Month: April 2022

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.89282-03-1, name is 3-Iodopyridin-4-ol, molecular formula is C5H4INO, molecular weight is 221, as common compound, the synthetic route is as follows.name: 3-Iodopyridin-4-ol

General procedure: In a pressure tube, a suspension of 5% Pd/C (5 mol%), 2-bromo-3-hydroxypyridine (0.5 mmol), LiCl (0.5 mmol),cesium carbonate (1 mmol), and terminal alkyne (1.0 mmol)in DMF (3 mL) was stirred for designated period at 150 C.The reaction mixture was filtered, and neutralized with saturatedNH4Cl solution, followed by extraction with ethyl acetate.The crude product was purified by columnchromatography with the use of hexane and ethyl acetate aseluents.The following compounds were prepared with abovedescribed general procedure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89282-03-1, 3-Iodopyridin-4-ol, and friends who are interested can also refer to it.

Reference:
Article; Park, Hee Jung; Kim, Ji-Eun; Yum, Eul Kgun; Kim, Young Hoon; Han, And Chang-Woo; Bulletin of the Korean Chemical Society; vol. 36; 1; (2015); p. 211 – 218;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 60010-03-9, 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.60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine, molecular formula is C6H4Cl2N2O2, molecular weight is 207.01, as common compound, the synthetic route is as follows.

6-Chloro-2-((f?)-3-fluoro-pyrrolidin-1 -yl)-4-methyl-3-nitro-pyhdine (Intermediate compound)To a solution of 2,6-dichloro-4-methyl-3-nitropyhdine (6.5g; 31.4 mmol) and TEA (1 Og; 3eq) in acetonitrile (200ml) was added (f?)-(-)-3-fluoropyrrolidine hydrochloride (4.75g; 1.2eq). The mixture was stirred for 4h at rt, after which the reaction mixture was quenched with sat NaHCOs(aq) (300ml), diluted with water and and EtOAc. The layers were separeted and the waterlayer was extracted with EtOAc (3x15OmL) untill no UV(254nm) active material was extracted). The com- bined organic layers were washed with brine and dried over Na2SO4(s). Filtration and in vacuo concentration resulted in a quantitative yield 8.36g of the title compound as a yellow/orange oil.

Statistics shows that 60010-03-9 is playing an increasingly important role. we look forward to future research findings about 2,6-Dichloro-4-methyl-3-nitropyridine.

Reference:
Patent; NEUROSEARCH A/S; BROWN, William, Dalby; JESSEN, Carsten; MATTSSON, Cecilia; SOTT, Richard; STRØBAeK, Dorte; WO2010/122064; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 824-51-1 , The common heterocyclic compound, 824-51-1, name is 6-Methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H8N2, 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.

To a solution of 6-methyl-1H-pyrrolo[2,3-b]pyri- dine (500 mg) in dichioroethane (6 mE) were added aluminum chloride (1.09 g) and acetyl chloride (0.40 mE), and then the mixture was stirred at room temperature for 1 .5 hours. The reaction solution was poured into aqueous saturated sodium hydrogen carbonate solution, and extracted with chloroform. The organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was triturated with isopropyl ether to give 1 -(6-methyl-1H-pyrrolo[2,3-b]pyri- din-3-yl)ethanone [REx(8-i)] (481 mg) as a yellow powder. APCI-MS mlz: 175 [M+H].

The synthetic route of 824-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Pharmaceuticals Holding CO., LTD.; MITSUBISHI TANABE PHARMA CORPORATION; Iijima, Toru; Takahashi, Yoichi; Hirai, Miki; Sugama, Hiroshi; Togashi, Yuko; Shen, Jingkang; Xia, Guangxin; Wan, Huixin; US2015/232459; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15862-50-7, 3-Bromo-2-methoxy-5-nitropyridine, 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, 15862-50-7, blongs to pyridine-derivatives compound. Formula: C6H5BrN2O3

2nd Step Pd(PPh3)4 (60 mg) and tributyl (1-ethoxyvinyl)tin were added to a DMAc (3 ml) solution containing 3-bromo-2-methoxy-5-nitropyridine (69 mg) obtained in the 1st step, followed by microwave irradiation (Initiator, 180 C., 10 minutes, 2.45 GHz, 0-240 W). Saturated sodium hydrogen carbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure and the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=9:1 to 3:7). A light yellow solid of 1-(2-methoxy-5-nitropyridin-3-yl)ethanone (72 mg) was thus obtained. MS (ESI m/z): 197 (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,15862-50-7, its application will become more common.

Reference:
Patent; FUJIFILM Corporation; FUJIWARA, Hideyasu; MIZUMOTO, Shinsuke; KUBO, Yohei; NAKATA, Hiyoku; HAGIWARA, Shinji; BABA, Yasutaka; TAMURA, Takashi; KUNIYOSHI, Hidenobu; MASHIKO, Tomoyuki; YAMAMOTO, Mari; US2014/309225; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 57883-25-7 ,Some common heterocyclic compound, 57883-25-7, molecular formula is C7H8BrNO, 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.

To a solution of 3-bromo-2-ethoxy-pyridine (350 mg, 1.7 mmol) in NMP (2 mL) was added Zn(CN)2 (244 mg, 2.1 mmol) and Pd(dppf)C12 (127 mg, 0.17 mmol). The mixture was degassed with N2 and heated at 140C under microwave irradiation for 1 hour. The mixture was cooled to roomtemperature and filtered through celite. The filtered cake was washed with ethyl acetate (30 mL). The filtrate was washed with water (20 mL x 2) and brine (20 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (0%20% ethyl acetate in petroleum ether) to give 2-ethoxynicotinonitrile.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57883-25-7, its application will become more common.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (278 pag.)WO2019/115567; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16727-47-2, 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.16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, molecular formula is C19H16BrNO2, molecular weight is 370.2398, as common compound, the synthetic route is as follows.

Step-1: Preparation of 2-(2,6-Bis-benzyloxy-pyridin-3-yl)-2,6-dihydro-4H-pyrrolo[3,4- c]pyrazole-5-carboxylic acid tert-butyl ester (26-2) (1327) (1328) Compound 26-2 was synthesized according to Scheme 26. Yield: 12%; LC MS: ES+ 499.3.

Statistics shows that 16727-47-2 is playing an increasingly important role. we look forward to future research findings about 2,6-Bis(benzyloxy)-3-bromopyridine.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; CHEN, Chi-li; DUPLESSIS, Martin; HE, Minsheng; LAZARSKI, Kiel; (980 pag.)WO2017/197051; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56946-65-7, 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]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, 56946-65-7, blongs to pyridine-derivatives compound. HPLC of Formula: C8H7Cl2N

To a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopenta[Z?]pyridine (0.152 g, 0.81 mmol) in dioxane (3 mL) was added 2-(tributylstannyl)oxazole (0.318 g, 0.89 mmol) and tetrakis(triphenylphosphine)palladium (0.046 g, 0.040 mmol). The mixture was purged with nitrogen and then heated to 110 C under sealed conditions for 16 h. After this time, the mixture was diluted with water and extracted with ethyl acetate. The organic layer were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.061 g, 34%) as a white solid. MW = 220.66. ]H NMR (CDC13, 500 MHz) delta 7.94 (s, 1H), 7.78 (s, 1H), 7.29 (s, 1H), 3.19 (t, / = 7.5 Hz, 2H), 3.06 (t, / = 7.5 Hz, 2H), 2.22 (quin, J = 7.5 Hz, 2H); APCI MS m/z 221 [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,56946-65-7, its application will become more common.

Reference:
Patent; TETRA DISCOVERY PARTNERS, LLC.; GURNEY, Mark, E.; HAGEN, Timothy, J.; MO, Xuesheng; VELLEKOOP, A.; ROMERO, Donna, L.; CAMPBELL, Robert, F.; WALKER, Joel, R.; ZHU, Lei; WO2014/66659; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 885588-17-0, Adding some certain compound to certain chemical reactions, such as: 885588-17-0, name is 5-Fluoro-2-methylisonicotinic acid,molecular formula is C7H6FNO2, 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 885588-17-0.

To a mixture of 5-fluoro-2-methylisonicotinic acid (200 mg) in dichloromethane (7 ml) und DMF (1 ml) was subsequently added at 22 C EDCI (198 mg), HOBT (158 mg) and triethylamine (163 mg) and stirring was continued for 15 min. l,3,3-Trimethyl-2-oxoindoline-6- carbohydrazide (165 mg) was added and stirring was continued for 18 h. The mixture was evaporated and the residue purified by flash chromatography (silica gel, gradient, 0% to 10% MeOH in dichloromethane) to give the title compound (186 mg, 62%) as yellow oil. MS (ESI, m/z): 371.1 [(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. 885588-17-0, 5-Fluoro-2-methylisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1221171-88-5 ,Some common heterocyclic compound, 1221171-88-5, molecular formula is C6H5F3N2O, 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.

The product of Example 158B (62 mg, 0.11 mmol) and (1509) bis(tetramethylene)fluoroformamidinium hexafluorophosphate (50 mg, 0.16 mmol, Alfa) were charged to a sealed tube, and a solvent mixture of dichloromethane (0.26 mL) and N,N- diisopropylethylamine (0.083 mL, 0.47 mmol) was added in one portion. The resulting mixture was stirred at ambient temperature for 30 minutes and 5-(trifluoromethoxy)pyridin-2-amine (22.5 mg, 0.13 mmol, Astatech) was added. The tube was sealed and stirred at 75 C for 18 hours. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The resulting residue was dissolved in N,N-dimethylformamide (3 mL), filtered through a glass microfiber frit and purified by preparative HPLC [YMC TriArt CI 8 Hybrid 5 mupiiota column, 50 x 100 mm, flow rate 70 mL/minute, 5-100% gradient of acetonitrile in buffer (0.025 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to give the title compound (12 mg, 0.023 mmol, 22% yield). JH NMR (400 MHz, DMSO-<) ppm 9.95 (s, 1H), 8.39 - 8.36 (m, 1H), 8.11 (dd, J = 9.2, 0.6 Hz, 1H), 7.83 (ddd, J = 9.2, 3.0, 1.0 Hz, 1H), 7.48 - 7.41 (m, 2H), 7.00 (dd, J = 11.4, 2.8 Hz, 1H), 6.78 (ddd, J = 9.0, 2.8, 1.2 Hz, 1H), 4.42 (s, 2H), 1.92 - 1.78 (m, 12H). MS (APCI+) m/z 516 (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,1221171-88-5, its application will become more common. Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 886365-46-4, Adding some certain compound to certain chemical reactions, such as: 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid,molecular formula is C7H6ClNO2, 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 886365-46-4.

To a solution of tert-butyl ((3aR,4R,8S)-4-(6-amino-3-fluoropyridin-2-yl)-4,7,7- trimethyl-8-oxido-3,3a,4,7-tetrahydro-2H-isothiazolo[l,5-a][l,4]thiazin-6-yl)carbamate (Int- 39BA, 150 mg, 0.35 mmol) in THF (20 mL) was added 5-chloro-3-methylpicolinic acid (92.4 mg, 0.53 mmol) followed by T3P (1.1 g, 1.75 mmol, 50% in ethyl acetate), and diisopropylethylamine (267 mg, 2.1 mmol). The reaction was stirred at 70 C for 4 h. After that, the reaction mixture was diluted with aqueous saturated sodium hydrogencarbonate solution (20 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give a crude product. The crude was purified by preparative TLC (silica gel, dichloromethane / ethyl acetate 1: 1, UV) to yield, after drying in vacuo, the title compound as a yellow solid (100 mg, 50% yield). MS (ES+) m/z 579.2 [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. 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem