4-methoxyphenyl pyridine

Electrochemical preparation of an arylzinc bromide and its coupling with 2-chloropyridine synthesis of 2-(4-methoxyphenyl)pyridine... 

Purify the crude product by chromatography using pentane ether (4 1). Pure 2(4-methoxyphenyl)pyridine is obtained as a white solid (764 mg, 55%) and characterized by 1H and 13C NMR. 

While oxidation of the benzenediboronic acids with alkaline hydrogen peroxide affords the corresponding 1,3- and 1,4-dihydroxybenzenes (70-72%), the pyridinediboronic acids lead via a double Pd(0) catalyzed Suzuki reaction with 4-iodoanisole to 2,5- and 2,6-Z /s-(4-methoxyphenyl)pyridines (Sch. 36) [107]. 

B. Ethyl l-( p-methoxyphenyl I-2-oxoayotohexaneaar hoxylate. A 250 mL, one-necked, round-bottomed flask, equipped with a magnetic stirring bar, is charged with 22.2 g (45 mmol) of p-methoxyphenyl 1 ead triacetate, 10.8 g (135 mmol) of pyridine (Note 8), and 70 mL of chloroform (Note 9). To this solution 1s added 7.0 g (41 mmol) of ethyl 2-oxocyclohexanecarboxylate (Note 10), a calcium chloride drying tube Is put 1n place, and the mixture is stirred at 40°C (Note 11). 

Reaction of 2-cyano-3-(4-methoxyphenyl)acroyl chloride and 2-amino-pyridine in boiling benzene in the presence of NEt3 for 5 h gave a 2 1 mixture of 3-cyano-4-(4-methoxyphenyl)-3,4-dihydro-2//-pyrido[l, 2-n]pyr-imidin-2-one and 2- [2-cyano-3-(4-methoxyphenyl)acroyl]amino pyridine (01SUL151). 

Lopez-Rodriguez ML et al. (1996) Synthesis and structure-activity relationships of a new model of arylpiperazines. 1. 2-[[4-(o-Methoxyphenyl)piperazin-l-yl]methyl]-1, 3-dioxoperhydroimidazo[l,5-alpha]pyridine a selective 5-HTlA receptor agonist. J Med Chem 39(22) 4439-4450... 

Chelating pyrazole ligands are also known. The pseudo-octahedrally coordinated zinc complex ZnL2(pyridine)2 was formed where L = 5-(4-methoxyphenyl)pyrazole-3-carboxylate.850... 

Light-induced excited spin state trapping Light-induced thermal hysteresis 4- (p-Methoxyphenyl)-1,2,4-triazole 4- (p-Tolyl) -1,2,4-triazole Pyridine... 

DCM (anhydrous), DMSO (anhydrous), triethylamine (99 + %), sulfur trioxide-pyridine complex, DMA (anhydrous), potassium tert-butoxide (95%), DCE (anhydrous), 2-(4-methoxyphenyl)ethylamine (98 + %), sodium triacetoxy-borohydride (95%), A/A-diisopropylethylamine (99%), p-toluenesulfonyl chloride (99 + %), and trifluoroacetic acid (99 + %) were obtained from Aldrich Chemical Company, Inc. 4-Hydroxy-2-methoxybenzaldehyde (>98%) was obtained from Fluka Chemie, AG. 

Tertiary benzylic nitriles are useful synthetic intermediates, and have been used for the preparation of amidines, lactones, primary amines, pyridines, aldehydes, carboxylic acids, and esters. The general synthetic pathway to this class of compounds relies on the displacement of an activated benzylic alcohol or benzylic halide with a cyanide source followed by double alkylation under basic conditions. For instance, 2-(2-methoxyphenyl)-2-methylpropionitrile has been prepared by methylation of (2-methoxyphenyl)acetonitrile using sodium amide and iodomethane. In the course of the preparation of a drug candidate, the submitters discovered that the nucleophilic aromatic substitution of aryl fluorides with the anion of a secondary nitrile is an effective method for the preparation of these compounds. The reaction was studied using isobutyronitrile and 2-fluoroanisole. The submitters first showed that KHMDS was the superior base for the process when carried out in either THF or toluene (Table I). For example, they found that the preparation of 2-(2-methoxyphenyl)-2-methylpropionitrile could be accomplished h... 

Dichloro-5-methoxyphenyl)amino]thieno[3,2- ]pyridine-6-carbonitriles substituted with heteroaryl groups at position C-2, 160, have been found to inhibit Src kinase activity. The highest activity in Src and cell assays has been found with a 2,5-furan or 2,5-pyridine substituent at C-2 <2005BML4681, 2005JME3891>. 

Compound 142 was prepared by reacting 141 with chloroacetic acid under basic conditions which were accompanied by the loss of CO2. Acetylation and benzoylation of 141 with boiling AC2O or benzoyl chloride in pyridine yielded the corresponding 3-acetyl(benzoyl) derivatives 143 and 144, respectively <1994H(38)57>. Alkylation of 6-benzyl-5,6,7,8-tetrahydropyrido[4,3-tf pyrimidin-4(3//)-one 145 with l-(2-methoxyphenyl)-4-(2-chloroethyl)piper-azine afforded the 3-substituted derivative 146 <2000DEP19900544>. 

Hydrolysis of 5-(4-methoxyphenyl)-7-(4-tolyl)-2-methyl-3-aminopyrido[2,3-aqueous pyridine was accompanied by ring fission to give the pyridine derivative 200 <1994H(38)57>. 

This procedure illustrates the best way to prepare aryl isocyanides. It is quite general, having been used by Ugi and Meyr e to make the following isocyanides from the corresponding form-amides phenyl (56%), />-tolyl (66%), 2,6-dimethylphenyl (88%), mesityl (80%), o-chlorophenyl (43%), -chlorophenyl (54%), 2-chloro-6-methylphenyl (87%), -methoxyphenyl (64%), p-di-ethylaminophenyl (75%), -nitrophenyl (41%), and 2-naphthyl (50%). Aliphatic isonitriles are generally best prepared by a simpler procedure involving the action of phosphorus oxychloride on an N-alkylformamide in the presence of pyridine.7... 

D(p-F)PPAP (lOe) 6-bis(4-fluorophenyl)-phosphino-2-(pivaloylamino)pyridine, 3-D(p-MeO) PICon (11b) 3-bis(4-methoxyphenyl)phosphinoisoquinolone, 3-D(p-F)PICon (lid) 3-bis(4-fluorophenyi)phosphinoisoquinolone. 

Tetranuclear aromatic diamines were prepared on the basis of bis-phenols derived from 1,1,1-trichloro-2,2-di-(p-methoxyphenyl)-ethane under the action of pyridine hydrochloride [26, 27]. Interaction of the bis-phenols with two-fold molar amounts of p-nitrochlorobenzene led to the formation of 4,4 -bis(/ -nitrophenoxy [-arylenes, which were reduced to the corresponding 4,4 -bis(/ -aminophenoxy[-arylenes [28] (Scheme 2.11). Similar compounds containing two additional amino groups were prepared by the interaction of 3,3 -dinitro-4,4 -dichlorobenzophenone with two-fold molar amounts of potassium p-nitrophenolate [29] followed by reduction of the tetranitro compounds thus formed [29] (Scheme 2.12). 

The methoxy derivatives may be treated directly o-methoxyphenyl-acetone, heated with hydrobroniic acid in acetic acid, gives 2-methyl-benzofuran.326 o-Methoxylated phenylacetones are readily prepared by glycidic synthesis from o-methoxylated aromatic aldehydes the intermediate glycidic ester (127) can be directly converted by pyridine hydrochloride into a 2-alkylbenzofuran in 40-80% yield.105... 

An important extension of this method has made it possible to synthesize polycyclic benzofurans under the influence of various demethylating and dehydrating media.335 For such ring closures, pyridine hydrochloride is especially suitable thus coumestan has been synthesized from 4-hydroxy-3-(2-methoxyphenyl)coumarin.8 4,7-Di hydroxy-3-(2,4-dimethoxyphenyl)coumarin gives coumestol with aniline hydrochloride 336 other polymethoxycoumestans have been obtained with pyridine hydrochloride or with HBr (or HI) and acetic acid.337-339... 

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