Day: June 15, 2021

Related Products of 22245-83-6, 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. 22245-83-6, name is 3-(Trifluoromethyl)pyridin-2-ol, molecular formula is C6H4F3NO, 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.

To an ice-cooled solution of 3-(trifluoromethyl)pyridin-2-ol (5 g, 30.7 mmol) in H2SO4 (30 mL, 563 mmol) was added nitric acid (1.507 mL, 33.7 mmol) dropwise. After 30 min, the ice bath was removed and the reaction mixture was stirred at 25 C for 16 h. The reaction mixture was warmed to 60 C for 5 h, cooled, and added to 150 g of ice. The resulting precipitate was collected by filtration, rinsed with additional H20, and air-dried to afford the first batch of product. Another crop of product was obtained after evaporating the mother liquor to less than 100 mL, cooling on an ice bath, and adding NaOH to adjust to pH 8. The mixture was extracted by EA (100 mL). The organic layer was dried and concentrated to give the product, which was combined with the first batch to yield a yellow solid of 5-nitro-3-(trifluoromethyl)pyridin-2-ol (5 g, 24.03 mmol, 78.0% yield): NMR (400 MHz, CD3OD) delta 8.85 (d, J= 3.2 Hz, 1H), 8.58 (d, J= 2.8 Hz, 1H).

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 22245-83-6, 3-(Trifluoromethyl)pyridin-2-ol.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; EIDAM, Hilary Schenck; DEMARTINO, Michael P.; GONG, Zhen; GUAN, Amy Huiping; RAHA, Kaushik; WU, Chengde; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; CHEUNG, Mui; WO2014/141187; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 23056-33-9, 2-Chloro-4-methyl-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, Recommanded Product: 23056-33-9, blongs to pyridine-derivatives compound. Recommanded Product: 23056-33-9

1A. 2-Chloro-5-nitro-isonicotinic acid methyl ester To a solution of 2-chloro-4-methyl-5-nitropyridine (Aldrich Chemical Co.) (5.0 g, 29.0 mmol) in concentrated sulfuric acid (60 mL) with stirring at 0 C was added a solution of sodium dichromate dihydrate (14.3 g, 1.65 eq) in concentrated sulfuric acid (100 mL) at a rate which kept the internal temperature less than 10 C. After addition was complete, the reaction mixture was stirred from 0 C. to room temperature over 6 hours. By TLC, the reaction was not complete, so additional sodium dichromate dihydrate (8.4 g, 1 eq) was added directly to the solution at 0 C. The resulting solution was stirred from 0 C. to room temperature overnight. The reaction was complete by TLC the next morning, and it was poured into a mixture of ice (1 L) and EtOAc (900 mL). The resulting mixture was stirred for about 10 minutes and then the layers were separated. The organic layer was washed with brine (2x 600 mL), and the EtOAc layer was dried over magnesium sulfate and filtered. With stirring at room temperature, trimethylsilyl diazomethathane (2.0M in hexanes, 15 mL) was added to the EtOAc filtrate. The resulting mixture was stirred at room temperature for 30 min. By TLC, there was no acid remaining, and then MeOH (150 mL) was added and the solution stirred for 30 minutes. The solution was concentrated and then EtOAc (700 mL) was added to the residue which was dried over magnesium sulfate, filtered, concentrated and pumped to give the title compound (1A) as an off-white powder (5.79 g, M+=216, M.P.=60.5-64.1C.).

The synthetic route of 23056-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dewdney, Nolan James; Goldstein, David Michael; US2004/209903; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 175205-82-0, 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 175205-82-0 as follows.

2-Bromo-3-(trifluoromethyl)pyridine (1 .5 g, 6.63 mmol) is added to a solution of example 16a (500 mg, 2.21 mmol) in TEA (3.5 mL, 25.25 mmol) and dry ACN (14 mL) at rt. Then Copper (I) Iodide (84 mg, 0.442 mmol) and dichlorobis(triphenylphosphine)palladium(II) (155 mg, 0.221 mmol) are added and stirring is continued overnight. Solvent is evaporated under reduced pressure and the crude is purified byflash chromatography (eluent 0-40% EtOAc/cyclohexane) to furnish the title compound (800 mg, 99%).U PLC-MS (Method 2): R = 1 .23 mm MS (ESI pos): mlz = 363 (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,175205-82-0, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; CUI, Yunhai; DOODS, Henri; FERRARA, Marco; JUST, Stefan; KUELZER, Raimund; LINGARD, Iain; MAZZAFERRO, Rocco; RUDOLF, Klaus; WO2014/184275; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1214334-70-9, 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. 1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid. A new synthetic method of this compound is introduced below.

[0436] To a stirred solution of 5-bromo-6-methoxypicolinic acid (350 mg, 1 mmol) in CH2C12 (2 mL) under an argon atmosphere were added oxalyl chloride (347 mg, 2 mmol) and DMF (catalytic amount) at 0 C. The reaction mixture was stirred at room temperature for 2 h. After consumption of acid (by TLC), the volatiles were evaporated in vacuo to give 5- bromo-6-methoxypicolinoyl chloride.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1214334-70-9, 5-Bromo-6-methoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 230301-11-8 , The common heterocyclic compound, 230301-11-8, name is tert-Butyl 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate, molecular formula is C11H17N3O2, 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 solution of 6-chloro-N-[4-ethyl-5-(4-fluorophenyl)-1H-pyrazol-3-yl]pyrimidin-4-amine (150 mg, 472 muetaiotaomicron) and tert-butyl 1,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate (158 mg, 708 muiotaetaomicron, CAS 230301-11-8) in DMF (2.5 mL) was treated with caesium carbonate (461 mg, 1.42 mmol). The reaction mixture was stirred at 120C overnight and an additional night at 140C. The mixture was diluted with water, three times extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by preparative reverse phase HPLC (method: column: Reprosil CI 8; 10 muiotaeta; 125×30 mm / flow: 50 ml/min / eluent: A = water (0,01% formic acid), B = acetonitrile / gradient: 0.00-5.00 min = 10% B, 6.50 min = 20% B, 17.0-19.75 min = 100% B, 19.75-23.00 min = 90% B). Subsequently the obtained regioisomeric mixture was separated using (HPLC) method to yield 13.2 mg (6% yield) of the desired product. LC-MS (method 9): Rt = 1.18 min; MS (ESIpos): m/z = 505 [M+H]+1H-NMR (400 MHz, DMSO-d6) delta [ppm] : -0.008 (3.40), 0.008 (2.05), 0.988 (1.10), 1.007 (2.36), 1.025 (1.06), 1.073 (0.74), 1.091 (1.48), 1.108 (0.71), 1.424 (16.00), 2.328 (0.41), 2.519 (2.00), 2.524 (1.93), 3.214 (0.83), 3.375 (0.71), 3.392 (0.70), 3.593 (0.62), 3.607 (1.06), 3.621 (0.50), 4.382 (1.39), 7.339 (0.53), 7.361 (1.03), 7.383 (0.62), 7.586 (0.61), 7.600 (0.70), 7.622 (0.53), 7.661 (1.24), 8.459 (0.81), 9.416 (0.72), 12.813 (0.67).

The synthetic route of 230301-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; GIESE, Anja; KLAR, Juergen; EHRMANN, Alexander; WILLWACHER, Jens; ENGEL, David; DIESKAU, Andre Philippe; KAHNERT, Antje; GROMOV, Alexey; SCHMECK, Carsten; LINDNER, Niels; MUeLLER, Thomas; ANDREEVSKI, Anna Lena; DREHER, Jan; COLLINS, Karl; (861 pag.)WO2018/69222; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 54923-31-8, Adding some certain compound to certain chemical reactions, such as: 54923-31-8, name is 5-Bromo-6-methylpyridin-2-ol,molecular formula is C6H6BrNO, 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 54923-31-8.

The 0.60g in the reference embodiment of preparing 7 mentioned in 7A, the 0.38g 3-bromo-6-hydroxy-2-methylpyridine, 0.55g the potassium carbonate and 8 ml of a mixture of acetonitrile in the accompanying 80 C heating and stirring of 4 hours. The water added to the reaction mixture and the mixture is extracted with chloroform. The organic layer with saturated aqueous salt solution washing, drying by anhydrous magnesium sulfate, and concentrated under reduced pressure, to obtain 0.80g of 1-[2-(5-bromo-6-methylpyridine-2-yloxymethyl)-3-methoxyphenyl]-4-methyl-1,4-dihydrotetrazole-5-one(called below 46A).

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. 54923-31-8, 5-Bromo-6-methylpyridin-2-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical Co., Ltd.; Takayuki, Shiota; Masaki, Arimori; (241 pag.)CN105492432; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 571188-59-5, Adding some certain compound to certain chemical reactions, such as: 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate,molecular formula is C14H22N4O2, 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 571188-59-5.

To a solution of compound (11) (200.00 mg, 660.65 mumol, 1.00 eq) in dioxane (10.00 mL), compound (4) (220.67 mg, 792.79 mumol, 1.20 eq), Pd2(dba)3 (60.50 mg, 66.07 mumol, 0.10 eq) and Xantphos (76.45 mg, 132.13 mumol, 0.20 eq) and cesium carbonate (430.51 mg, 1.32 mmol, 2.00 eq) were added. The solution was heated to 110 C. under the protection of nitrogen gas and stirred for 16 hours. LCMS showed that the reaction was complete. The solution was cooled to 25 C., filtered and concentrated to obtain a crude product. The crude product was purified by preparative TLC (ethyl acetate:petroleum ether=1: 2) to obtain compound (12) (320.00 mg, 587.57 mumol, yield: 88.94%). LCMS (ESI) m/z: 545.3 (M+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. 571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; Ding, Charles Z.; Chen, Shuhui; Hu, Lihong; Xu, Zhaobing; Liu, Yingchun; Ren, Bingjie; Li, Weidong; Li, Zongbin; Zhao, Rui; Zhang, Xiquan; (21 pag.)US2019/194168; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 7295-76-3, 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. 7295-76-3, name is 3-Methoxypyridine, molecular formula is C6H7NO, 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: To a stirred, cooled (0 C) solution of 2,2,6,6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in THF (2-3 mL) were successively added BuLi (about 1.6 M hexanes solution, 1.5 mmol) and, 5 min later, ZnCl2TMEDA[51] (0.13 g, 0.50 mmol). The mixture was stirred for 15 min at 0 C before introduction of the substrate (1.0 mmol) at 0-10 C. After 2 h at room temperature, a solution of I2 (0.38 g, 1.5 mmol) in THF (4 mL) was added. The mixture was stirred overnight before addition of an aqueous saturated solutionof Na2S2O3 (4 mL) and extraction with AcOEt (320 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. Purification by chromatographyon silica gel (the eluent is given in the product description) led to the compounds described below.

According to the analysis of related databases, 7295-76-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hedidi, Madani; Bentabed-Ababsa, Ghenia; Derdour, Aicha; Halauko, Yury S.; Ivashkevich, Oleg A.; Matulis, Vadim E.; Chevallier, Floris; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence; Tetrahedron; vol. 72; 17; (2016); p. 2196 – 2205;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 154048-89-2 , The common heterocyclic compound, 154048-89-2, name is N-Boc-3-Amino-4-iodopyridine, molecular formula is C10H13IN2O2, 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.

Alternate Preparation: Tert-butyl 2-((benzyloxy)methyl)-lH-pyrrolo[2,3- c]pyridine-l-carboxylate was also prepared in an alternate preparation directly from tert-butyl tert-butyl (4-iodopyridin-3-yl)carbamate: In a sealed tube was added ((prop-2-yn-l-yloxy)methyl)benzene (104 mu, 0.750 mmol) and tert-butyl (4- iodopyridin-3-yl)carbamate (200 mg, 0.625 mmol) in DMF (625 mu). To this was added PdCl2(PPh3)2 (21.93 mg, 0.031 mmol), copper(I) iodide (11.90 mg, 0.062 mmol) and TEA (1742 mu, 12.50 mmol). This reaction was then degassed for 15 minutes and then allowed to stir at 80 C sealed. After 4 hours the reaction was complete. The reaction mixture was poured into ethyl acetate and saturated ammonium chloride. The organic was collected and washed several times with ammonium chloride. The organic was then purified on the biotage eluting in 10% ethyl acetate for 10 column volumes and then 10%-40% Ethyl acetate in hexanes over 10 column volumes. The product, tert-butyl 2-((benzyloxy)methyl)-lH- pyrrolo[2,3-c]pyridine-l-carboxylate (179 mg, 85% yield) was collected as a dark yellow oil. 1H NMR (400MHz, CHLOROFORM-d) delta = 9.58 – 9.20 (m, 1H), 8.70 – 8.42 (m, 1H), 7.54 – 7.34 (m, 6H), 6.78 (s, 1H), 4.98 (d, J=1.3 Hz, 2H), 4.73 (s, 2H), 1.69 (s, 9H).

The synthetic route of 154048-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MCDONALD, Ivar, M.; OLSON, Richard, E.; MATE, Robert, A.; WO2015/191401; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53234-55-2, 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. 53234-55-2, name is 5-Cyanopicolinic acid, molecular formula is C7H4N2O2, 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.

To a solution of 5-cyanopicolinic acid (1 g, 6.75 mmol) in dry THF (10 mL) at -15C was added Et3N (0.68 g, 6.75 mmol), ethyl chloro formate (0.73 g, 6.75 mmol),and the mixture was stirred for 16 hours at -15C. Ether (15 mL), TMSCHN2 (1.54 g, 13.5 mmol) was added, and the mixture was stirred overnight while returning to room temperature. After completion, the reaction mixture was diluted with EtOAc (75 mL), washed with water (50 mL), brine (40 mL), dried over anhydrous Na2SO4, filtered andevaporated. The diazaketone was dissolved in dioxane:H20 (1:1) (10 mL), added AgCOOPh (cat), and the mixture was stirred at 100C for 16 hours. After completion, the reaction mixture was diluted with EtOAc (50 mL), acidified using iN HC1 and extracted using EtOAc (2 x 50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude compound was purified by triturating with ether (10 mL) and pentane (50mL) to afford 2-(5-cyanopyridin-2-yl) acetic acid (350 mg, 32 %) as yellow solid.

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 53234-55-2, 5-Cyanopicolinic acid.

Reference:
Patent; NUEVOLUTION A/S; SCHROeDER GLAD, Sanne; GROeN NOeRAGER, Niels; SARVARY, Ian; HAAHR GOULIAEV, Alex; TEUBER, Lene; STASI, Luigi, Piero; (244 pag.)WO2016/20288; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem