61495-07-6

Usage

InChI:InChI=1/C14H12ClNO/c1-10-9-12(15)7-8-13(10)16-14(17)11-5-3-2-4-6-11/h2-9H,1H3,(H,16,17)

Upstream product

• 24251-12-5 tertiary amyl hypochlorite 
• 203209-58-9 N-benzylidene-4-chloro-2-methyl-aniline 
• 584-70-3 N-benzoyl-2-methylaniline 
• 98-88-4 benzoyl chloride 
• 95-69-2 4-chloro-2-methylbenzeneamine 
• 480438-47-9 (4-chloro-2-methylphenyl)magnesium bromide 

Downstream Products

• 1383796-89-1 6-chloro-2-phenyl-4H-benzo[d][1,3]oxazine 
• 1383797-26-9 6-chloro-4-methyl-2-phenylbenzo[d]oxazole 
• 147611-23-2 N-(4-chloro-2-formylphenyl)benzamide 
• 98083-43-3 1-Acetyl-5-chlorindazol 
• 1027899-02-0 (3S,4S)-4-(5-Chloro-2-phenyl-1H-indol-3-yl)-3-hydroxy-piperidine-1-carboxylic acid benzyl ester 
• 1027537-83-2 4-(5-chloro-2-phenyl-1H-indol-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 944910-17-2 N-(2-bromomethyl-4-chloro-phenyl)-benzamide 
• 698-26-0 5-chloro-1H-indazole 
• 170884-76-1 (5-chloro-2-phenylindol-3-yl)glyoxylyl chloride 

Relevant academic research and scientific papers

Room-temperature copper-catalyzed electrophilic amination of arylcadmium iodides with ketoximes

We started our study by preparation two ketoximes. Later, there were studies to reveal these ketoximes' effects in the electrophilic amination reaction with organocadmium reagents. Primarily, it was observed that arylcadmium iodides could not be reacted with ketoximes at room temperature in the absence of a catalyst. CuCN was a suitable catalyst for this electrophilic amination reaction of arylcadmium iodides and allowed the preparation of functionalized aniline derivatives in good yields under mild reaction conditions. We obtained the results indicated that the yield of primary arylamines was strongly dependent on the steric and electronic effects of organocadmium reagent and amination agent. In the case of both amination reagents, meta-substituted arylamines were obtained in higher yields than para-substituted arylamines. We observed that acetone O-(4-chlorophenylsulfonyl)oxime, 1, as an aminating agent, was more successful than acetone O-(2-Naphthylsulfonyl)oxime, 2, in the synthesis of functionalized arylamines by electrophilic amination of corresponding aryl cadmium iodides. In this method, there is no cadmium release to the environment.

High yielding electrophilic amination with lower order and?higher order organocuprates: Application of acetone O-(4-Chlorophenylsulfonyl)oxime in the construction of the C?N bond at room temperature

Electrophilic amination reaction was performed with lower order and?higher order organocuprates using acetone O-(4-Chlorophenylsulfonyl)oxime (1). It was proceeded smoothly at room temperature in the presence of organocuprates to provide the corresponding primary amines in good yields with 10 and 60 min, respectively. The primary amine yields of the electrophilic amination of bromomagnesium organocyanocuprates and dibromomagnesium diorganocyanocuprates were obtained 52–72% and 58–83%, respectively. We observed that higher order organocuprates were more successful than lower order organocuprates in the synthesis of functionalized arylamines by electrophilic amination.

Revisiting 1-chloro-1,2-benziodoxol-3-one: Efficient: ortho -chlorination of aryls under aqueous conditions

The application of 1-chloro-1,2-benziodoxol-3-one as a powerful chlorinating agent as well as oxidant for aniline derivatives is explored. The amide directing group assisted radical mediated ortho-selective chlorination proceeds in the absence of a radical initiator. Various electronically differentiated anilides and sulfonamides are tolerated under aqueous conditions.

Copper-catalyzed selective benzylic C-O cyclization of N-o-tolylbenzamides: Synthesis of 4 H-3,1-benzoxazines

A novel Selectfluor-mediated copper-catalyzed highly selective benzylic C-O cyclization for the synthesis 4H-3,1-benzoxazines is reported. The predominant selectivity for a benzylic C(sp3)-H over an aromatic C(sp 2)-H bond in N-o-tolylbenzamides is achieved.

Challenges in the development of mGluR5 positive allosteric modulators: The discovery of CPPHA

This Letter describes, for the first time, the synthesis and SAR, developed through an iterative analog library approach, that led to the discovery of the positive allosteric modulator (PAM) of the metabotropic glutamate receptor mGluR5 CPPHA. Binding to

Derivatives from isoselenocyanates: Synthesis of 2-phenyl-6H-[5,1,3] benzoselenadiazocine

The reaction of N-phenylbenzimidoyl isoselenocyanates 8 with primary and secondary amines in acetone at room temperature, followed by treatment with a base, led to 6H-[5,1,3]benzoselenadiazocine derivatives of type 10 (Scheme 3). An analogous cyclization was observed when 8a and 8b were reacted with the Na salt of diethyl malonate in EtOH at room temperature, which yielded the eight-membered selenaheterocycles 11 (Scheme 5). The molecular structures of some of the products, as well as that of a sulfur analogue, have been established by X-ray crystallography (Figs. 1-4). The isoselenocyanates 8 have been prepared from N-(2-methylphenyl)benzamides 5 in a three-step procedure via the corresponding imidoyl chlorides 6, side-chain chlorination to give 7, and treatment with KSeCN (Scheme 2).

3-(4-Fluoropiperidin-3-yl)-2-phenylindoles as high affinity, selective, and orally bioavailable h5-HT2A receptor antagonists

The development of very high affinity, selective, and bioavailable h5-HT2A receptor antagonists is described. By investigation of the optimal position for the basic nitrogen in a series of 2-phenyl-3-piperidylindoles, it was found that with the basic nitrogen at the 3-position of the piperidine it was not necessary to further substitute the piperidine in order to obtain good binding at h5-HT2A receptors. This meant the compounds no longer had high affinity at the IKr potassium channel, an issue with previous series of 2-aryl-3-(4-piperidyl)indoles. Improvements could be made to oral bioavailability in this series by reduction of the pKa of the basic nitrogen, by adding a fluorine atom to the piperidine ring, leading to 3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (17). Metabolic studies with this compound identified oxidation at the 6-position of the indole as a major route in vitro and in vivo in rats. Blocking this position with a fluorine atom led to 6-fluoro-3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (22), an antagonist with 0.06 nM affinity for h5-HT2A receptors, with bioavailability of 80% and half-life of 12 h in rats.

Lithiation of N-(2-Alkylphenyl)alkanamides and Related Compounds. A Modified Madelung Indole Synthesis

A modified Madelung synthesis for the conversion of N-(alkylphenyl)alkanamides and related compounds to indoles, benzindoles, and azindoles has been developed.This procedure consists of treating the amide with 2 or 3 equiv of n-butyllithium or lithium diisopropylamide in tetrahydrofuran at temperatures from -20 to +25 deg C.Several examples where products other than indoles were formed from the starting amide are also reported.

2-Substituted indoles and process for their preparation

Highly branched α-substituted indoles, e.g., 2-(1-methylcyclohexyl)-indole, are prepared by treating N-(α-branched carbonyl) toluidines with alkyl lithium. The reaction sequence may be illustrated as SPC1