53924-05-3

Usage

Uses

Used in Chemical Synthesis:
7-Chloroindole is used as a chemical intermediate for the preparation of various compounds, such as 1-methyl-7-chloroindole and glycosylated 7-chloroindole-3-acetamide. Its unique chemical structure makes it a valuable building block in the synthesis of complex organic molecules, particularly in the pharmaceutical and chemical industries.
Used in Pharmaceutical Industry:
7-Chloroindole serves as a key component in the development of new drugs, particularly those targeting specific biological pathways. Its versatility in chemical synthesis allows for the creation of novel drug candidates with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 7-Chloroindole is utilized as a starting material for exploring new reaction pathways and understanding the reactivity of indole derivatives. This contributes to the advancement of knowledge in organic chemistry and the development of new synthetic methods.

InChI:InChI=1/C8H6ClN/c9-7-3-1-2-6-4-5-10-8(6)7/h1-5,10H

Synthetic route

methyl 7-chloro-indole-1-carboxylate → 7-chloro-1H-indole (53924-05-3)

Conditions	Yield
With potassium hydroxide In methanol for 1h; Reflux;	98%

2,3-dihydro-7-chloro-1H-indole (114144-22-8) → 7-chloro-1H-indole (53924-05-3)

Conditions	Yield
With salcomine; oxygen In methanol at 20℃; for 24h;	94%
With salcomine In methanol for 4h; Ambient temperature;	70%
With palladium on activated charcoal In toluene at 135℃; for 15h;	66%
With oxygen In methanol at 120℃; under 3800.26 Torr; for 12h;	79 %Chromat.

2-oxo-propionic acid (127-17-3) + (2-chlorophenyl)hydrazine (10449-07-7) → 7-chloro-1H-indole (53924-05-3)

Conditions	Yield
With phosphorus pentachloride; zinc(II) chloride for 0.0833333h; microwave irradiation;	80%

7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole (642494-37-9) → 7-chloro-1H-indole (53924-05-3)

Conditions	Yield
With copper dichloride In methanol; water at 80℃; for 4h;	75%
With copper dichloride In methanol; water at 80℃; for 4.5h; Inert atmosphere; Schlenk technique;	42%

7-chloroisatin (7477-63-6) → 7-chloro-1H-indole (53924-05-3)

Conditions	Yield
With potassium borohydride; boron trifluoride diethyl etherate In tetrahydrofuran at -10 - -5℃; Inert atmosphere;	71%

3-chloro-2-nitrotoluene (5367-26-0) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 7-chloro-1H-indole (53924-05-3)

Conditions	Yield
Stage #1: 3-chloro-2-nitrotoluene; N,N-dimethyl-formamide dimethyl acetal With pyrrolidine In 1,4-dioxane at 102℃; for 9h; Leimgruber-Batcho Indole Synthesis; Reflux; Inert atmosphere; Stage #2: With hydrazine hydrate In 1,4-dioxane at 45℃; for 1h; Leimgruber-Batcho Indole Synthesis;	70%

vinyl magnesium bromide (1826-67-1) + 2-Chloronitrobenzene (88-73-3) → 2-oxoindole (59-48-3) + 7-chloro-1H-indole (53924-05-3)

Conditions	Yield
In tetrahydrofuran at -40℃;	A 33% B 63%

vinyl magnesium bromide (1826-67-1) + 2-Chloronitrobenzene (88-73-3) → 7-chloro-1H-indole (53924-05-3)

Conditions	Yield
Stage #1: vinyl magnesium bromide; 2-Chloronitrobenzene In tetrahydrofuran at -40 - 0℃; for 2.5h; Bartoli Indole Synthesis; Stage #2: With ammonium chloride In tetrahydrofuran at 0℃; for 0.5h; Bartoli Indole Synthesis;	60%
In tetrahydrofuran at -40℃; for 1h;	56%

vinyl magnesium bromide (1826-67-1) + 2-Chloronitrobenzene (88-73-3) → 7-chloro-1H-indole (53924-05-3) + 3,3’-ethane-1,1-diylbis(7-chloro-1H-indole) (1445721-16-3)

Conditions	Yield
Stage #1: vinyl magnesium bromide; 2-Chloronitrobenzene In tetrahydrofuran at -40 - 0℃; for 2.5h; Stage #2: With potassium hydrogensulfate In tetrahydrofuran; water at 0℃; for 0.5h; Reagent/catalyst;	A 8% B 34%

Upstream product

• 28899-75-4 7-Chloro-1H-indole-2-carboxylic acid 
• 105896-40-0 N-(2-chlorophenyl)ethenesulfinamide 
• 1826-67-1 vinyl magnesium bromide 
• 88-73-3 2-Chloronitrobenzene 
• 102-71-6 triethanolamine 
• 95-51-2 o-chloroaniline 
• 18159-32-5 Δ¹⁽⁸⁾-hexahydroindole 
• 104682-95-3 1-acetyl-2,3-dihydro-7-iodoindole 
• 43142-70-7 ethyl (E)-2-(2-(2-chlorophenyl)hydrazono)propanoate 
• 127-17-3 2-oxo-propionic acid 
• 10449-07-7 (2-chlorophenyl)hydrazine 
• 5367-26-0 3-chloro-2-nitrotoluene 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 7477-63-6 7-chloroisatin 

Downstream Products

• 145852-78-4 1-Benzyloxymethyl-3-bromo-4-(7-chloro-1H-indol-3-yl)-pyrrole-2,5-dione 
• 102192-77-8 1-Benzyloxymethyl-3,4-bis-(7-chloro-1H-indol-3-yl)-pyrrole-2,5-dione 
• 145852-80-8 3,4-dihydro-3-<7-chloro-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-indol-3-yl>-4-(7-chloro-1H-indol-3-yl)-1-(benzyloxymethyl)-1H-pyrrole-2,5-dione 
• 78225-46-4 3-bromo-7-chloroindole 
• 159503-76-1 7-chloro-N,N-dimethyl-1H-indole-3-methanamine 
• 3804-16-8 2-(7-chloro-1H-indol-3-yl)ethanamine 
• 863289-28-5 2-(7-chloro-1H-indol-3-yl)-2-oxoacetyl chloride 
• 480435-91-4 3-(7-chloro-1H-indol-3-yl)-2,5-dichloro[1,4]benzoquinone 
• 77290-47-2 N-Acetyl-7-chlor-DL-tryptophan 
• 896137-69-2 7-chloro-1-(phenylsulfonyl)-1H-indole 
• 1004558-41-1 7-chloroindole-1-carboxylic acid tert-butyl ester 
• 852391-20-9 (S)-5-(7'-Chloro-1H-indol-3ylmethyl)-3-methyl-imidazolidine-2,4-dione 
• 852391-20-9 (R)-5-((7-chloro-1H-indol-3-yl)methyl)-3-methylimidazolidine-2,4-dione 
• 870481-87-1 2-tert-butoxycarbonylamino-3-(7-chloro-1H-indol-3-yl)-propionic acid 

Relevant academic research and scientific papers

Reversible aerobic oxidative dehydrogenation/hydrogenation of N-heterocycles over AlN supported redox cobalt catalysts

N-heterocycles with quinoline and tetrahydroquinoline structures are highly important in pharmaceutical and chemical industries, and their highly efficient mutual transformations are vital but still challenging. In the present work, AlN supported redox cobalt catalysts (Co3O4/AlN and Co/AlN) were prepared, which could achieve the reversible aerobic oxidative dehydrogenation/hydrogenation of N-heterocycles with good performances. The catalytic performances were stem from the strong interaction between Co species with AlN support, which were confirmed by the characterizations of Raman, XPS, UV–vis DRS, and H2-TPR etc. Both of the catalysts showed good stabilities and reusabilities for the titled reactions. Besides, the gram-scale experiments achieved with good yields to corresponding products, revealing the present protocol possesses great potential applications in industry. The strategy of using redox Co-based catalyst not only provides a potential catalyst for the reversible hydrogenation/oxidative dehydrogenation reactions but also replenishes methods for constructing of other redox catalyst, especially with AlN as a carrier.

Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3

Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C?H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C?H borylation enabling selective formation of C5-BPin-indoles.

A indole compound and its preparation method and application (by machine translation)

The invention discloses a indole compound and its preparation method and application. The indole compounds of the structural formula such as formula (I) is shown. The indoles, rice galenical demonstrate the excellent inhibitory activity, the effect of most of the compound is obviously better than the positive control drug validamycin; especially compound I - 43, I - 44, I - 54, I - 73, II - 7 and II - 17, its galenical very good living body protection and treating effect, effect is better than the positive control; more specifically, compound I - 43 of the rice sheath blight bacteriostatic activity than validamycin activity is improved by nearly 300 times. The indole compounds in the prevention and/or treatment of rice sheath blight has great application prospects. In addition the compound of the invention is simple in construction, the preparation method is simple, and is suitable for large-scale industrial production. (I). (by machine translation)

Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis

A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).

Synthesis of 7-halo indoles (by machine translation)

The present invention relates to synthesis of 7? Halo indole method, comprising the steps of:O-halogenated aniline, chloral hydrate and hydroxylamine hydrochloride by the Sandmeyer reaction to synthesize 7? halogenating isatin ; 7? halogenating isatin dissolved with an organic solvent, in the reducing agent by reduction reaction under the conditions of 7? Halo indole, the reducing agent is an alkali metal borohydride system, four system adopts, lithium hydride system or triethyl silane system. The beneficial effect of the invention is:in order to O-halogenated aniline and the chloral hydrate is, hydroxylamine hydrochloride as raw materials, by the Sandmeyer shall synthesis method for preparing compositions b isonitroso 7? halogenating isatin, and then by further reduction and system reduction to prepare 7? Halo indole; by the 7? Preparation halogenating isatin 7? Halo indole method, the raw material is easy to obtain, low price, higher process yield, the product purity is good, simple operation, and the like, is suitable for batch preparation 7? Halo indole. (by machine translation)

Catalytic synthesis method of indole compounds

The invention discloses a catalytic synthesis method of indole compounds.The method includes the following steps of firstly, conducting stirring reaction on ortho-nitrostyrolene or derivatives of ortho-nitrostyrolene, bis(pinacolato)diboron, alkali and low-grade saturated monohydric alcohol under the atmosphere of nitrogen; secondly, cooling the reaction product in the first step to the room temperature, adding ethyl acetate to be sufficiently mixed, and washing with ethyl acetate after filtering; thirdly, spin-drying low-grade saturated monohydric alcohol in an organic phase of the material obtained in the second step, passing through a silica gel column, and drip washing the silica gel column with eluent composed of petroleum ether and ethyl acetate to obtain pure products, namely, the indole compounds.By means of the method, under the neutral conditions, bis(pinacolato)diboron low in price serves as the raw material, friendly low-grade saturated monohydric alcohol serves as the solvent, the indole compounds are obtained through simple operation, the raw materials are low in price and easy to obtain, efficiency and safety are high, and wide expandability and good industrial application prospects are achieved.

Total Synthesis of (-)-Nodulisporic Acid D

A convergent total synthesis of the architecturally complex indole diterpenoid (-)-nodulisporic acid D has been achieved. Key synthetic transformations include vicinal difunctionalization of an advanced α,β-unsaturated aldehyde to form the E,F-trans-fused 5,6-ring system of the eastern hemisphere and a cascade cross-coupling/indolization protocol leading to the CDE multisubstituted indole core.

N-(2-ARYLETHYL) BENZYLAMINES AS ANTAGONISTS OF THE 5-HT6 RECEPTOR

The present invention relates to the use compounds of formula I which are antagonists of the 5-HT 6 receptor, for treating a cognitive disorder selected from the group consisting of age-related cognitive decline, mild cognitive impairment and dementia

One-pot tandem synthesis of 2,3-unsubstituted indoles, an improved Leimgruber-Batchoindole synthesis

A concise, fast and efficient one-pot methodology has been developed for preparing 2,3-unsubstituted indoles from 2-nitrotoluenes and dimethylformamide dimethyl acetal. Compared with the classical Leimgruber-Batcho reaction, such a one-pot process simplified the operation procedures, generated less by-products and chemical residues, and resulted in higher overall yields in a shorter reaction time.

One-pot construction of 3,3′-bisindolylmethanes through Bartoli indole synthesis

A one-pot approach to 3,3′-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3′-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH 4Cl.