Tag: M.W:200-300

Application of 85333-26-2, Adding some certain compound to certain chemical reactions, such as: 85333-26-2, name is 2-Amino-4-benzyloxypyridine,molecular formula is C12H12N2O, 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 85333-26-2.

A mixture of 2-amino-4-benzyloxypyridine (2.00 g, 9.49 mmol), copper (I) bromide (70 mg, 0.05 mmol), 1,10-phenanthroline monohydrate (95 mg, 0.05 mmol) and benzonitrile (25 mL) was heated in a 50-mL 3-necked flask to 130 C. During 23 h a gentle flow of (O2/N2 5:95) was bubbled through the reaction mixture (>99% conversion, HPLC method see below). The dark brown solution was then evaporated at 60 C./0.1 mbar to dryness and the dark brown residue dissolved in DCM (30 mL). The organic solution was washed with water (30 mL), dried over sodium sulphate, filtered and evaporated to yield an dark oil containing crude 7-benzyloxy-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine and residual benzonitrile. [0099] Charcoal treatment of the crude product with Norit SA II (0.90 g) in EtOAc (120 mL) at reflux, filtration and subsequent crystallization (via partial evaporation of EtOAc and addition of heptane) afforded 7-benzyloxy-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (1.78 g, 62%) as an off-white solid with >99.9% purity (HPLC area-%, HPLC method: Onyx monolithic C18 column, 100×4.6 mm; mobile phase, A: water/NCMe (95:5), B: NCMe; flow: 2.0 ml/min; gradient from 95/5 (A/B) to 15/85 (A/B) within 3 min, isocratic 15/85 (A/B) for 2.5 min. Retention time: 3.40 min (2-amino-4-benzyloxypyridine), 3.60 min 7-benzyloxy-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine)). [0100] EI-MS: m/z=302.13 (M+H)+.

According to the analysis of related databases, 85333-26-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HOFFMANN-LA ROCHE INC.; Bartels, Bjoern; Fantasia, Serena Maria; Flohr, Alexander; Puentener, Kurt; Wang, Shaoning; US2014/350259; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 70201-42-2, name is 3,5-Dibromoisonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. name: 3,5-Dibromoisonicotinaldehyde

Example 126a 3-Bromo-5-(1-oxo-6,7,8,9-tetrahydropyrazino[1,2-a]indol-2(1H)-yl)isonicotinaldehyde 126a A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1,4-dioxane (15 mL), 3,5-dibromoisonicotinaldehyde (604 mg, 2.28 mmol), 6,7,8,9-tetrahydropyrazino[1,2-a]indol-1(2H)-one (142 mg, 0.76 mmol) and cesium carbonate (485 mg, 1.5 mmol). CuI (143 mg, 0.76 mmol) and 4,7-dimethoxy-1,10-phenanthroline (127 mg, 0.52 mmol) were added, and the reaction mixture was heated at 100 C for 5 h. After this time, the reaction was cooled to room temperature. It was then filtered and the filtrate was concentrated under reduced pressure. The residue was purified on flash column eluting with EtOAC/PE (1:2) to afford 126a (100 mg, 35%) as a yellow solid. MS: [M+H]+ 372.

With the rapid development of chemical substances, we look forward to future research findings about 70201-42-2.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
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. 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid, the common compound, a new synthetic route is introduced below. Quality Control of 3-Chloro-5-(trifluoromethyl)picolinic acid

(1) Add 2 mmol) to a 25 ml three-necked flask3,5-Difluoro-5-(trifluoromethyl)picolinic acid8.0 mmol) pyridine and 5 ml acetonitrile, and the ice bath was cooled down to -5C. Then, 0.51 g (4.43 mmol) of methanesulfonyl chloride was slowly added dropwise to the system using a constant pressure dropping funnel. The mixture was stirred for 10 min after the addition was completed, and the mixture was once injected into the system. 3 mmol) 2-amino-3,5-difluorobenzoic acid was added, and after stirring for 10 min, 9 mmol) of pyridine was slowly added dropwise using a constant pressure dropping funnel. The dropping process should keep the temperature below 0C. Continue stirring after the addition was complete. 15min, then continue to slowly add 4.5mmol of methanesulfonyl chloride with a constant pressure dropping funnel, stir for 1h after dropping is completed, remove the ice salt bath, the reaction temperature slowly rises to room temperature, after 12h reaction, add water and dichloromethane extraction The organic layer was passed through a column (petroleum ether: ethyl acetate = 10: 1) to give the intermediate 6,8-difluoro-2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl) -4H-benzo[d][1,3]oxazin-4-one.

The synthetic route of 80194-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guizhou University; Wu Jian; Xu Fangzhou; Wang Yanyan; Yu Gang; Xue Wei; Shi Jun; (24 pag.)CN107759518; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 118650-08-1, Adding some certain compound to certain chemical reactions, such as: 118650-08-1, name is Methyl 2-(5-bromopyridin-3-yl)acetate,molecular formula is C8H8BrNO2, 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 118650-08-1.

(5-Bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 58 mg, 0.25 mmol), palladium acetate (3.8 mg, 0.017 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (14 mg, 0.034 mmol), potassium phosphate (108 mg, 0.51 mmol) and water (0.4 mL) were added to a solution of 2-(4-{1-ethyl-1-[3-methyl-4-(4-trimethylsilanyloxy-tetrahydro-thiopyran-4-ylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 136-(4); 100 mg, 0.17 mmol) in toluene (4 mL). The mixture was stirred in a nitrogen stream at 110C for two hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate = 1:3) to give the title compound (82 mg, 79%). 1H-NMR (chloroform-d): 0.23 (s, 9H), 0.65 (t, 6H, J=7.3Hz), 1.96-2.06 (m, 2H), 2.12 (q, 4H, J=7.3Hz) 2.16-2.24 (m, 2H), 2.24 (s, 3H), 2.41 (s, 3H), 2.7-2.8 (m, 2H), 2.8-2.9 (m, 2H), 3.67 (s, 2H), 3.72 (s, 3H), 6.96-7.12 (m, 5H), 7.30 (d, 1H, J=8.0Hz), 7.60-7.64 (m, 1H), 8.47 (d, 1H, J=1.8Hz), 8.52 (d, 1H, J=1.8Hz).

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. 118650-08-1, Methyl 2-(5-bromopyridin-3-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1894911; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53937-02-3, Adding some certain compound to certain chemical reactions, such as: 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone,molecular formula is C12H11NO2, 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 53937-02-3.

To a mixture of tert-butyl 8-bromo-5-methyl-3,4-dihydro-lH-pyrido[4,3-delta]indole- 2(5H)-carboxylate (0.48 g, 1.3 mmol), 4-(benzyloxy)pyridin-2(lH)-one (264 mg, 1.31 mmol), 8-hydroxyquinoline (29 mg, 0.20 mmol), K2CO3 (217 mg, 1.57 mmol) and CuI (38 Attorney’s Docket 2882.023B mg, 0.20 mmol) was added DMSO (5 mL). The reaction mixture was degassed and backfilled with N2. The reaction mixture was heated to 130 0C and stirred at 130 0C overnight. After it was cooled, the mixture was filtered through a layer of Celite. The filtrate was diluted with CH2Cl2, washed with H2O and 5% LiCl, dried with Na2SO4, filtered, and concentrated. Purification by flash column chromatography (silica gel, 5% CH3OH in CH2Cl2) gave the title compound (0.28 g, 44%) as a yellow solid: 1H NMR (500 MHz, CDCl3) delta 7.36-7.29 (m, 8H), 7.13 (d, J= 8.0 Hz, IH), 6.09 (d, J= 2.0 Hz, IH), 6.03 (dd, J = 7.5, 2.0 Hz, IH), 5.05 (s, 2H), 4.61 (s, 2H), 3.84 (m, 2H), 3.66 (s, 3H), 2.82 (m, 2H), 1.49 (s, 9H); ESI MS m/z 486 [M + H]+.

According to the analysis of related databases, 53937-02-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; WO2009/89482; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58530-53-3, 2,4-Dibromopyridine, 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, HPLC of Formula: C5H3Br2N, blongs to pyridine-derivatives compound. HPLC of Formula: C5H3Br2N

Step 1: ethyl 2-[(4-bromopyridin-2-yl)amino]-1,3-oxazole-5-carboxylate To a mixture of 2-amino-oxazole-5-carboxylic acid ethyl ester (0.483 g, 3.09 mmol), tris(dba)dipalladium (O) (0.070 g, 0.077 mmol), xantphos (0.120 g, 0.208 mmol) and cesium carbonate (1.95 g, 5.98 mmol) in 1,4-dioxane (15.0 mL, 192 mmol) was added 2,4-dibromopyridine (1.078 g, 4.55 mmol). The reaction was heated in the microwave at 115 C. for 1 h. The reaction was diluted with DCM (30 mL), silica gel was added to the mixture (11 g) and the solvents were removed to absorb material onto the silica. Purification of sample by column chromatography to afford ethyl 2-[(4-bromopyridin-2-yl)amino]-1,3-oxazole-5-carboxylate (0.561 g, 58%). 1H NMR (400 MHz, DMSO-d6) delta 11.64 (s, 1H), 8.34 (s, 1H), 8.21 (d, J=5.3 Hz, 1H), 7.90 (s, 1H), 7.32 (dd, J=5.3, 1.6 Hz, 1H), 4.29 (q, J=7.1 Hz, 2H), 1.29 (t, J=7.1 Hz, 3H) and ethyl 2-[(2-bromopyridin-4-yl)amino]-1,3-oxazole-5-carboxylate (0.13 g, 14%). 1H NMR (400 MHz, DMSO-d6) delta 11.63 (s, 1H), 8.23 (d, J=5.7 Hz, 1H), 8.01-7.84 (m, 2H), 7.47 (dd, J=5.7, 2.0 Hz, 1H), 4.29 (q, J=7.1 Hz, 2H), 1.29 (t, J=7.1 Hz, 3H).

The synthetic route of 58530-53-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Bharathan, Indu T.; Blackburn, Chris; Ciavarri, Jeffrey P.; Chouitar, Jouhara; Cullis, Courtney A.; D’Amore, Natalie; Fleming, Paul E.; Gigstad, Kenneth M.; Gipson, Krista E.; Girard, Mario; Hu, Yongbo; Lee, Janice; Li, Gang; Rezaei, Mansoureh; Sintchak, Michael D.; Soucy, Francois; Stroud, Stephen G.; Vos, Tricia J.; Wong, Tzu-Tshin; Xu, He; Xu, Tianlin; Ye, Yingchun; US2015/225422; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 145325-40-2, 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.145325-40-2, name is Methyl 4-bromothieno[2,3-c]pyridine-2-carboxylate, molecular formula is C9H6BrNO2S, molecular weight is 272.12, as common compound, the synthetic route is as follows.

Step 3. Methyl thienor2,3-c]pyridine-2-carboxylate. Methyl 4-bromothieno[2,3- c]pyridine-2-carboxylate (115 g, 423 mmol), triethylamine (42.7 g, 423 mmol), THF (1.5 L), and MeOH (500 mL) were mixed and degassed. Under nitrogen, palladium on carbon (10%, 14.7 g, 13.9 mmol) was added. The mixture was hydrogenated with a Parr apparatus at 45 psi H2 for 3 days. The catalyst was filtered off and the filtrate was concentrated to give the desired compound as a white solid (65 g, 80%).

Statistics shows that 145325-40-2 is playing an increasingly important role. we look forward to future research findings about Methyl 4-bromothieno[2,3-c]pyridine-2-carboxylate.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth, W.; BAUMEISTER, Timm, R.; BUCKMELTER, Alexandre, J.; CLODFELTER, Karl, H.; GUNZNER-TOSTE, Janet; HAN, Bingsong; LIN, Jian; REYNOLDS, Dominic, J.; SMITH, Chase, C.; WANG, Zhongguo; ZAK, Mark; ZHENG, Xiaozhang; ZHAO, Guiling; WO2013/130943; (2013); 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. 800401-67-6, name is Ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate, the common compound, a new synthetic route is introduced below. Quality Control of Ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

To a solution of 2-(thietan-3-yl)ethanol (200 mg, 1.69 mmol), tris(butyl)phosphine (6.84g, 10% in hexane, 3.38 mmol) and 1 , l ‘-(azodicarbonyl)dipiperidine (860 mg, 3.38 mmol) in anhydrous tetrahydrofuran (20 mL) was added ethyl 5-chloro-lH-pyrrolo[2,3-c]pyridine-2- carboxylate (380 mg, 1.69 mmol) under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 3 hours. The resulting mixture was then concentrated in vacuo. The residue was purified by flash column (gradient eluting with 0 – 25% ethyl acetate in petroleum ether) to afford 400 mg of ethyl 5-chloro-l-[2-(thietan-3-yl)ethyl]-lH-pyrrolo[2,3-c]pyridine-2- carboxylate as a white solid.

The synthetic route of 800401-67-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Song; GAO, Lu; GUO, Lei; HUANG, Mengwei; LIANG, Chungen; WANG, Baoxia; WANG, Lisha; WU, Guolong; YUN, Hongying; ZHANG, Weixing; ZHENG, Xiufang; ZHU, Wei; WO2014/184163; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 98273-19-9, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 98273-19-9, name is Methyl 4,6-dichloropicolinate. A new synthetic method of this compound is introduced below.

To a solution of methyl 4,6- dichloropyridine-2-carboxylate (1.0 g, 4.9 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.34 g, 0.29 mmol) in THF (11 mL) was added bromo(cyclopropyl)zinc (11 mL of 0.5 M solution in THF, 5.6 mmol). The solution was heated at 60-65 C for 24 h. The solution was allowed to cool to rt, then poured into saturated aqueous ammonium chloride and extracted with EtOAc. The combined organic phases were dried, filtered and concentrated onto Celite. Purification was by silica gel chromatography using 0-15% EtO Ac/hex to afford the title compound (600 mg) as a colorless solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-19-9, Methyl 4,6-dichloropicolinate, and friends who are interested can also refer to it.

Reference:
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17282-40-5, 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 17282-40-5, name is 1-(2-Ethoxy-2-oxoethyl)pyridin-1-ium bromide. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of the corresponding nitroethylene (5 mmol),ethoxycarbonylmethylpyridinium bromide [28] (7.5 mmol), andtriethylamine (15 mmol) in dry acetonitrile (40 mL) was stirred at60 C for 4-5 h (TLC control). Acetonitrile was removed in vacuo, and then methylene chloride (150 mL) was added. The methylenechloride extract was washed with water, 5% aqueous HCl, wateruntil pH 7, and dried by filtration through cotton wool. Methylenechloride was removed in vacuo and the residue was triturated inethanol. The collected crystals werewashed with ethanol and driedin air to obtain a 4,5-dihydroisoxazole 2-oxides 8. When crystallizationwas unavailable, 4,5-dihydroisoxazole 2-oxides 8 were isolatedby column chromatography. For each compound, theappropriate conditions are specified.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 17282-40-5, 1-(2-Ethoxy-2-oxoethyl)pyridin-1-ium bromide.

Reference:
Article; Chernysheva, Natalia B.; Maksimenko, Anna S.; Andreyanov, Fedor A.; Kislyi, Victor P.; Strelenko, Yuri A.; Khrustalev, Victor N.; Semenova, Marina N.; Semenov, Victor V.; European Journal of Medicinal Chemistry; vol. 146; (2018); p. 511 – 518;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem