1196-39-0

Usage

Chemical Description

4-methylquinoline is a heteroaromatic base, and phenyl vinyl sulfone is an activated olefin.

Uses

Used in Organic Synthesis:
4-Methylquinoline is used as a synthetic intermediate for the production of various organic compounds. Its unique structure and chemical properties make it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-methylquinoline is used as a key component in the development of new drugs. Its versatile chemical properties allow for the creation of a wide range of drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
4-Methylquinoline is also utilized in the agrochemical industry for the synthesis of various pesticides and insecticides. Its unique structure and reactivity enable the development of novel compounds with improved efficacy and selectivity.
Used in Specialty Chemicals:
In the specialty chemicals sector, 4-methylquinoline is employed as a raw material for the production of dyes, pigments, and other colorants. Its ability to form stable complexes with various metal ions makes it an attractive candidate for the development of new colorant technologies.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 5312, 1980 DOI: 10.1021/jo01314a019Tetrahedron, 38, p. 3347, 1982 DOI: 10.1016/0040-4020(82)80117-8

InChI:InChI=1/C10H9N/c1-8-6-11-7-9-4-2-3-5-10(8)9/h2-7H,1H3

Upstream product

• 86457-01-4 4-methyl-3,4-dihydro-isoquinoline 
• 50-00-0 formaldehyd 
• 114273-47-1 C₁₅H₂₃BN^(1-)*Na⁽¹⁺⁾ 
• 767-59-9 1-Methylinden 
• 93424-04-5 N-benzyl N-(propenyl-1) orthophenyl benzamide 
• 1532-97-4 4-bromoisoquinoline 
• 676-58-4 methylmagnesium chloride 
• 13061-96-6 dihydroxy-methyl-borane 
• 75-16-1 methylmagnesium bromide 
• 215031-61-1 tri-n-butyl(4-isoquinolyl)stannane 
• 74-88-4 methyl iodide 
• 685103-98-4 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline 
• 85070-52-6 rac-N-(2-phenylpropyl)formamide 
• 582-22-9 2-phenylpropylamine 

Downstream Products

• 24188-78-1 1-chloro-4-methylisoquinoline 
• 14428-50-3 2-(4-methoxyphenyl)-4-methyl-quinoline 
• 111661-47-3 4-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 651310-24-6 5-bromo-4-methylisoquinoline 
• 110841-71-9 4-methyl-1,2,3,4-tetrahydro-isoquinoline 

Relevant academic research and scientific papers

-Annulation of gem-Difluoroalkenes and Pyridinium Ylides: Access to Functionalized 2-Fluoroindolizines

A [3 + 2]-annulation of gem-difluoroalkenes and pyridinium ylides was developed employing ambient air as the sole oxidant in an open-vessel manner, affording a series of multifunctionalized 2-fluoroindolizines in moderate to good yields. In this reaction, gem-difluoroalkene acts as a C2 synthon and entirely avoids the competitive addition-elimination process, which provides facile access to 2-fluoroindolizines.

ISOQUINOLINESULFONYL DERIVATIVE AS RHO KINASE INHIBITOR

The present invention discloses a class of isoquinolinesulfonyl derivatives as RHO kinase inhibitors, and pharmaceutical compositions thereof, and relates to pharmaceutically acceptable uses thereof. Specifically, the present invention relates to a compound as represented by formula (I), or a pharmaceutically acceptable salt thereof.

Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by Chiral Diborons

We herein describe a chiral diboron-templated highly diastereoselective and enantioselective reductive coupling of isoquinolines that provided expedited access to a series of chiral substituted bisisoquinolines in good yields and excellent ee's under mild conditions. The method enjoys a broad substrate scope and good functional group compatibility. Mechanistic investigation suggests the reaction proceeds through a concerted [3,3]-sigmatropic rearrangement.

Hepatitis C virus inhibitors

Hepatitis C virus inhibitors having the general formula (I) are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

Hepatitis C Virus Inhibitors

Hepatitis C virus inhibitors having the general formula (I) are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

METHOD FOR RAPIDLY METHYLATING HETEROAROMATIC ARENE AND METHOD FOR PRODUCING TRACER FOR USE IN PET

Provided is a method whereby a heteroaromatic ring aryl can be very rapidly methylated at a high yield. In an N-alkyl-2-pyrrolidinone, a heteroaromatic ring aryltrialkylstannan is cross-coupled with methyl iodide in the presence of a palladium complex, a phosphine ligand, a cuprous halide, a carbonic acid salt and/or an alkali metal fluoride to thereby rapidly methylate the heteroaromatic ring aryl. (Formula shows a case wherein the heteroaromatic ring aryl is a pyridyl group.)

