Journal of Heterocyclic Chemistry published new progress about 847818-64-8. 847818-64-8 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Pyrazole,Boronic Acids,Boronic acid and ester, name is (1-Isobutyl-1H-pyrazol-5-yl)boronic acid, and the molecular formula is C7H13BN2O2, Quality Control of 847818-64-8.
Ivachtchenko, Alexandre V. published the artcileSynthesis of pinacol esters of 1-alkyl-1H-pyrazol-5-yl- and 1-alkyl-1H-pyrazol-4-ylboronic acids, Quality Control of 847818-64-8, the publication is Journal of Heterocyclic Chemistry (2004), 41(6), 931-939, database is CAplus.
1-Substituted pyrazolylboronic acids and their pinacol esters were prepared by lithiation-borylation reaction sequence starting from bromopyrazoles. Alkylation of 4-bromo-1H-pyrazole gave 1-alkyl-4-bromo-1H-pyrazoles, which were lithiated at -80° and borylated with B(OMe)3 to give 1-R-1H-pyrazole-4-boronic acids [4a–g, R = Me, Et, Pr, (CH2)2CHMe2, (CH2)2OMe, (CH2)3NMe2, (CH2)2CH(OEt)2]. Lithiation of 4-bromo-1-(2-dimethylaminoethyl)-1H-pyrazole (2h) gave 5-lithio-derivative, which on borylation afforded 1-R1-4-Br-1H-pyrazole-5-boronic acid (8). Boronic acids 4a–g are unstable and were deborylated slowly due to hydrolysis by traces of water; the stability of boryl derivatives can be greatly enhanced by converting to corresponding pinacol boronates (10a–g). Direct lithiation of 1-R2-1H-pyrazoles by BuLi at -20° afforded 5-lithio-derivatives, which were converted to corresponding 1-R2-1H-pyrazole-5-boronic acids [17a–e; R2 = Me, iBu, Pr, (CH2)2CHMe2, (CH2)2CH(OEt)2] and their pinacol boronates (18a–e, same R2). The key step in the described methodol. is the regioselective lithiation of the pyrazole ring. The synthesized pinacolates are stable under prolonged storage and can be used as convenient reagents in organic synthesis.
Journal of Heterocyclic Chemistry published new progress about 847818-64-8. 847818-64-8 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Pyrazole,Boronic Acids,Boronic acid and ester, name is (1-Isobutyl-1H-pyrazol-5-yl)boronic acid, and the molecular formula is C7H13BN2O2, Quality Control of 847818-64-8.
Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics