13544-43-9, 6-(Trifluoromethyl)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

13544-43-9, To a solution of 6-trifluoromethyl indole (1.33 g, 7.18 mmol) in DMSO (7 mL) was added portionwise potassium hydroxide (0.75 mL, 13.37 mmol). The resulting solution was stirred at room temperature for 15 minutes. To this was added methyl-2-bromo propionate (3.6 mL, 32.29 mmol) in a single portion. The reaction mixture was stirred at room temperature for 16 hrs. The solution was cooled to 0 C. and quenched with water (20 mL). The mixture was extracted with CH2Cl2 (50 mL). This solution was washed with a saturated solution of ammonium chloride (2¡Á20 mL), brine (200 mL), dried over sodium sulfate, filtered, and concentrated. Purification via silica gel chromatography using 15-40% CH2Cl2 in hexanes gave the methyl ester as a clear oil (0.89 g, 3.23 mmol, 45% yield). LC/MS (10%/99% CH3CN (0.035% TFA)/H2O (0.05% TFA), m/z: M+1 obs=272.0; tR=3.56 min. 1H NMR (400 MHz, CDCl3) delta 7.73 (d, J=8.3 Hz, 1H), 7.62 (s, 1H), 7.45 (d, J=3.3 Hz, 1H), 7.39 (d, J=8.4 Hz, 1H), 6.67 (d, J=3.2 Hz, 1H), 5.26-5.20 (m, 1H), 3.76 (s, 3H), 1.88 (d, J=7.3 Hz, 3H).

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

Reference£º
Patent; Martinborough, Esther; Fanning, Lev T.D.; Sheth, Urvi; Wilson, Dean; Termin, Andreas; Neubert, Timothy; Zimmermann, Nicole; Knoll, Tara; Whitney, Tara; Kawatkar, Arati; Lehsten, Danielle; Stamos, Dean; Zhou, Jinglan; Arumugam, Vijayalaksmi; Gutierrez, Corey; US2008/27067; (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

Brief introduction of 13544-43-9

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

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

Simple exploration of 13544-43-9

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

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