185220-68-2Relevant articles and documents
Fully regiocontrolled polyarylation of pyridine
Doebelin, Christelle,Wagner, Patrick,Bihel, Frederic,Humbert, Nicolas,Kenfack, Cyril Assongo,Mely, Yves,Bourguignon, Jean-Jacques,Schmitt, Martine
, p. 908 - 918 (2014/03/21)
Starting from commercially available 2-chloro-3-hydroxypyridine, a new route leading to the first protypical pentaarylpyridine bearing five different substituents is reported. This strategy involves a set of five sequential but fully regiocontrolled Suzuki-Miyaura reactions and highlights the 2-OBn pyridine protecting group as a key intermediate. The 2-OBn group played a double role: (i) it allowed additional bromination at position 5 and (ii) it could afford the reactive OTf species for the last C-arylation step at the less hindered 2 position of the tetraarylpyridine. The photophysical properties of the novel compounds are also described. The synthesized pentaarylpyridine derivative exhibit a large Stokes shift, strong solvatochromism, and quantum yield values up to 0.47; thus, they constitute promising building blocks for the design of environment-sensitive probes.
Inhibitors of α4β1 mediated cell adhesion
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Page/Page column 123, (2010/02/05)
The present invention relates to compound of formula (I), that are potent inhibitors of α4β1mediated adhesion to either VCAM or CS-1 and which could be useful for the treatment of inflammatory diseases. Specifically, the molecules of the present invention can be used for treating or preventing α4β1adhesion mediated conditions in a mammal such as a human. This method may comprise administering to a mammal or a human patient an effective amount of the compound or composition as explained in the present specification.
Asymmetric synthesis of β-pyridyl-β-amino acid derivatives
Bull, Steven D.,Davies, Stephen G.,Fox, David J.,Gianotti, Massimo,Kelly, Peter M.,Pierres, Camille,Savory, Edward D.,Smith, Andrew D.
, p. 1858 - 1868 (2007/10/03)
The conjugate additions of homochiral lithium (R)-N-benzyl-N-α-methyl-4-methoxybenzylamide to tert-butyl 3-(3-pyridyl)- and tert-butyl 3-(4-pyridyl)-prop-2-enoates proceed in 84% de, and after subsequent recrystallisation and oxidative N-deprotection furnish the (S)-3-(3-pyridyl)- and (S)-3-(4-pyridyl)-β-amino acid derivatives in 97% ee and 98% ee respectively. Conjugate additions of lithium N-benzyl-N-α-methyl-4-methoxybenzylamide to tert-butyl 3-(2-pyridyl)prop-2-enoates proceed with low levels of diastereoselectivity unless the 3-(2-pyridyl) ring is substituted. Application of this methodology allows the asymmetric synthesis of (R)-tert-butyl 3-(2-chloro-3-methoxymethoxy-6-pyridyl)-3-aminopropanoate, the protected β-amino ester component of kedarcidin, in 97% ee.