35421-09-1

Basic information

• Product Name: Methanone, (4-methoxyphenyl)(1-methyl-1H-pyrrol-2-yl)-
• CAS NO: 35421-09-1
• Molecular Formula: C13H13NO2
• Molecular Weight: 215.252
• Mol File: 35421-09-1.mol

Chemical Properties

• CAS DataBase Reference: Methanone, (4-methoxyphenyl)(1-methyl-1H-pyrrol-2-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, (4-methoxyphenyl)(1-methyl-1H-pyrrol-2-yl)-(35421-09-1)
• EPA Substance Registry System: Methanone, (4-methoxyphenyl)(1-methyl-1H-pyrrol-2-yl)-(35421-09-1)

Safety Data

• Hazardous Substances Data: 35421-09-1(Hazardous Substances Data)

Upstream product

• 96-54-8 N-Methylpyrrole 
• 201230-82-2 carbon monoxide 
• 696-62-8 para-iodoanisole 
• 66107-29-7 4-methoxyphenyl triflate 
• 874-90-8 4-methoxybenzonitrile 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 93303-99-2 <(1-methyl-2-pyrrolyl)carbonyl>trimethylsilane 
• 58948-36-0 2-(4-Methoxyphenyl)-1,3-benzoxathiolium tetrafluoroborate 
• 100-07-2 4-methoxy-benzoyl chloride 
• 112925-41-4 2-[2-(4-Methoxy-phenyl)-benzo[1,3]oxathiol-2-yl]-1-methyl-1H-pyrrole 

Downstream Products

• 157847-09-1 2-Chloro-1-[5-(4-methoxy-benzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone 

Relevant articles and documents

Palladium catalyzed carbonylative generation of potent, pyridine-based acylating electrophiles for the functionalization of arenes to ketones

We describe here the design of a palladium catalyzed route to generate aryl ketones via the carbonylative coupling of (hetero)arenes and aryl- or vinyl-triflates. In this, the use of the large bite angle Xantphos ligand on palladium provides a unique avenue to balance the activation of the relatively strong C(sp2)-OTf bond with the ultimate elimination of a new class of potent Friedel-Crafts acylating agent: N-acyl pyridinium salts. The latter can be exploited to modulate reactivity and selectivity in carbonylative arene functionalization chemistry, and allow the efficient synthesis of ketones with a diverse array of (hetero)arenes. This journal is

An Electrophilic Approach to the Palladium-Catalyzed Carbonylative C-H Functionalization of Heterocycles

A palladium-catalyzed approach to intermolecular carbonylative C-H functionalization is described. This transformation is mediated by PtBu3-coordinated palladium catalyst and allows the derivatization of a diverse range of heterocycles, including pyrroles, indoles, imidazoles, benzoxazoles, and furans. Preliminary studies suggest that this reaction may proceed via the catalytic formation of highly electrophilic intermediates. Overall, this provides with an atom-economical and general synthetic route to generate aryl-(hetero)aryl ketones using stable reagents (aryl iodides and CO) and without the typical need to exploit pre-metalated heterocycles in carbonylative coupling chemistry.

Acylation of pyrroles and their free (N-H)-derivatives via palladium-catalyzed carbopalladation of nitriles

An efficient regioselective synthesis of 2-acylpyrroles via palladium-catalyzed addition of pyrroles with benzonitriles and subsequent hydrolysis is developed. The direct acylation reaction of protected as well as (NH)-free pyrroles proceeded smoothly to

Iodide as an activating agent for acid chlorides in acylation reactions

Acid chlorides can be activated using a simple iodide source to undergo nucleophilic attack from a variety of relatively weak nucleophiles. These include Friedel-Crafts acylation of N-methylpyrroles, N-acylation of sulfonamides, and acylation reactions of hindered phenol derivatives. The reaction is believed to proceed through a transient acid iodide intermediate.

Reversed-polarity synthesis of diaryl ketones via palladium-catalyzed cross-coupling of acylsilanes

Acylsilanes serve as acyl anion equivalents in a palladium-catalyzed cross-coupling reaction with aryl bromides to give unsymmetrical diaryl ketones. Water plays a unique and crucial activating role in these reactions. High-throughput experimentation techniques provided successful reaction conditions initially involving phosphites as ligands. Ultimately, 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane was identified as giving a longer-lived catalyst with higher turnover numbers. Its use, in conjunction with a palladacycle precatalyst, led to optimal reaction rates and yields. Scope and limitations of this novel method are presented along with initial mechanistic insight.

Friedel - Crafts acylation of pyrroles and indoles using 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) as a nucleophilic catalyst

1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) has been shown to be an effective catalyst for the regioselective Friedel - Crafts C-acylation of pyrroles and indoles in high yields. A detailed mechanistic study implies that DBN is acting as a nucleophilic organocatalyst, with the X-ray crystal structure of a key N-acyl-amidine intermediate having been determined for the first time.

Aroyl aminoacyl pyrroles for use in the treatment of neuropathic pain

Aroyl aminoacyl pyrroles are pharmaceutically useful in treating neuropathic pain, which includes utility for the treatment of neuropathic pain.

Aroyl(aminoacyl)pyrroles, a new class of anticonvulsant agents

2-Aroyl-4-(ω-aminoacyl)- (4) and 4-aroyl-2-(ω-aminoacyl)pyrroles (9) represent a new, structurally novel class of anticonvulsant agents. Compounds of type 4 were prepared by Friedel-Crafts acylation of a 2-aroylpyrrole with an ω-chloroacyl chloride followed by displacement of the chloro group by a primary or secondary amine. Compounds of type 9 were prepared by Friedel- Crafts aroylation of a 2-(ω-chloroacyl)pyrrole followed by displacement by an amine. These compounds were active in the mouse and rat maximal electroshock tests but not in the mouse metrazole test. The lead compound, RWJ-37868, 2-(4-chlorobenzoyl)-4-(1-piperidinyl-acetyl)-1,3,5- trimethylpyrrole (4d), showed potency and therapeutic index comparable to those of phenytoin and carbamazepine and greater than those of sodium valproate. This compound blocked bicuculline induced seizures, did not elevate seizure threshold following iv infusion of metrazole, and blocked influx of Ca2+ ions into cerebellar granule cells induced by K+ or veratridine.

Acylation of Pyrrole and N-Methylpyrrole with 1,3-Benzoxathiolium Tetrafluroborates. A High-Yield Method for the Synthesis of Diacylpyrroles

2-Substituted 1,3-benzoxathiolium tetrafluoroborates (I) were used as masked acylating agents for pyrrole and N-methylpyrrole.The reactions on pyrrole (II) were regiospecific, and according to the molar ratio of the reagents (I:II = 1:3 or 2.5-3:1), 2-acylpyrroles were obtained in moderate to good yields (38-82percent) and 2,5-diacylpyrroles were obtained in excellent yields (in most cases, quantitative).The reactions on N-methylpyrrole (III) were not regioselective, and both α- and β-positions were attacked.So, depending on the molar ratio of the reagents (I:III = 1:3 or 2,5-3:1), 2- and 3-acyl-N-methylpyrroles (9-51percent and 27-68percent yields, respectively) and 2,4- and 2,5-diacyl-N-methylpyrroles (60-93percent and 17-40percent, respectively) were obtained.A very interesting feature of the new method is the possibility of introducing two identical or different acyl groups in the pyrrole ring under mild conditions. 1H and 13C NMR spectra of all the new compounds and IR spectra, recorded in the gas phase, of 2- and 3-acylpyrroles and of 2,4- and 2,5-diacylpyrroles are reported.