Tag: M.W:100-200

Reference of 1945-84-2, 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. 1945-84-2, name is 2-Ethynylpyridine, molecular formula is C7H5N, 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.

General procedure: 3-Amino-2-bromopyridine (1a) (87 mg, 0.5 mmol) or2-bromoaniline (1b) (172 mg, 1.00 mmol), Pd(PPh3)2Cl2(9.0 mg, 13 mmol or 17.5 mg, 25.0 mmol), and(1-Ad)2PBn·HBr (12 mg, 25 mmol or 23.6 mg, 50.0 mmol)were placed into a dry screw-cap Schlenk tube with amagnetic stirring bar, and the vessel was evacuated. Afterflushing the vessel with nitrogen, dry DMSO (1.0 or 1.5 ml),the corresponding alkyne 2a-j (0.6 mmol or 1.2 mmol),and DBU (225 mg, 1.50 mmol or 457 mg, 3.00 mmol)were added. The reaction mixture was stirred at 100Cunder nitrogen for 1 h until the bromide was completelyconsumed (monitored by TLC). After cooling to roomtemperature, KOt-Bu (253 mg, 2.25 mmol or 281 mg,2.50 mmol) and DMSO (0.50 or 1.00 ml) were added to thereaction mixture, and the mixture was stirred at 100Cunder nitrogen for 0.25 h. After cooling to roomtemperature, deionized water or brine (20 ml) was added tothe mixture. The aqueous layer was extracted several timeswith EtOAc or CH2Cl2. The combined organic phases weredried over anhydrous Na2SO4 and after filtration, thesolvents were removed under reduced pressure. The residuewas purified by flash chromatography on silica gel to givethe analytically pure products 3a-j

According to the analysis of related databases, 1945-84-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lessing, Timo; Mueller, Thomas J. J.; Chemistry of Heterocyclic Compounds; vol. 54; 3; (2018); p. 334 – 338; Khim. Geterotsikl. Soedin.; vol. 54; 3; (2018); p. 334 – 338,5;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5632-81-5, 2-Chloropyridine-3,5-diamine, 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, 5632-81-5, blongs to pyridine-derivatives compound. category: pyridine-derivatives

REFERENCE EXAMPLE 18 Synthesis of ethyl 3-[(5-amino-6-chloropyridin-3-yl)amino]-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate To 1.4 g of ethyl 3-chloro-2,4,5-trifluorobenzoyl-acetate were added 1.5 g of acetic anhydride and 1.5 g of triethyl orthoformate, and the mixture was heated under reflux for 2 hours. The solvent was distilled off, and toluene was added to the residue for azeotropic distillation. 3 ml of chloroform was added to the half of the residue, and a solution of 360 mg of 3,5-diamino-2-chloropyridine in 3 ml ethanol was added dropwise to the mixture at room temperature and the mixture was stirred at room temperature for 30 minutes. The solvent was distilled off, and the residue was purified by column chromatography to obtain 200 mg of the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5632-81-5, its application will become more common.

Reference:
Patent; Wakunaga Pharmaceuticals Co., Ltd.; US5998436; (1999); A;,
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.882033-66-1, name is 4-Chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H4ClFN2, molecular weight is 170.5715, as common compound, the synthetic route is as follows.COA of Formula: C7H4ClFN2

Example 224A mixture of 4-chloro-5-fluoro-lH-pyrrolo [2, 3-b] pyridine (30 mg) , 3-piperidinecarboxamide (45 mg) and N,N-diisopropylethylamine (30 muL) inDMI(0.4mL) was heated in the microwave reactor (2000C, 2 hours) . The reaction mixture was allowed to cool to ambient temperature and diluted with EtOAc (10 mL) and half-saturated aqueous sodium hydrogencarbonate (10 mL) . The aqueous phase was extracted with EtOAc(2x 10 mL) and combined organic layers were washed with brine (20 mL) , dried over MgSO4, and concentrated. Purification of the crude product by preparative silica gel thin-layer chromatography (EtOAc) gave 1- (5-fluoro-lH-pyrrolo [2, 3-b]pyridin-4-yl) -3- EPO piperidinecarboxamide (5 mgj as a pale brown solid.1H-NMR(DMSO-d) delta : 11.5 (IH, s) , 7.96 (lH,d, J=5.7Hz) , 7.38 (IH, s) , 7.33 (1H,d, J=3.0Hz) , 6.87 (IH, s), 6.49 (IH, d, J=3.0Hz) , 3.82-3.70 (2H,m) ,3.21-3.06 (2H,m), 2.52-2.44 (IH,m) , 1.94-1.52 (4H,m) . ? MS(ESI) :m/z 263(M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,882033-66-1, 4-Chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/7919; (2007); A2;,
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. 136818-50-3, name is 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, the common compound, a new synthetic route is introduced below. name: 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid

To the stirred solution of lH-pyrrolo[2,3-b]pyridine-2-carboxylic acid (5, 2.5 g, 15.4 mmol) and Nu,Omicron-dimethylhydroxylamine hydrochloride (6, 1.8 g, 18.5 mmol in DCM (50 mL), was added triethylamine (10.6 mL, 77.1 mmol), HOBt (3.54 g, 23.14 mmol) followed by EDC.HC1 (4.42 g, 23.18 mmol) at 0C and the reaction mixture was stirred at room temperature for 16h. The reaction mixture was cooled to room temperature, filtered through celite and evaporated the filtrate. To the crude, added water (10 mL) and compound was extracted with DCM (30mL). Organic layer was dried over sodium sulfate and evaporated to get crude product. The crude residue was purified by gradient column chromatography using silica gel and eluent 2-4% MeOH in DCM to afford the product as off white solid. (Yield: 82%, 2.6 g). MS (ESI): mass calcd. for CioHnN302, 205.09; m/z found, 206.1 (M+H)+.

The synthetic route of 136818-50-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JUBILANT BIOSYS LIMITED; HALLUR, Gurulingappa; DURAISWAMY, Athisayamani Jeyaraj; PURRA, Buchi Reddy; RAO, N.V.S.K.; RAJAGOPAL, Sridharan; (247 pag.)WO2019/58393; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1215387-58-8, 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.1215387-58-8, name is 5-Bromo-1H-pyrrolo[2,3-c]pyridine, molecular formula is C7H5BrN2, molecular weight is 197.03, as common compound, the synthetic route is as follows.

To a stirred solution of 5-bromo-1H-pyrrolo[2,3-c]pyiidine (2.5 g, 12.75 mmol) in DMF (20 mL), 60% NaH (0.57 g, 15.30 mmol) was slowly added portionwise at 0 C. The resulting suspension was stirred at RT for 1h. The reaction mixture was cooled to 0 C and 2-(chloromethoxy)ethyl)trimethylsilane (2.55 g, 15.30 mmol) was added. The reaction mixture was allowed to stir at RT for 2h. The reaction mixture was quenched with water (70 mL), extracted with EtOAc (2 x 100 mL) and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude compound was purified by flash column chromatography and eluted with 15% EtOAc/pet ether to afford the title compound (2.7 g, 66%) as a liquid compound. LC-MS (method 1): R, = 2.73 min; m/z = 329.41 (M+H*+2).

Statistics shows that 1215387-58-8 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-1H-pyrrolo[2,3-c]pyridine.

Reference:
Patent; ORYZON GENOMICS, S.A.; SALAS SOLANA, Jorge; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; (195 pag.)WO2018/149986; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13534-97-9, 6-Bromopyridin-3-amine, 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, SDS of cas: 13534-97-9, blongs to pyridine-derivatives compound. SDS of cas: 13534-97-9

To a solution of 6-bromopyridin-3-amine (500 mg, 2.89 mmol) in CH3CN:DMF (3:2 mL) was added CuI (219 mg, 1.15 mmol) and triethylamine (2 mL, 14.4 mmol) and the solution was purged with argon for 15 min. Ethynyltrimethylsilane (1.2 mL, 8.67 mmol) and tetrakis(triphenyl phosphine)Pd(0) (100 mg, 0.086 mmol) were added and the solution was purged for another 30 min. The reaction mixture was heated to 45C for 2.5 h. Then, the reaction mixture was diluted with ethyl acetate (100 mL) and washed with saturated NaHCO3 solution (50 mL). The aqueous layer was re-extracted with ethyl acetate (3 X 50 mL). The combined organic layer was washed with water (2 X 50 mL), followed by brine and dried over sodium sulphate and concentrated in vacuo to afford 6-((trimethylsilyl)ethynyl)pyridin-3-amine 5 (776mg, 70percent).1H NMR (400 MHz, CDCl3) delta 8.04 (s, 1H), 7.25 (d, J=7.8 Hz, 1H), 6.91(d, J=7.8 Hz, 1H), 3.85 (br s, 2H), 0.24 (s, 9H). ES-MS m/z 191.00 (M+H)+.

The synthetic route of 13534-97-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse Marie, Josee; (134 pag.)WO2016/73889; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 628691-85-0, Adding some certain compound to certain chemical reactions, such as: 628691-85-0, name is 2,4-Dichloro-3-fluoropyridine,molecular formula is C5H2Cl2FN, 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 628691-85-0.

