5415-11-2

Upstream product

• 121-98-2 methyl 4-methoxybenzoate 
• 108-86-1 bromobenzene 
• 3672-47-7 3-oxo-3-(4'-methoxyphenyl)propanenitrile 
• 93011-61-1 3-(4-methoxyphenyl)-3-oxo-2-phenylpropanal 
• 1023-17-2 4-methoxyphenyl benzyl ketone 
• 140-29-4 phenylacetonitrile 
• 94-30-4 ethyl 4-methoxybenzoate 
• 116485-64-4 5-(4-methoxyphenyl)-4-phenylisoxazole 

Downstream Products

• 17828-67-0 5-methoxy-2-phenyl-1H-indene-1,3(2H)-dione 
• 805238-99-7 2,3-bis(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine 
• 805238-97-5 2-(4-methoxyphenyl)-3-phenylpyrazolo[1,5-a]pyrimidine 
• 802919-04-6 5-(4-methoxy-phenyl)-4-phenyl-1H-pyrazol-3-ylamine 
• 199987-33-2 3-amino-2-phenyl-5-methoxy-1-indenone 

Relevant academic research and scientific papers

Preparation of 3,4-Substituted-5-Aminopyrazoles and 4-Substituted-2-Aminothiazoles

3,4-Substituted-5-aminopyrazoles and 4-substituted-2-aminothiazoles are frequently used intermediates in medicinal chemistry and drug discovery projects. We report an expedient flexible synthesis of 3,4-substituted-5-aminopyrazoles (35 examples), based on palladium-mediated α-arylation of β-ketonitriles with aryl bromides. A library of 4-substituted-2-aminothiazoles (21 examples) was assembled by a sequence employing Suzuki coupling of newly prepared, properly protected pinacol ester and MIDA ester of 4-boronic acid-2-aminothiazole with (hetero)aryl halides.

Pyrazolo[1,5-a]pyrimidines as estrogen receptor ligands: Defining the orientation of a novel heterocyclic core

We investigated the pyrazolo[1,5-a]pyrimidine system as a novel heterocyclic scaffold for the development of estrogen receptor (ER) ligands. By altering the pattern of hydroxyl substitution, we established the orientation that is most favorable for ER bin

Enolate Ions as ss-Activators of ortho-metalation: Direct Synthesis of 3-Aminoindenones

ss-Ketonitriles derived from a Claisen condensation of benzoate esters with alkyl- or phenylacetonitriles lead to 3-aminoindenones in the presence of excess LDA. This new reaction is also applicable to pyridine carboxylic esters. All of the 3-aminoindenones and their aza analogues can be hydrolyzed by acid to give the corresponding 1,3-indandiones. The mechanism of the reaction falls into the directed-ortho-metalation class in which the initial enolate ion of the keto-nitrile directs self-metalation at an ortho position. The new anion then cyclizes onto the nitrile group to generate an aminoindenone. Surprisingly the simplest member of the series, benzoylacetonitrile, does not undergo cyclization. Mechanistic isotope studies revealed that this substance preferentially and directly forms a dianion on the side chain, which is not further deprotonated at the ortho position of the aromatic ring.

A new anionic cyclization reaction: Condensation of benzoate esters with nitriles to give 3-amino-2-inden-1-ones

A new type of anionic cyclization has been discovered in which the condensation of alkyl benzoates with simple nitriles, induced by an excess of LDA, leads directly to substituted-3-amino-1-ones. The corresponding intermediate β-oxonitriles undergo cyclization to give, in most instances, superior yields of the same compounds. Acid hydrolysis of these indenones leads in high yield to the corresponding biologically active (anticoagulant) indandiones.