Pd0-mediated rapid coupling between methyl iodide and heteroarylstannanes: an efficient and general method for the incorporation of a positron-emitting11C radionuclide into heteroaromatic frameworks

The Pd0-mediated rapid trapping of methyl iodide with an excess amount of a heteroaryl-substituted tributylstannane has been investigated with the aim of incorporating a shortlived 11C-labelled methyl group into the heteroaromatic carbon frameworks of important organic compounds, such as drugs with various heteroaromatic structures, in order to execute a positron emission tomography (PET) study of vital systems. The reaction was first performed by using our previously developed CH3I/stannane/[Pd 2(dba)3]/ P(o-CH3C6H 4)3/CuCl/K2CO3 (1:40:0.5:2:2:2) system in DMF at 60°C for 5 min (conditions A), however, the reaction gave low yields for various heteroaromatic compounds. Increasing the amount of phosphine ligand (condi tions B) led to a significant improvement in the yield, but the conditions were still not suitable for a range of basic heteroaromatic structures. Use of the CuBr/CsF system (conditions C) also provided a result similar to that obtained under conditions B with an increased amount of the phosphine. Thus, pyridine and related heteroaromatic compounds remained less reactive substrates. The problem was overcome by replacing the DMF solvent with N-methyl-2-pyrolidinone (NMP). The reaction in NMP at 60-100°C for 5 min using a CH3I/stannane/[Pd2-(dba)3]/P(o-CH 3C6H4)3/CuBr/CsF (1:40:0.5:16:2:5) combination (conditions D) gave the methylated products in yields of more than 80% (based on the reaction of CH3I) for all of the heteroaromatic compounds listed in this study. Thus, the combined use of NMP and an increased amount of phosphine is important for promoting the reaction efficiently. The use of this general approach to rapid methylation has been well demonstrated by the synthesis of the PET tracers 2- and 3-[11C]methylpyridines by using [Pd2(dba)3]/P(o-CH3C6H 4)3/CuBr/CsF (1:16:2:5) in NMP at 60°C for 5 min, which gives the desired products in HPLC analytical yields of 88 and 91%, respectively.

Palladium(0)-mediated rapid methylation and fluoromethylation on carbon frameworks by reacting methyl and fluoromethyl iodide with aryl and alkenyl boronic acid esters: Useful for the synthesis of [11C]CH 3-C-and [18F]FCH2-C-containing PET tracers (PET = positron emission tomography)

The rapid methylation and fluoromethylation on aryl and alkenyl carbon frameworks by reacting methyl and fluoromethyl iodide with aryl and alkenyl boronates have been studied with the focus on the realization of the synthesis of [11C]CH3- and [18F]FCH2-labeled positron emission tomography (PET) tracers. The coupling of methyl iodide and pinacol phenylboronate (40 equiv) is accomplished in > 91% yield within 5 min at 60 °C under the conditions of [Pd2(dba)3]/P(o- CH3C6H4)3/K2CO 3 (0.5:2:2; dba = di-benzylideneacetone) in DMF. The reaction shows a high generality and is applicable to various types of aryl and alkenyl boronates, giving the corresponding methylated derivatives in high yields (80-99). This reaction is also useful for the rapid incorporation of the fluoromethyl group. Thus, this boron protocol provides a firm chemical basis for the synthesis of 11C- and 18F-incorporated PET tracers and can be used as a complementary method for [11C]methylation together with our previous and ongoing processes using organotributylstannanes.

METHOD OF RAPID METHYLATION, KIT FOR PREPARING PET TRACER AND METHOD OF PRODUCING PET TRACER

It is intended to provide a method of rapid methylation of an aromatic compound or an alkenyl compound, which is capable of obtaining an aromatic compound or an alkenyl compound labeled with a methyl group or a fluoromethyl group under a mild condition rapidly in high yield using an organic boron compound whose toxicity is not so high as a substrate; a kit for preparing a PET tracer to be used in the same, and a method of producing a PET tracer using the same. In an aprotic polar solvent, methyl iodide or X-CH2F (wherein X is a functional group which can be easily released as an anion), an organic boron compound in which an aromatic ring or an alkenyl group is attached to boron are subjected to cross-coupling in the presence of a palladium(0) complex, a phosphine ligand, and a base.

5-Substituted isoquinoline derivatives

A compound represented by the following formula (1) or a salt thereof: wherein R1 represents hydrogen atom, a halogen atom and the like; R2 represents hydrogen atom, a halogen atom, a C1-6 alkyl group and the like; and R3 represents —O—X—C(A1)(A11)—C(A2)(A2l)—N(A3l)(A3)(X represents propylene group etc., A11 and A21 represent hydrogen atom, or a C1-6 alkyl group, A31 represents a C1-6 alkyl group substituted with hydroxyl group, or hydrogen atom, and A1, A2, and A3 represent hydrogen atom, a C1-6 alkyl group and the like) and the like, which has an inhibitory activity on the phosphorylation of myosin regulatory light chain, and is useful for treatment of diseases relating to contraction of various cells and the like.