- meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation
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Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.
- Li, Xuejing,Deng, Xingwang,Coyne, Anthony G.,Srinivasan, Rajavel
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supporting information
p. 8018 - 8023
(2019/05/29)
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- No-carrier-added [18F]fluoroarenes from the radiofluorination of diaryl sulfoxides
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No-carrier-added [18F]fluoroarenes were synthesized through the radiofluorination of diaryl sulfoxides with [18F]fluoride ion. Diaryl sulfoxides bearing a para electron-withdrawing substituent readily gave the corresponding 4-[18F]fluoroarenes in high RCYs. This process broadens the scope for preparing novel 18F-labeling synthons and PET radiotracers.
- Chun, Joong-Hyun,Morse, Cheryl L.,Chin, Frederick T.,Pike, Victor W.
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supporting information
p. 2151 - 2153
(2013/03/14)
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- Glucagon Receptor Modulators
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The present invention provides a compound of Formula (I) or a pharmaceutically acceptable salt thereof wherein R1, R2, R3, A1, A2, A3, A4, L, B1, B2, B3 and B4 are as defined herein. The compounds of Formula I have been found to act as glucagon antagonists or inverse agonists. Consequently, the compounds of Formula I and the pharmaceutical compositions thereof are useful for the treatment of diseases, disorders, or conditions mediated by glucagon.
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Page/Page column 38
(2012/07/13)
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- Glucagon Receptor Antagonists, Preparation and Therapeutic Uses
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The present invention discloses novel compounds of Formula I, or pharmaceutically acceptable salts thereof, which have glucagon receptor antagonist or inverse agonist activity, as well as methods for preparing such compounds. In another embodiment, the in
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Page/Page column 12
(2009/01/20)
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- Aryl sulfonamide and sulfonyl compounds as modulators of PPAR and methods of treating metabolic disorders
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Aryl sulfonamide and sulfonyl compounds as modulators of peroxisome proliferator activated receptors, pharmaceutical compositions comprising the same, and methods of treating disease using the same are disclosed.
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Page/Page column 94
(2010/02/14)
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- Diphenylmethane derivatives
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The invention relates to novel diphenylmethane derivatives, processes for their preparation and their use in medicaments, in particular for the indications of arteriosclerosis and hypercholesterolaemia.
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- PROTON TRANSFER REACTIONS BETWEEN ORTHO-METHYL SUBSTITUTED DERIVATIVES OF 4-NITROPHENYLPHENYLCYANOMETHANE AND NITROGEN BASES IN ACETONITRILE SOLVENT
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Equilibrium constants, rate constants, primary deuterium isotope effects, and activation parameters have been measured for the proton transfer reactions in acetonitrile solvent of 4-nitrophenylphenylcyanomethane and 2-methyl-4-nitrophenylphenylcyanomethane with tetramethylguanidine base and for the reactions of 2-methyl-4-nitrophenylphenylcyanomethane and 2,6-dimethyl-4-nitrophenylphenylcaynomethane with 1,5-diazabicycloundec-7-ene base.Introduction of the ortho-methyl groups in the substrate molecule caused significant reductions in the equilibrium and the rate constants.The expected rise in the kinetic primary deuterium isotope effect was not observed when the first ortho-methyl group was introduced, but a 20percent increase did accompany the introduction of the second ortho-methyl group.Enthalpy of activation measurements indicated that there was no increase in the proton tunnelling contribution to the isotope effect when the amount of steric hindrance is increased with ortho-methyl groups.
- Leffek, Kenneth T.,Pruszynski, Przemyslaw
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p. 1454 - 1458
(2007/10/02)
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