- Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis
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The kinetics and mechanism of the base-catalyzed hydrolysis (ArB(OR)2→ ArB(OH)2) and protodeboronation (ArB(OR)2→ ArH) of a series of boronic esters, encompassing eight different polyols and 10 polyfluoroaryl and heteroaryl moieties, have been investigated by in situ and stopped-flow NMR spectroscopy (19F,1H, and11B), pH-rate dependence, isotope entrainment,2H KIEs, and KS-DFT computations. The study reveals the phenomenological stability of boronic esters under basic aqueous-organic conditions to be highly nuanced. In contrast to common assumption, esterification does not necessarily impart greater stability compared to the corresponding boronic acid. Moreover, hydrolysis of the ester to the boronic acid can be a dominant component of the overall protodeboronation process, augmented by self-, auto-, and oxidative (phenolic) catalysis when the pH is close to the pKaof the boronic acid/ester.
- Hayes, Hannah L. D.,Wei, Ran,Assante, Michele,Geogheghan, Katherine J.,Jin, Na,Tomasi, Simone,Noonan, Gary,Leach, Andrew G.,Lloyd-Jones, Guy C.
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supporting information
p. 14814 - 14826
(2021/09/13)
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- Preparation method of mono-heterocyclic boric acid
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The invention provides a preparation method of mono-heterocyclic boric acid. The preparation method comprises steps as follows: (1) a compound shown in a formula I and alkyl borate are dissolved in asolvent A, and a liquor A is obtained; an organic lithium reagent is dissolved in a solvent B, and a liquor B is obtained; the liquor A and the liquor B are subjected to a continuous feeding reaction,the reaction is ended after a product flows out of a reaction pipe, and an intermediate is obtained; (2) the intermediate obtained in the step (1) is subjected to a hydrolysis reaction, and mono-heterocyclic boric acid is obtained. According to the provided preparation method, the reaction yield can be increased and can be up to 95% or above, the reaction time is shortened, the reaction can be completed within 5-60 min, the reaction temperature can be increased, energy consumption of the low-temperature reaction is reduced, the temperature is controllable, the safety is improved, the pressureis convenient to control, the automation degree is improved, production operation is facilitated, the cost is reduced, and the economic benefits are improved.
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Paragraph 0062; 0064
(2018/09/13)
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- 4-(8-METHOXY-1-((1-METHOXYPROPAN-2-YL)-2-(TETRAHYDRO-2H-PYRAN-4-YL)-1 H-IMIDAZO[4,5-C]QUINOLIN-7-YL)-3,5-DIMETHYLISOXAZOLE AND ITS USE AS BROMODOMAIN INHIBITOR
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Novel quinoline compounds of formula (I), pharmaceutical compositions containing such compounds and their use in therapy, as bromodomain inhibitors.
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Page/Page column 8
(2013/03/26)
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- AGONISTS OF GPR40
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The present invention relates to compounds that have the ability to modulate the activity of GPR40 and are there-fore useful in the treatment of GPR40 related disorders. In addition the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders related to GPR40 activity.
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Page/Page column 148-149
(2012/02/05)
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- Synthesis of 4-isoxazoleboronic acids: A new route to 4-isoxazolones
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4-Isoxazoleboronic acids have been prepared by interaction of 4-isoxazolylmagnesium iodides with trimethyl borate. Some of their reactions are described; in particular oxidative deboronation represents a new useful route to 4-isoxazolones.
- Cogoli, Augusto,Gruenanger, Paolo
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