Pyridine-derivatives

Application of 28733-43-9, Adding some certain compound to certain chemical reactions, such as: 28733-43-9, name is 5-Bromonicotinamide,molecular formula is C6H5BrN2O, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 28733-43-9.

To a solution of NaOH (22.9 g, 572 mmol) in water (245 mL) at 0-5 C. (ice salt bath) was added bromine (9.44 mL, 184 mmol) maintaining the temperature at 0-5 C., to produce a sodium hypobromite solution. To this NaOBr-sol. was added commercially available 3-bromonicotinamide (30.15 g, 150 mmol) all at once with vigorous stirring. After being stirred for 15 min, the solution is clear and mixture was heated to 70-75 C. for 45 min. Cooled to 23 C., saturated with solid NaCl, extracted with TBME/THF (3×300 mL), dried over Na2SO4. Removal of the solvent in vacuum gave a dark brown oil which was purified by silica gel column chromatography with heptane/EtOAc 1:1?2:3 to give the title compound as a brown solid (16.036 g, 62%). MS (ISP) 173.1 [(M+H)+], 175.2 [(M+2+H)+].

According to the analysis of related databases, 28733-43-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; McArthur, Silvia Gatti; Goetschi, Erwin; Palmer, Wylie Solang; Wichmann, Juergen; Woltering, Thomas Johannes; US2006/217387; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1122-72-1, name is 6-Methyl-2-pyridinecarboxaldehyde, molecular formula is C7H7NO, molecular weight is 121.14, as common compound, the synthetic route is as follows.SDS of cas: 1122-72-1

(i) 6-Methyl-2-hydroxymethylpyridine 6-Methylpyridine-2-carboxaldehyde (0.44 mmole) in 50 ml methanol was reduced with 20.6 mmole sodium borohydride at 0-5 C. After reduction was complete, the mixture was neutralized (pH 7.5) with 2N sulfuric acid, filtered, the filtrate concentrated band partitioned between chloroform and water. Evaporation of solvent from the organic layer gave 3.32 g of red-black oil which was used in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1122-72-1, 6-Methyl-2-pyridinecarboxaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; EP150984; (1991); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 183208-34-6 ,Some common heterocyclic compound, 183208-34-6, molecular formula is C7H5BrN2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Example 44A tert-butyl (1S,2Z)-2-(5-bromo-2-oxo-1,2-dihydro-3H-pyrrolo[2,3-b]pyridin-3-ylidene)-1-(1H-indol-3-ylmethyl)ethylcarbamate A mixture of 5-bromo-7-aza-oxindole (D. Mazeas, et al., Heterocycles 1999, 50, 1065.) (213 mg, 1.0 mmol), L-BOC-tryptophanal (290 mg, 1.0 mmol) and piperidine (40 muL) in ethanol was refluxed for 2.5 hours and concentrated. The residue was triturated with dichloromethane (1 mL) and hexane (6 mL) and dried to provide the desired product (512 mg). MS (DCI/NH3) m/e 483, 485 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,183208-34-6, its application will become more common.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 96428-50-1 , The common heterocyclic compound, 96428-50-1, name is Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate, molecular formula is C18H18N2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Example 24A Ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate 31.45 g (101.3 mmol) of ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate from Example 23A were dissolved in 2 l of ethyl acetate, 3.15 g of 10% Pd/carbon were added and the mixture was stirred at RT and standard hydrogen pressure for 5 h. The mixture was filtered through kieselguhr, the filter cake was washed well with ethyl acetate/methanol and the filtrate was concentrated to dryness. This gave 21.94 g of the target compound (98% of theory, purity 99%). LC-MS (Method 1): Rt=0.61 min MS (ESpos): m/z=221 (M+H)+ 1H-NMR (400 MHz, DMSO-d6): delta=1.36 (t, 3H), 2.60 (s, 3H), 4.36 (q, 2H), 6.78 (d, 1H), 6.98 (t, 1H), 8.73 (d, 1H), 10.60 (br s, 1H).

The synthetic route of 96428-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; VAKALOPOULOS, Alexandros; VALOT, Gaelle; LINDNER, Niels; FOLLMANN, Markus; WUNDER, Frank; STASCH, Johannes-Peter; MARQUARDT, Tobias; REDLICH, Gorden; DIETZ, Lisa; Ll, Volkhart Min-Jian; (94 pag.)US2017/57954; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59290-81-2, 2-Methyl-5-nitro-3-pyridinecarboxylic acid, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 59290-81-2, blongs to pyridine-derivatives compound. Safety of 2-Methyl-5-nitro-3-pyridinecarboxylic acid

Step 1: Synthesis ofZ-1aED-1 a (15.6 g, 85.7 mmol) is placed in ie/f.-BuOH (300 mL), combined with DPPA (27 mL, 125 mmol) and NMM (12 mL, 108 mmol) and refluxed for 5 h. After cooling, saturated sodium chloride solution is added and the mixture is extracted several times with EA. The combined organic phases are washed with saturated sodium chloride solution, dried on MgS04, filtered and evaporated down using the rotary evaporator. The residue is taken up in water and freeze-dried. The resulting Z-1 a (HPLC-MS: tRet. = 1 .73 min; MS (M+H)+ = 254) is used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59290-81-2, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ETTMAYER, Peter; STEURER, Steffen; WO2011/117382; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 135124-71-9 ,Some common heterocyclic compound, 135124-71-9, molecular formula is C7H6N2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

d) 5-Cyano-pyridine-3-carbaldehyde A black suspension of (5-cyano-pyridin-3-yl)-methanol (0.070 g, 0.52 mmol), anhydrous CH2Cl2 (1.04 mL) and manganese oxide (0.181 g, 2.09 mmol) was heated to reflux and monitored by TLC. After 8 h, the reaction mixture was cooled to room temperature and additional manganese oxide (0.095 g, 1.1 mmol) was added to the reaction flask. The reaction mixture was then heated to reflux. After 18 h, the reaction was still not complete by TLC and additional manganese oxide (0.097 g, 1.1 mmol) was added to the reaction flask. After heating at 60 C. for 72 h, the reaction mixture was cooled to room temperature, diluted with EtOAc (50 mL), passed through celite and washed with additional EtOAc (50 mL). The organic filtrate was dried over MgSO4, filtered through sintered glass and concentrated to yield 0.064 g (93%) of a white solid. It was purified by column chromatography (elution with EtOAC:hexanes, 1:3) and yielded 0.038 g (55%) of the title compound as a white solid. 1H NMR (CDCl3): 10.17 (s, 1H), 9.28 (d, J=1.9 Hz, 1H), 9.11 (d, J=2.2 Hz, 1H), 8.45 (dd, J=2.2, 1.9 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135124-71-9, its application will become more common.

Reference:
Patent; Cytovia, Inc.; US2006/104998; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine, the common compound, a new synthetic route is introduced below. Formula: C6H5BrClN

Example 1; Synthesis of 3-(2-amino-6-quinazolinyl)-1 -(3-chlorophenyl)-4-methyl-2(1 H)- pyridinone; Step 1 : 2-(4-methoxybenzyloxy)-3-bromo-4-methyl; Pyridine To a mixture of 60% NaH in mineral oil (0.290 g, 7.27 mmol) in THF (15 ml_) at RT in a resealable pressure vessel was added (4-methoxyphenyl)methanol (0.906 ml, 7.27 mmol). After 5 minutes, 3-bromo-2-chloro-4-picoline (1.00 g, 4.84 mmol) was added and the mixture was heated to 75 0C. After 1 hr, water was added and the mixture was diluted with EtOAc. After washing with water and brine, the organic fraction was dried with sodium sulfate and purified by silica gel chromatography using 0-30% EtOAalphahexanes to afford 2-(4-methoxybenzyloxy)- 3-bromo-4-methylpyridine as a colorless oil. M+H+ = 308.0.

The synthetic route of 55404-31-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2008/11109; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 189230-41-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 189230-41-9 as follows.

[0355] Reference AD [0356] Synthesis of 5-chloro-N-cyclopropyl-3-(4-(2-fluoro-4-methoxyphenoxy)piperidin-l- yl)pyrido[3,4-b]pyrazin-2-amine [0358] [0359] Step 1 : 5-bromopyrido[3,4-b]pyrazine-2,3(lH,4H)-dione [0360] A solution of l,2-di(lH-imidazol-l-yl)ethane-l,2-dione (1.456 g, 7.66 mmol) and 2- bromopyridine-3,4-diamine (1.2 g, 6.38 mmol) in DMF (21.27 ml) was stirred at RT overnight. The precipitate was filtered and washed with anhydrous THF to give the title compound as a grey solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189230-41-9, its application will become more common.

Reference:
Patent; ENVOY THERAPEUTICS, INC.; HITCHCOCK, Stephen; MONENSCHEIN, Holger; REICHARD, Holly; SUN, Huikai; KIKUCHI, Shota; MACKLIN, Todd; HOPKINS, Maria; WO2014/28479; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 122306-01-8, name is (6-Bromopyridin-3-yl)methanol, molecular formula is C6H6BrNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. COA of Formula: C6H6BrNO

To a mechanically-stirred solution of 78.12 g of thionyl chloride in 450 mL of acetonitrile at 15 C. was added a solution of 160.75 g of 3-hydroxymethyl-6-bromopyridine in 446 mL of acetonitrile over 30 minutes. The temperature rose to 22 C. during the addition, and the reaction mixture was stirred for 15 minutes at room temperature. The mixture was cooled in an ice bath, and a solution of 70 g of NaOH in 1.4 L of water was added at such a rate that the temperature did not exceed 15 C. 603 mL of toluene was added to the mixture and stirred rapidly. The layers were separated. The aqueous phase was reextracted with toluene. The combined organic phase was concentrated in vacuo to give 181.61 g of 3-chloromethyl-6-bromopyridine.

With the rapid development of chemical substances, we look forward to future research findings about 122306-01-8.

Reference:
Patent; G. D. Searle & Co.; US5420270; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 130473-26-6, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 130473-26-6, name is 1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid. The solution is cooled to in an ice bath, 30% aqueous hydrogen peroxide (722 muL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5 C. The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid. The formate salt is added to 7 mL water, 3 mL 2N NaOH is added, and the pH is adjusted to 3 with 5% aqueous HCl. The precipitate is collected and is dried to afford 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (C176) (67% yield). HRMS (FAB) calculated for C8H6N2O2+H: 163.0508, found 163.0507 (M+H)+.

According to the analysis of related databases, 130473-26-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem