An efficient synthesis of a highly functionalized 4-arylpiperidine

Boice, Geneviève N.; Savarin, Cécile; Murry, Jerry A.; Conrad, Kendon J.; Matty, Louis; Corley, Edward G.; Smitrovich, Jacqueline H.; Hughes, D. L.

doi:10.1016/j.tet.2004.09.092

Cited by 15 publications

(7 citation statements)

References 20 publications

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“…Selective bromination of 3-chlorobenzonitrile by 1,3-dibromo-5,5-dimethylhydantoin (DBH) gave 2-bromo-5-chlorobenzonitrile 19 as reported previously 22. Compound 19 was treated with various substituted aryl boronic acids under the Suzuki coupling condition to give a set of intermediates 20a-c , and final product 21 .…”

Section: Chemistrymentioning

confidence: 85%

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Structure–activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5

Zhang

Zou

Rodriguez

et al. 2010

Bioorganic & Medicinal Chemistry

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The metabotropic glutamate receptor subtype 5 (mGluR5) has been implicated in numerous neuropsychiatric disorders including addiction. We have discovered that the rigid diaryl alkyne template, derived from the potent and selective noncompetitive mGluR5 antagonist 2-methyl-6-(phenylethynyl)pyridine (MPEP), can serve to guide the design of novel quinoline analogues and pharmacophore optimization has resulted in potent mGluR5 noncompetitive antagonists (EC 50 range 60-100 nM) in the quinoline series.

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Section: Chemistrymentioning

confidence: 85%

“… a Reagents and conditions: (a) DBH, H 2 SO 4 , TFA;22 (b) Na 2 CO 3 , Pd(PPh 3 ) 4 , DME, H 2 O, 70 °C, overnight; (c) K 3 PO 4 , Pd(OAc) 2 , ligand 1L , dioxane, H 2 O, 105 °C, 16–20 h…”

Section: Figures and Tablementioning

confidence: 99%

Structure–activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5

Zhang

Zou

Rodriguez

et al. 2010

Bioorganic & Medicinal Chemistry

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“…Bromination of 3-chlorobenzonitrile 148 with 1,3-dibromo-5,5-dimethylhydantoin 149 according to the literature procedure afforded aryl bromide 150 . 90 A Suzuki coupling with boronic acids 151–153 gave the biaryl products 154–156 . A second Suzuki coupling between the aryl chloride and boronate ester 158 was accomplished in the presence of phosphine ligand 157 to afford the final products 159–161 .…”

Section: National Institute On Drug Abusementioning

confidence: 99%

Recent Advances in the Design and Development of Novel Negative Allosteric Modulators of mGlu₅

Emmitte

2011

ACS Chem. Neurosci.

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Negative allosteric modulators (NAMs) of metabotropic glutamate receptor subtype 5 (mGlu5) have remained attractive to researchers as potential therapies for a number of central nervous system related diseases, including anxiety, pain, gastroesophageal reflux disease (GERD), addiction, Parkinson's disease (PD), and fragile X syndrome (FXS). In addition to the many publications with supportive preclinical data with key tool molecules, recent positive reports from the clinic have bolstered the confidence in this approach. During the two year time span from 2009 through 2010, a number of new mGlu5 NAM chemotypes have been disclosed and discussed in the primary and patent literature. A summary of several efforts representing many diverse chemotypes are presented here, along with a discussion of representative structure activity relationships (SAR) and synthetic approaches to the templates where possible.

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“…The reaction of 4-iodopyridine with 2-iodothiophene under the action of hydrazine hydrate in an alkaline media was promoted by palladium amalgam to yield 4-(2-thienyl)pyridine (103). 150 In the presence of palladium(II) chloride in combination with tetrakis(dimethylamino)ethylene (TDAE), 4-chloropyridine was converted into 4,4 H -bipyridyl (142) under rather mild conditions (50 8C). 151 If in this reaction, 4-bromopyridine hydrochloride was substituted for 4-chloropyridine, the product yield increased to 92%.…”

Section: G Miscellaneous Coupling Reactions Catalysed By Palladium Amentioning

confidence: 99%

Advances in the synthesis of 4-aryl- and 4-hetarylpyridines

Gromov¹,

Fomina²

2008

Russ. Chem. Rev.

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Information on the methods of synthesis of 4-aryl-Information on the methods of synthesis of 4-arylor 4-hetaryl-substituted pyridines developed in the recent or 4-hetaryl-substituted pyridines developed in the recent years is discussed and generalised. Examples of the practical years is discussed and generalised. Examples of the practical use of 4-(het)arylpyridine derivatives are given. The biblio-use of 4-(het)arylpyridine derivatives are given. The bibliography includes 166 references graphy includes 166 references. .

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An efficient synthesis of a highly functionalized 4-arylpiperidine

Cited by 15 publications

References 20 publications

Structure–activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5

Structure–activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5

Recent Advances in the Design and Development of Novel Negative Allosteric Modulators of mGlu₅

Advances in the synthesis of 4-aryl- and 4-hetarylpyridines

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An efficient synthesis of a highly functionalized 4-arylpiperidine

Cited by 15 publications

References 20 publications

Structure–activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5

Structure–activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5

Recent Advances in the Design and Development of Novel Negative Allosteric Modulators of mGlu5

Advances in the synthesis of 4-aryl- and 4-hetarylpyridines

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Product

Resources

About

Recent Advances in the Design and Development of Novel Negative Allosteric Modulators of mGlu₅