872626-76-1Relevant articles and documents
Microwave synthesis method of 6-trifluoromethylpyridylaldehyde
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Paragraph 0033-0038; 0043-0048, (2021/01/20)
The invention relates to a microwave synthesis method of 6-trifluoromethylpyridylaldehyde. According to the method, a reaction is performed in a reaction tank by using a microwave irradiation technique; 1 eq of 6-trifluoromethylpyridinemethanol is added, a solvent is added to dissolve 6-trifluoromethylpyridinemethanol, 0.01-0.1 eq of a catalyst and 1-1.5 eq of an oxidant are added, microwave powerand temperature are set to react after feeding is finished, after the reaction is finished, rotary evaporation and concentration is performed on the reaction solution to obtain a solid product, and finally the solid product is separated and purified to obtain the 6-trifluoromethylpyridylaldehyde. Compared with the prior art, the method provided by the invention has the advantages of short reaction time, mild conditions, few side reactions and high yield, simplifies the production process, reduces the production cost and cycle, is easy to realize the popularization of industrial production, and is especially suitable for large-scale production of an intermediate 6-trifluoromethyl nicotinaldehyde of a colony stimulating factor 1 receptor (CSF-1R) inhibitor.
Visible-Light-Promoted Nickel- and Organic-Dye-Cocatalyzed Formylation Reaction of Aryl Halides and Triflates and Vinyl Bromides with Diethoxyacetic Acid as a Formyl Equivalent
Huang, He,Li, Xiangmin,Yu, Chenguang,Zhang, Yueteng,Mariano, Patrick S.,Wang, Wei
supporting information, p. 1500 - 1505 (2017/02/05)
A simple formylation reaction of aryl halides, aryl triflates, and vinyl bromides under synergistic nickel- and organic-dye-mediated photoredox catalysis is reported. Distinct from widely used palladium-catalyzed formylation processes, this reaction proceeds by a two-step mechanistic sequence involving initial in situ generation of the diethoxymethyl radical from diethoxyacetic acid by a 4CzIPN-mediated photoredox reaction. The formyl-radical equivalent then undergoes nickel-catalyzed substitution reactions with aryl halides and triflates and vinyl bromides to form the corresponding aldehyde products. Significantly, besides aryl bromides, less reactive aryl chlorides and triflates and vinyl halides serve as effective substrates for this process. Since the mild conditions involved in this reaction tolerate a plethora of functional groups, the process can be applied to the efficient preparation of diverse aromatic aldehydes.
Synthetic process of 6-(trifluoromethyl)pyridine-3-carboxaldehyde
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Paragraph 0011;, (2016/11/21)
The invention discloses a synthetic process of 6-(trifluoromethyl)pyridine-3-carboxaldehyde. The synthetic process comprises the following steps: under the protection of nitrogen, adding 1 eq of 2-trifluoromethyl-5-bromopyridine (calculated as the stoichiometric ratio) into a reaction vessel, dissolving with an organic solvent, controlling the temperature to be minus 20-10 DEG C, adding 1.0-5.0 eq of a stabilizer, dropwise adding 1.0-2.0 eq of a butyl lithium n-hexane solution while fully stirring, further adding 1.5-3.0 eq of dimethyl formamide, rising the temperature naturally, stirring overnight, and purifying the crude product by recrystallization. The synthetic process has the following positive effects: the activity of butyl lithium is partially reduced by adopting the stabilizer introducing method, the stability of the reaction at the intermediate state is improved, side reaction due to higher reaction temperature is inhibited, the reaction with dimethyl formamide is ensured, the yield is improved, problems in the prior art of high energy consumption and non-industrialization due to ultra-low temperature conditions are avoided at the same time, so that continuous production on general equipment can be achieved, the product quality is stable and reliable, and the purity can reach 98% or above.
Process for synthesizing 6-(trifluoromethyl)pyridine-3-carboxaldehyde
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Paragraph 0011, (2017/01/26)
The invention discloses a process for synthesizing 6-(trifluoromethyl)pyridine-3-carboxaldehyde. The process is characterized by comprising the following steps: under the protection of nitrogen, adding 2 eq of 5-bromo-2-(trifluoromethyl)pyridine in a stoichiometric ratio into a reaction container, dissolving with an organic solvent, controlling the temperature to be -20 DEG C to 10 DEG C, adding 1.0 to 3.0 eq of a stabilizer, dripping 1.0 to 3.0 eq of a butyllithium n-hexane solution with full stirring, then adding 1.5 to 3.0 eq of dimethylformamide, naturally heating up, stirring overnight, and recrystallizing and purifying a crude product. The process has the beneficial effects that by adopting a method of introducing the stabilizer, the activity of butyllithium is partially reduced, the stability of a reaction intermediate state is improved, happening of side reactions at higher reaction temperatures is inhibited, the reaction with the dimethylformamide is ensured, and the yield is improved; meanwhile, the problems of high energy consumption and no suitability for industrialization brought by ultralow temperatures in the prior art are avoided; and the product can be continuously produced on general equipment, the product quality is stable and reliable, and the purity reaches 98% or more.
Trifluoromethylation of (hetero)aryl iodides and bromides with copper(i) chlorodifluoroacetate complexes
Lin, Xiaoxi,Li, Zhengyu,Han, Xiaoyan,Weng, Zhiqiang
, p. 75465 - 75469 (2016/08/24)
A new copper-mediated trifluoromethylation reaction using copper(i) chlorodifluoroacetate complexes as reagents is reported. The complex [L2Cu][O2CCF2Cl] (L = bpy, dmbpy, phen) reacted with (hetero)aryl iodides and bromides in the presence of CsF in DMF at 75 °C to afford the trifluoromethylarenes in good to excellent yields. High compatibility with various chemical functions or (hetero)cycles was also observed in the reaction. A reaction mechanism involving a difluorocarbene intermediate, along with a subsequent formation of a -CF3 anion was proposed.
Lewis basicity modulation of N-heterocycles: A key for successful cross-metathesis
Lafaye, Kevin,Nicolas, Lionel,Gurinot, Amandine,Reymond, Sbastien,Cossy, Janine
supporting information, p. 4972 - 4975 (2015/01/08)
Cross-metathesis involving N-heteroaromatic olefinic derivatives is disclosed. The introduction of an appropriate substituent on the heteroaromatic ring decreases the Lewis basicity of the nitrogen atom, thus preventing the deactivation of the ruthenium-centered catalyst. The reaction is quite general in terms of both N-heterocycles and olefinic partners.
Novel phenyl-substituted imidazolidines, process for preparation thereof, medicaments comprising said compounds and use thereof
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Page/Page column 39, (2011/08/04)
The invention relates to compounds of formula (I) wherein the groups have stated meanings, and to their physiologically compatible salts. Said compounds are suitable, for example, as anti-obesity drugs and for treating cardiometabolic syndrome.
TRPA1 ANTAGONISTS
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Page/Page column 31-32, (2009/09/04)
Compounds of formula (I), wherein R1, R2, R3, and Y are defined in the description are TRPA1 antagonists. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.
PIPERIDINES AND RELATED COMPOUNDS FOR THE TREATMENT OF DEMENTIA
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Page/Page column 14, (2009/10/01)
Compounds of formula I: modulate the action of gamma secretase, and hence find use in treatment of Alzheimer's disease and related conditions.
N-PHENYL HYDRAZIDES AS MODULATORS OF THE GHRELIN RECEPTOR
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Page/Page column 182, (2009/01/24)
The present invention relates to novel compounds of formula (I) or a pharmaceutically acceptable salt or solvate thereof, wherein: each R1 is independently selected from the group consisting of Cl, Br, CH3 and CF3; X is carbon or nitrogen; R1a is H or a straight C1-3 alkyl group; R2a is H or a methyl group R2 is selected from the group consisting of C1-3alkyl, H and -(CH2)n-, wherein n is 3 or 4 and the terminal carbon of the chain is bonded to the carbon atom adjacent to the nitrogen bearing the R2 group, such that a fused 6,5 or 6,6-bicyclic ring is formed. Y is selected from the group consisting of: phenyl which may be unsubstituted or substituted by one or more substituents independently selected from the group consisting of C1-3alkyl, C1-3alkoxy, halogen, C1-3alkyl substituted by 1 to 7 fluoro atoms and C1-3alkoxy substituted by 1 to 7 fluoro atoms; pyridyl which may be unsubstituted or substituted by one or more substituents independently selected from the group consisting of C1-3alkyl, OCH3, CF3, CN, and halogen; naphthyl which may be unsubstituted or substituted by one or more substituents independently selected from the group consisting of F and OCH3; pyrimidinyl; imidazo[1,2-a]pyridine-6-yl; benzothiophen-2-yl; benzothiophen-5-yl; benzofuran-2-yl; dibenzo[b,d]furan-3-yl; dibenzo[b,d]thiophen-2-yl; dibenzo[b,d]thiophen-4-yl; 1,3- benzodioxol-5-yl; 2,3-dihydro-1,4-benzodioxin-5-yl; 2,3-dihydro-1,4-benzodioxin-6-yl; 2,3- dihydro-1-benzofuran-4-yl; 2,2-difluoro-1,3-benzodiox-4-yl; pyridazinyl; imidazolyl; oxazolyl; pyrazolyl; thiazolyl; and triazolyl; with the proviso that when Y is 2,3-dihydro-1,4-benzodioxin-6-yl, R1 is not Cl; processes for their preparation, intermediates useble in these processes, pharmaceutical compositions containing them and their use in therapy, for example as modulators of of the growth hormone secretagogue receptor (also referred to as the ghrelin receptor or GHSR1a receptor) and/or for the treatment and/or prophylaxis of a disorder mediated by the ghrelin receptor.
