Efficient Synthesis of 2-Aryl-6-chloronicotinamides via PXPd2-Catalyzed Regioselective Suzuki Coupling

Yang, Wu; Wang, Yufeng; Corte, James R.

doi:10.1021/ol035188g

Cited by 69 publications

(42 citation statements)

References 15 publications

(9 reference statements)

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“…For the synthesis of JKJ05, (S)-(-)-2-amino-3-phenyl-1-propanol (45 mg, 0.30 mmol) and potassium tert-butoxide (34 mg, 0.30 mmol) were added to a solution of the appropriately substituted 2-chloropyridine (88 mg, 0.20 mmol) (prepared in accordance with known literature methods (20)) in toluene (2.5 ml), and the resulting mixture was stirred for 48 h at 90°C. The solution was allowed to cool to room temperature, and the solvent was removed under reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

A Missense Mutation in the Seven-transmembrane Domain of the Human Ca2+ Receptor Converts a Negative Allosteric Modulator into a Positive Allosteric Modulator

Jiang

Costanzi

et al. 2006

Journal of Biological Chemistry

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G protein-coupled receptors (GPCRs) are the most common targets of drug action. Allosteric modulators bind to the seven-transmembrane domain of family 3 GPCRs and offer enhanced selectivity over orthosteric ligands that bind to the large extracellular N terminus. We characterize a novel negative allosteric modulator of the human Ca 2؉ receptor, Compound 1, that retains activity against the E837A mutant that lacks a response to previously described positive and negative modulators. A related compound, JKJ05, acts as a negative allosteric modulator on the wild type receptor but as a positive modulator on the E837A mutant receptor. This positive modulation critically depends on the primary amine in JKJ05, which appears to interact with acidic residue Glu 767 in our model of the seven-transmembrane domain of the receptor. Our results suggest the need for identification of possible genetic variation in the allosteric site of therapeutically targeted GPCRs.

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Section: Methodsmentioning

confidence: 99%

A Missense Mutation in the Seven-transmembrane Domain of the Human Ca2+ Receptor Converts a Negative Allosteric Modulator into a Positive Allosteric Modulator

Jiang

Costanzi

et al. 2006

Journal of Biological Chemistry

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“…In 2003, Yang and coworkers reported an example of site-selectivity switching in the Suzuki-Miyaura coupling of 2,6-dichloropyridine derivatives 30 with phenylboronic acid (31) ( Table 3) [36]. When Pd(PPh 3 ) 4 was used as the catalyst, 30 (R = OMe) was preferentially converted to 33, in which the phenyl group was introduced at the less hindered C6 position (Entry 1, Table 3).…”

Section: Pyridine Derivativesmentioning

confidence: 99%

Catalyst-Controlled Site-Selectivity Switching in Pd-Catalyzed Cross-Coupling of Dihaloarenes

Manabe

Yamaguchi

2014

Catalysts

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Pd-catalyzed, site-selective mono-cross-coupling of substrates with two identical halo groups is a useful method for synthesizing substituted monohalogenated arenes. Such arenes constitute an important class of compounds, which are commonly identified as drug components and synthetic intermediates. Traditionally, these site-selective reactions have been realized in a "substrate-controlled" manner, which is based on the steric and electronic differences between the two carbon-halogen bonds of the substrate. Recently, an alternative strategy, "catalyst-controlled" site-selective cross-coupling, has emerged. In this strategy, the preferred reaction site of a dihaloarene can be switched, merely by changing the catalyst used. This type of selective reaction further expands the utility of Pd-catalyzed cross-coupling. In this review, we summarize the reported examples of catalyst-controlled site-selectivity switching in Pd-catalyzed cross-coupling of dihaloarenes.

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“…Addition of CNTs can not only improve its mechanical properties but also modify its electrical properties and help with a problem of electromagnetic interference shielding. [15][16][17] …”

Section: Introductionmentioning

confidence: 99%

Carbon Nanotubes Functionalized in Oxygen and Water Low Pressure Discharges used as Reinforcement of Polyurethane Composites

Zajı́čková

Kučerová

Buršı́ková

et al. 2009

Plasma Processes & Polymers

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The functionalization of multi‐walled CNTs in O2/Ar and H2O/Ar low pressure capacitive discharges was studied by XPS and FT‐IR. The pristine and functionalized CNTs were used as fillers in polyurethane paints. Successful plasma functionalization was confirmed by changes in atomic composition and chemical shift of the XPS atomic signals. The functionalization was indicated also by the shift of IR absorption peaks corresponding to the motion of carbon skeleton, especially the peak at about 1 560 cm−1. The presence of carbonyl was confirmed by IR absorption peak at 1 723 cm−1 only for O2/Ar plasma. The plasma functionalized CNTs increased significantly the universal and plastic hardness of the CNTs reinforced polyurethane as compared to the composites with pristine CNTs.

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Efficient Synthesis of 2-Aryl-6-chloronicotinamides via PXPd2-Catalyzed Regioselective Suzuki Coupling

Cited by 69 publications

References 15 publications

A Missense Mutation in the Seven-transmembrane Domain of the Human Ca2+ Receptor Converts a Negative Allosteric Modulator into a Positive Allosteric Modulator

A Missense Mutation in the Seven-transmembrane Domain of the Human Ca2+ Receptor Converts a Negative Allosteric Modulator into a Positive Allosteric Modulator

Catalyst-Controlled Site-Selectivity Switching in Pd-Catalyzed Cross-Coupling of Dihaloarenes

Carbon Nanotubes Functionalized in Oxygen and Water Low Pressure Discharges used as Reinforcement of Polyurethane Composites

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