Step 2: Synthesis of 2-chloro-3-fluoro-4-(4-aminophenoxy)pyridine A solution of 4-aminophenol (24.8 g, 227 mmol) in anhydrous dimethyl sulfoxide (210 mL) was bubbled with nitrogen gas for 10 minutes, and potassium tert-butoxide (26.80 g, 238.8 mmol) was then added to get a reaction mixture. The reaction mixture was stirred at room temperature for 30 minutes, and then 2-chloro-3-fluoro-4-chloropyridine (37.68 g, 227 mmol) was added. The reaction mixture was stirred at room temperature for 5 h, and then diluted with water (1000 mL) and extracted with ethyl acetate (500 mL*3). The organic phases were combined. The combined organic phases were washed with saline solution (500 mL*2), dried with anhydrous sodium sulfate, filtrated, and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=5:1, v/v) to get product as light yellow solid (15.0 g, yield: 28%). 1H NMR (300 MHz, DMSO-d6): delta 5.22 (br s, 2H), 6.62 (d, J=9.0 Hz, 2H), 6.75 (t, J=5.7 Hz, 1H), 6.92 (d, J=9.0 Hz, 2H), 8.05 (d, J=5.7 Hz, 1H) MS (ESI+): m/z 239.1 [M+H]+

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 628691-85-0, 2,4-Dichloro-3-fluoropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PEKING UNIVERSITY FOUNDER GROUP CO., LTD.; PKUCARE PHARMACEUTICAL R&D CENTER; PKU HEALTHCARE INDUSTRY GROUP CO., LTD.; YI, Chongqin; XU, Heng; TAO, Jing; LIN, Songwen; HAN, Fangbin; (42 pag.)US2017/29404; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13362-78-2 , The common heterocyclic compound, 13362-78-2, name is (E)-1,2-Di(pyridin-4-yl)ethene, molecular formula is C12H10N2, 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.

A mixture of (E)-1,2-di(4-pyridyl)ethylene (91 mg, 0.5 mmol) and sodium 2-bromoethanesulfonate (317 mg, 1.5 mmol) (Aldrich) in abs. EtOH (3 mL) was refluxed with stirring for 50 h. The insoluble substance was filtered, washed with benzene, MeOH, and acetone, and re-crystallized from water-EtOH (2.8:1 (v/v), 2.7 mL) to yield 128 mg (64percent) of (E)-3a as a pinkish powder.

The synthetic route of 13362-78-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vedernikov, Artem I.; Lobova, Natalia A.; Kuz’mina, Lyudmila G.; Howard, Judith A.K.; Strelenko, Yuri A.; Alfimov, Michael V.; Gromov, Sergey P.; Journal of Molecular Structure; vol. 989; 1-3; (2011); p. 114 – 121;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1658-42-0, Adding some certain compound to certain chemical reactions, such as: 1658-42-0, name is Methyl 2-(pyridin-2-yl)acetate,molecular formula is C8H9NO2, 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 1658-42-0.

To a stirred solution of methyl 2-(pyridin-2-yl)acetate (190 g, 1.260 mol) in 1,4- dioxane (1.9 L) was added Triton-B (Benzyl Trimethyl ammonium hydroxide) (46 mL, 0.252 mol) at room temperature and stirred for 10 min. Acrylonitrile (49.7 mL, 0.760 mol) was dissolved in 1,4-dioxane (0.9 L) and was added drop wise over period of 30 minutes. The resulting reaction mixture was stirred for 16 hr at room temperature. The reaction progress was monitored by TLC. After completion of the reaction (TLC), the reaction mixture was concentrated under reduced pressure to afford the crude title compound. Purification by column chromatography was by using (100-200 silica gels) using 15 percent ethyl acetate and pet. ether as the eluent afforded pure compound.

According to the analysis of related databases, 1658-42-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MANDAL, Mihir; TANG, Haifeng; XIAO, Li; SU, Jing; LI, Guoqing; YANG, Shu-Wei; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; HICKS, Jacqueline; LOMBARDO, Matthew; CHU, Hong; HAGMANN, William; PASTERNAK, Alex; GU, Xin; JIANG, Jinlong; DONG, Shuzhi; DING, Fa-Xiang; LONDON, Clare; BISWAS, Dipshikha; YOUNG, Katherine; HUNTER, David, N.; ZHAO, Zhiqiang; YANG, Dexi; WO2015/112441; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1206979-33-0, 6-Chloro-1H-pyrazolo[4,3-c]pyridine, 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, 1206979-33-0, blongs to pyridine-derivatives compound. category: pyridine-derivatives

At r.t. to a suspension of 6-chloro-1H-pyrazolo[4,3-c]pyridine (0.5 g, 3 mmol) (Frontier Cat. No. Z13659) in methylene chloride (3 mL) and THF (1 mL) was added methanesulfonic acid (42 muL, 0.65 mmol), followed by dihydropyran (0.89 mL, 9.8 mmol). The mixture was stirred at r.t. for 2 h., and then at 50 C. overnight. After cooling the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.8 g). LCMS (M+H)+=238.0; LCMS (M-84+H)+=154.0/156.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1206979-33-0, its application will become more common.

Reference:
Patent; Incyte Corporation; Zhuo, Jincong; Xu, Meizhong; Qian, Ding-Quan; US2014/171405; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem