Month: April 2022

Reference of 121643-44-5, 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. 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, molecular formula is C7H6F3NO, 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.

2-Methoxy-3-trifluoromethyl-pyridine (2.7 g, 14.79 mmol) and 1 ,3-dibromo-5,5- dimethylhydantoin (5.28g, 18.48 mmol) were placed in a round-bottom flask. To this mixture was slowly added 40ml TFA. The mixture was stirred overnight at ambient temperature (16h). After completion of the reaction, TFA solvent was evaporated in vacuo and the resulting residue was neutralized to pH6-7 by the addition of saturated NaHC03. The aqueous layer was extracted with DCM two times and the combined extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give a mixture of oil and white solid. The residue was redissolved into 20% Ethylacetate/Heptane (50ml) and the insoluble white solid was filtered off. The filtrate was concentrated and then purified by Flash- chromatography on silica gel (EtOAc/Heptane 5/95) to give 5-Bromo-2-methoxy-3- trifluoromethyl-pyridine as a colorless liquid (2.08 g, 52% yield).1 H-NMR (400 MHz, DMSO-d6, 298 K): ? ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 H).

According to the analysis of related databases, 121643-44-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; LEWIS, Ian; SMITH, Alexander, Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; WOLF, Romain; ZECRI, Frederic; WO2013/57711; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 59782-86-4, Adding some certain compound to certain chemical reactions, such as: 59782-86-4, name is 2-Chloro-5-iodonicotinic acid,molecular formula is C6H3ClINO2, 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 59782-86-4.

To a solution of 2-chloro-5-iodonicotinicacid (1 g, 3.38 mmol), 3-(difluoromethyl)-4-methyl-benzylamine (876 mg, 4.22 mmol), and DIPEA (1.8 mL) in DMF (10 mL) cooled at 0C was added BOP reagent (1.65 g,3.73 mmol). The mixture was stirred at 0C for 2 h and atroom temperature for 1 h and diluted with a mixture of EtOAc(100 mL) and n-hexane (50 mL). The organic solution waswashed with water, saturated aqueous NaHCO3 and brine,dried over Na2SO4, and concentrated in vacuo. 2-Propanol(15 mL) was added to the residual solid, and the resultingsuspension was stirred at room temperature for 1 h. The precipitates were collected by filtration to yield 7 (1.11 g, 76%) as pale yellow solid. 1H-NMR (400 MHz, DMSO-d6) delta: 9.17 (1H, t, J=6.0 Hz),8.73 (1H, d, J=2.3 Hz), 8.29 (1H, d, J=2.3 Hz), 7.52 (1H, br s),7.41 (1H, br d, J=7.7 Hz), 7.15 (1H, t, J=55.0 Hz), 7.29 (1H,br d, J=7.7 Hz), 4.46 (2H, d, J=6.0 Hz), 2.37 (3H, s). MS (ESI)m/z: 436.9 (M+H)+. HPLC purity 94.8% (4.37 min, method B).

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. 59782-86-4, 2-Chloro-5-iodonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Takahashi, Bitoku; Funami, Hideaki; Shibata, Makoto; Maruoka, Hiroshi; Koyama, Makoto; Kanki, Satomi; Muto, Tsuyoshi; Chemical and Pharmaceutical Bulletin; vol. 63; 10; (2015); p. 825 – 832;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1227588-59-1 ,Some common heterocyclic compound, 1227588-59-1, molecular formula is C6H3BrFNO, 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.

General procedure: To a solution of 1Himidazole4carbaldehyde (0.50 g, 5.20 mmol) and 6chloro4methoxynicotinonitrile (1.05 g, 6.24 mmol) in DMF (10 mL) was added K2CO3 (1.08 g, 7.81 mmol) at ambient temperature under a nitrogen atmosphere. The resulting reaction mixture was heated at 90C for 1 h. The reaction mixture was cooled to ambient temperature and diluted with ice water (30 mL). The resulting precipitate was filtered and was washed with ethanol (2 mL) to obtained Intermediate 11 (0.30 g, 25.00%).1H NMR (400 MHz, DMSOd6) G ppm 4.13 (s, 3 H), 7.81 (s, 1 H), 8.83 (s, 2 H), 8.95 (d, J = 1.19 Hz, 1 H), 9.87 (s, 1 H). LCMS (MethodL): retention time 0.75 min, [M+H] 229.1.

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. 1227588-59-1, 6-Bromo-5-fluoronicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1020253-14-8, 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. 1020253-14-8, name is 6-Chloro-5-fluoronicotinonitrile, molecular formula is C6H2ClFN2, 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.

Step 1: 6-(3-(2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)-3-hydroxyazetidin-1-yl)-5-fluoronicotinonitrile (0252) 44 3-(2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)azetidin-3-ol hydrochloride (3c, 200 mg, 0.4 mmol), 84 6-chloro-5-fluoronicotinonitrile (74.8 mg, 0.48 mmol), 23 potassium carbonate (247 mg, 4.0 mmol) and 8 DMF (2 mL) were combined and the mixture was heated at 80 C. for 3 hrs in a sealed tube. 31 Water (20 mL) was added and the resulting mixture was extracted with EtOAc (50 mL×3), the combined organic phases were washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Silica gel column chromatography gave the desired 85 product.

According to the analysis of related databases, 1020253-14-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Sciences, Inc.; Blomgren, Peter A.; Currie, Kevin S.; Farand, Julie; Gege, Christian; Kropf, Jeffrey E.; Xu, Jianjun; (35 pag.)US2017/355693; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 696-42-4, 5-Fluoronicotinonitrile, 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: C6H3FN2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H3FN2

General procedure: (Reference Example 35) 5-[4-(5-Amino-1H-pyrazol-3-yl)piperidin-1-yl]pyridine-3-carbonitrileThe title compound (0.167 g, yield: 37%) was obtained through reaction in the same way as the method described in Reference Example 34 using 5-fluoropyridine-3-carbonitrile (0.204 g, 1.67 mmol) instead of 3,6-dichloropyridazine. 1H-NMR (400 MHz, DMSO-d6) delta: 11.13 (1H, brs), 8.59 (1H, d, J = 3 Hz), 8.28 (1H, d, J = 2 Hz), 7.78 (1H, dd, J = 3 Hz, 2 Hz), 5.20 (1H, brs), 4.45 (2H, brs), 3.94-3.87 (2H, m), 2.93-2.85 (2H, m), 2.73-2.64 (1H, m), 1.94-1.87 (2H, m), 1.65-1.55 (2H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,696-42-4, 5-Fluoronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Daiichi Sankyo Company, Limited; KOBAYASHI, Hideki; OHKAWA, Nobuyuki; TAKANO, Daisuke; KUBOTA, Hideki; ONODA, Toshio; KANEKO, Toshio; ARAI, Masami; TERASAKA, Naoki; EP2862861; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59020-10-9, 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.59020-10-9, name is 3-(Tributylstannyl)pyridine, molecular formula is C17H31NSn, molecular weight is 368.1447, as common compound, the synthetic route is as follows.

General procedure: Aryl halide (0.5 mmol), base (1 mmol), CuI (20 mol %), alkylstannylpyridine(0.75 mmol), and catalyst (1 mol %) were dissolvedin DMF (2 mL) in a 10 mL vial and heated at a specific temperatureunder N2 for 12 h. After the reaction was complete, and thenquenched with water. The mixture was diluted with ethyl acetate(10 mL), filtered through a pad of Celite, and followed by extractionwith ethyl acetate for three times. The combined organic layer wasdried over anhydrous Na2SO4, filtered, and evaporated under reducedpressure. The residual was purified by flash chromatographyon silica gel (ethyl acetate/hexane) to give the desired product.

Statistics shows that 59020-10-9 is playing an increasingly important role. we look forward to future research findings about 3-(Tributylstannyl)pyridine.

Reference:
Article; Ma, Gaizhi; Leng, Yuting; Wu, Yusheng; Wu, Yangjie; Tetrahedron; vol. 69; 2; (2013); p. 902 – 909;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1187322-51-5, 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.1187322-51-5, name is 6-Amino-5-iodonicotinonitrile, molecular formula is C6H4IN3, molecular weight is 245.02, as common compound, the synthetic route is as follows.

To the solution of 3-iodo-5-isocyanopyridin-2-amine (2.74 g, 11.2 mmol, 1 eq) in anhydrous dimethylformamide (25 mL) in a 100 mL round bottom flask was added ammonium chloride (1.02 g, 1.7 eq) and sodium azide (1.24 g, 1.7 eq). The resulting reaction mixture was heated to 100 C. under nitrogen for 20 hours. After the reaction mixture was cooled to room temperature, it was poured into ice-chunk filled water and the pH of the mixture was adjusted to ?3.5 using aqueous hydrochloric acid (2 N). After the mixture was stirred at room temperature for about two hours, it was filtered through a Buchner funnel, rinsed with water, giving a brown solid. The solid was treated with MeOH-CHCl3 and concentrated down with silica gel. Upon gradient column chromatography (MeOH-EtOAc 1:20 to 1:5), 3-iodo-5-(2H-tetrazol-5-yl)pyridin-2-amine was obtained as off-white solid in the amount of 1.15 g. 1H NMR (600 MHz, DMSO-d6) delta ppm 8.60 (d, J=1.76 Hz, 1H) 8.45 (d, J=2.05 Hz, 1H) 6.77 (br. s., 2H).

Statistics shows that 1187322-51-5 is playing an increasingly important role. we look forward to future research findings about 6-Amino-5-iodonicotinonitrile.

Reference:
Patent; Allergan, Inc.; Boral, Sougato; Malone, Thomas C.; Wang, Shimiao; Rao, Sandhya; Yang, Rong; (28 pag.)US2016/102081; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 483324-01-2, 2-Chloro-4-(pyridin-3-yl)pyrimidine, 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, Formula: C9H6ClN3, blongs to pyridine-derivatives compound. Formula: C9H6ClN3

Preparation of 4-pyridin-3-yl-pyrimidin-2-ylamine lll-b In a sealed tube, a solution of lll-a (1 .18 g, 6.16 mmol) in 30percent NH4OH (12 mL) was heated at deltaOmicron ‘ for 16h. After cooling, the precipitate was isolated by filtration, washed with water and dried under vacuum to give the title compound lll-b as a beige solid (925 mg, 87 percent). H NMR (400 MHz, DMSO-d6) delta 9.23 (d, J = 2.1 Hz, 1 H), 8.69 (dd, J = 4.7, 1 .3 Hz, 1 H), 8.43 – 8.38 (m, 1 H), 8.36 (d, J = 5.1 Hz, 1 H), 7.53 (dd, J = 8.0, 4.8 Hz, 1 H), 7.21 (d, J = 5.1 Hz, 1 H), 6.76 (s, 2H).

The synthetic route of 483324-01-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AB SCIENCE; MOUSSY, Alain; BENJAHAD, Abdellah; SCHALON, Claire; PEZ, Didier; CHEVENIER, Emmanuel; SANDRINELLI, Franck; MARTIN, Jason; PICOUL, Willy; WO2014/202763; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1075-62-3 ,Some common heterocyclic compound, 1075-62-3, molecular formula is C7H9N3O, 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.

In a 25 mL round bottom flask, 5-(methoxymethylene)-2,2-dimethyl-i,3-dioxane- 4,6-dione (6.06 g, 32.5 mmol) was added to a stirred mixture of N-(6-aminopyridin-2- yl)acetamide (4.10 g, 27.1 mmol) in EtOH (5 ml) at room temperature. After the reaction mixture was stirred at 80C for 3 hr, it was cooled down to room temperature and then concentrated under vacuum to give the title compound as a solid. LCMS (ESI) calc?d for C,4H,5N305 [M+i ]: 306,found: 306; ?H NMR (300 MHz, CDC13): oei i.18(s, 1H), 9.27 (d, J= 4.2 Hz, 1H), 8.06 (d, J= 8.4 Hz, 1H), 7.90 (s,1H),7.77-7.72(m,1H), 6.73 (d, J= 7.8 Hz, 1H),2.26 (s,3H), 1.76 (s,6H).

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. 1075-62-3, N-(6-Aminopyridin-2-yl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BENNETT, Frank; JIANG, Jinlong; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; SCOTT, Jack D.; TANG, Haiqun; ZHAO, Zhiqiang; HUANG, Yuhua; HUNTER, David; YANG, Dexi; ZHANG, Zhibo; FU, Jianmin; BAI, Yunfeng; ZHENG, Zhixiang; ZHANG, Xu; YOUNG, Katherine; XIAO, Li; (580 pag.)WO2016/206101; (2016); 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.945954-94-9, name is Methyl 6-bromo-3-methoxypicolinate, molecular formula is C8H8BrNO3, molecular weight is 246.06, as common compound, the synthetic route is as follows.HPLC of Formula: C8H8BrNO3

(step .4); To a solution of the compound obtained in step 3 (7.56 g) in THF (110 mL) was added diisobutylaluminum hydride (DIBAL-H) ( 1.5M toluene solution, 24.6 mL) at -78C, and the mixture was stirred at -78C for 1 hr. To the reaction mixture was added saturated aqueous Rochelle salt, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 0->33% ethyl acetate/hexane) and crystallized from ethyl acetate/hexane to give 6-bromo-3-methoxypyridine-2- carbaldehyde (5.36 g, 81%) as white crystals,

At the same time, in my other blogs, there are other synthetic methods of this type of compound,945954-94-9, Methyl 6-bromo-3-methoxypicolinate, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/89031; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem