345-35-7Relevant academic research and scientific papers
Synthesis of mono- and difluorobenzyl chlorides by chlorination of mono- and difluorotoluenes with CCl4 and t-BuOCl induced by iron-containing catalysts
Bayguzina, Alfiya R.,Gallyamova, Leysan I.,Khalilov, Leonard M.,Khusnutdinov, Ravil I.
, (2019)
Mono- and difluorobenzyl chlorides were synthesized by chlorination of mono- and difluorotoluenes with CCl4?MeOH or t-BuOCl in the presence of iron-containing catalysts.
FLUOROINDOLE DERIVATIVES AS MUSCARINIC M1 RECEPTOR POSITIVE ALLOSTERIC MODULATORS
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Page/Page column 25; 26, (2017/03/28)
The present invention relates to compound of formula (I), or stereoisomers and pharmaceutically acceptable salts as muscarinic M1 receptor positive allosteric modulators. This invention also relates to methods of making such compounds and pharmaceutical compositions comprising such compounds. The compounds of this invention are useful in the treatment of various disorders that are related to muscarinic M1 receptor.(Formula I) (I)
Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers
Huy, Peter H.,Motsch, Sebastian,Kappler, Sarah M.
supporting information, p. 10145 - 10149 (2016/08/16)
A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.
2-silyloxy-tetrahydrothienopyridine, salt thereof and process for preparing the same
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, (2008/06/13)
A 2-silyloxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine represented by the formula (I): STR1 wherein R 1, R 2 and R 3 each independently represent an alkyl group having 1 to 10 carbon atoms or an aryl group,and a salt thereof and a process for preparing the same, and a 5-alkyl-2-silyloxy-4,5,6,7-tetrahydrothieno[3,2-c]-pyridine represented by the formula (IV): STR2 wherein R 1, R 2 and R 3 represent the same meanings as described above; R 4 represents a hydrogen atom, an alkoxycarbonyl group having 2 to 10 carbon atoms, an acyl group having 2 to 10 carbon atoms or a cyclo-alkylcarbonyl group having 4 to 10 carbon atoms; andR 5 represents a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms,which is useful as a synthetic intermediate of an antiplatelet medicine and an elastase inhibitor, etc., and a process for preparing the same.
Kinetics and Equilibria of Chloride Transfer Reactions. Stabilities of Carbocations Based on Chloride and Hydride Transfer Equilibria Measurements
Sharma, R. B.,Sharma, D. K. Sen,Hiraoka, K.,Kebarle, P.
, p. 3747 - 3757 (2007/10/02)
The kinetics of a number of gas-phase chloride transfer reactions R0(1+)+RCl=R0Cl+R(1+) were measured with a pulsed electron high pressure mass spectrometer.Most of the reactions were found to occur near the collision limit, i.e., with rate constants k ca. 10-9 molecules-1 cm3 s-1.However, several reactions were much slower and were exhibiting negative temperature dependence, i.e., decreasing rate with increasing temperature.Hydride and chloride transfer equilibria were determined for various carbocations R(1+) (R=isopropyl, cyclopentyl, tert-butyl, 1-methylcyclopentyl, substituted benzyls, norbornyl, 2-methyl-2-norbornyl, and adamantyl).Excellent agreement with earlier hydride transfer measurements of Solomon, Meot-Ner, and Field were observed.The chloride affinities generally support conclusions based on the hydride transfer data.Discussion of the data in connection with benzyl cation substituent effects, the norbornyl cation stability, and solvent effects on carbocation stability is presented.The data show that the 2-norbornyl cation is unusually stable.Significant differences between carbocation R(1+) stabilities in gas phase and solution are found which suggest that both differential nucleophilic solvent stabilization and differential nonspecific solvation occur in solution.
