92841-22-0

Usage

Uses

Used in Pharmaceutical Industry:
1-(6-Chloro-9H-carbazol-2-yl)ethanone (Carprofen Impurity) is used as an intermediate in the production of Carprofen, an NSAID for dogs with joint pain and arthritis. It plays a crucial role in the synthesis process, contributing to the development of effective treatments for canine patients suffering from inflammation and pain.

InChI:InChI=1/C14H10ClNO/c1-8(17)9-2-4-11-12-7-10(15)3-5-13(12)16-14(11)6-9/h2-7,16H,1H3

Upstream product

• 4360-63-8 2-bromomethyl-1,3-dioxolane 
• 5436-21-5 acetylacetaldehyde dimethyl acetal 
• 17422-32-1 5-chloro-1H-indole 
• 86-74-8 9H-carbazole 
• 23592-73-6 1-(2-acetylcarbazol-9-yl)ethanone 
• 99203-07-3 6-chloro-2,9-diacetylcarbazole 
• 23592-74-7 2-acetylcarbazole 

Downstream Products

• 53716-49-7 2-(6-chloro-carbazol-2-yl)-propionic acid 

Relevant academic research and scientific papers

Bismuth(III) Triflate Catalyzed Three-Component Reactions of Indoles, Ketones, and α-Bromoacetaldehyde Acetals Enable Indole-to-Carbazole Transformation

A three-component reaction of indoles, α-bromoacetaldehyde acetals, and ketones was developed by using bismuth(III) triflate as the catalyst to realize a straightforward approach for synthesizing carbazole derivatives. The reaction was established mechanistically through the autotandem catalysis of Bi(OTf)3 in the following two steps: (i) Friedel-Crafts-type alkylation of indole with α-bromoacetaldehyde acetal, which produced a tryptaldehyde-type intermediate and (ii) [4 + 2] annulation of this intermediate with the ketone component.

Syntheses of Carprofen, A Carbazole-Based Nonsteroidal Anti-Inflammatory Agent

Syntheses of carprofen (6) have been achieved by two approaches from carbazole (11).In one, 2,9-diacetylcarbazole (12) and 2-acetylcarbazole (13) were chlorinated with trichloroisocyanuric acid (15) to give the 6-chloro derivatives (16) and (17), respectively.Reduction of 16 with NaBH4, followed by acetylation, cyanide displacement, and hydrolysis afforded 6 in 73percent yield from 16.Alternatively, 17 was converted into its trimethylsilyloxy cyanohydrin derivative (27), which was reduced with SnCl2 and hydrolysed to give 6 in 75percent yield from 17.In the other approach, the ketone (18), derived by a Friedel-Crafts acylation of 9-acetylcarbazole with 2-chloropropanoyl chloride followed by chlorination with 15, was converted into the hydroxyketal (28) with methanolic NaOMe.Mesylation of 28, followed by a modified Favorskii rearrangement and hydrolysis gave 6 in 73percent yield from 18.