Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 1033202-51-5, 5-Fluoro-3-nitropicolinonitrile, 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, 1033202-51-5, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Fluoro-3-nitropicolinonitrile

Tin dichloride (45 g, 230 mmol) was added to a solution of 5-fluoro-3-nitropyridine-2-carbonitrile (Ark Pharm, 7.2 g, 43 mmol) in EtOH (80 mL). The mixture was stirred at 90 C. for 2 h, and then concentrated under reduced pressure. Aq. HCl (10 M; 40 mL, 400 mmol) was then added and the mixture was heated under reflux for 6 h. The reaction mixture was then concentrated under reduced pressure and the resulting residue was dissolved in MeOH (120 mL). Thionyl chloride (7.2 mL, 99 mmol) was added. The solution was then stirred at 90 C. for 24 h. The reaction mixture was concentrated under reduced pressure, diluted with EtOAc (300 mL), washed with a saturated aq. NaHCO3 (300 mL) and brine (200 mL), dried over Na2SO4 and concentrated again under reduced pressure. The resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes) to afford the sub-title compound (4.6 g, 63%). LCMS calc. for C7H8FN2O2 (M+H)+: m/z=171.0. found 171.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1033202-51-5, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; Xue, Chu-Biao; Li, Yun-Long; Geng, Hao; Pan, Jun; Wang, Anlai; Zhang, Ke; Yao, Wenqing; Zhang, Fenglei; Zhuo, Jincong; US2014/200227; (2014); 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. 69045-78-9, name is 2-Chloro-5-(trichloromethyl)pyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 69045-78-9

Example 3 In a 119.5 cc autoclave equipped with a magnetic stirrer, 2-chloro-5-trichloromethylpyridine (11.5 g), Raney nickel (1.15 g), ethylenediamine (21.0 g) and ethanol (20 g) were charged. Hydrogen gas was introduced into the autoclave to a pressure of 10 Kg/cm2, and an internal temperature was raised to 45 C. At the same temperature, the hydrogen gas was supplied under a hydrogen pressure of 7 to 11.2 Kg/cm2. The absorption of hydrogen ceased after 180 minutes from the start of hydrogen supply. After completion of reaction, the autoclave was cooled down to room temperature, and the catalyst was filtrated off from the reaction mixture. The filtrate was adjusted to pH 13.7 with a 48% aqueous solution of sodium hydroxide and the filtrate was concentrated. The concentrate was analyzed by gas chromatography to find that a yield of 2-chloro-5-(2-aminoethyl)aminomethylpyridine was 10%.

The synthetic route of 69045-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Koei Chemical Co., Ltd.; US5424437; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1026796-81-5, N-(4-Bromopyridin-2-yl)acetamide, 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, 1026796-81-5, blongs to pyridine-derivatives compound. Application In Synthesis of N-(4-Bromopyridin-2-yl)acetamide

To the stirred solution of 3 -methyl- l-(6-(trimethy lstannyl)naphthalen-2- yl)butan-l-ol (0.080 g, 0.212 mmol) and (4-bromopyridin-2-yl)acetamide (0.046 g, 0.212 mmol) in anhydrous DMF (2 mL) was added tetrabutylammonium bromide (0.103 g, 0.318 mmol), bis(triphenylphosphine)palladium (II) chloride (0.019 g, 0.021 mmol), K2C03 (0.088 g, 0.636 mmol) and the mixture purged with nitrogen for 5 min then heated at 95 C for 14 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over Na2S04 and evaporated under reduced pressure. The residue was purified by preparative HPLC (0.1 % TF A in water and acetonitrile) to afford N-(4-(2-( 1 -hydroxy-3 – methylbutyl)quinolin-6-yl)pyridin-2-yl)acetamide, TFA (9 mg, 0.026 mmol, 12% yield). 1H NMR (400 MHz, CD3OD) delta ppm 8.98 (d, J= 8.8 Hz, 1H) 8.65 (d, J= 1.6 Hz, 1H) 8.40 – 8.49 (m, 3H) 8.30 (s, 1H) 8.04 (d, J= 8.8 Hz, 1H) 7.77 – 7.79 (m, 1H) 5.21 – 5.24 (m, 1H) 2.31 (s, 3H) 2.01 – 2.04 (m, 1H) 1.80 – 1.87(m, 1H) 1.69 – 1.75 (m, 1H) 1.00 – 1.12 (m, 6H); LCMS (ESI) m/e 350.2 [(M+H)+, calcd for C21H2 N3O2, 350.2]; LC/MS retention time (method A): tR = 1.62 min; HPLC retention time (method A): tR = 11.25 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1026796-81-5, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; MACOR, John E.; BRONSON, Joanne J.; DASGUPTA, Bireshwar; DZIERBA, Carolyn Diane; NARA, Susheel Jethanand; KARATHOLUVHU, Maheswaran Sivasamban; WO2015/116492; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 884494-51-3, 2-Fluoro-4-iodonicotinic acid, 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, COA of Formula: C6H3FINO2, blongs to pyridine-derivatives compound. COA of Formula: C6H3FINO2

Step 1: Methyl 2-(((3R,6R)-1-(tert-butoxycarbonyl)-6-methylpiperidin-3-yl)oxy)-4-iodonicotinate (15) A solution of 2-fluoro-4-iodonicotinic acid (0.651 g, 2.44 mmol) in DMF (3 mL) was treated with sodium hydride (0.072 g, 3.0 mmol). After stirring ~5 minutes, tert-butyl (2R,5R)-5- hydroxy-2-methylpiperidine-1-carboxylate (Example 2, 8, 0.500 g, 2.32 mmol) and sodium hydride 10 (0.072 g, 3.0 mmol) were added, and the reaction was heated to 40 C for 1 hour. Iodomethane (0.73 mL, 0.012 mmol) was added, and the reaction was stirred at RT. After 1 hour, the mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography eluting with 0-20% ethyl acetate in hexanes to provide the title compound as a colorless oil. LRMS m/z (M+H) 477.2 found, 477.2 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-51-3, 2-Fluoro-4-iodonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2015/88864; (2015); 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. 1033202-51-5, name is 5-Fluoro-3-nitropicolinonitrile, the common compound, a new synthetic route is introduced below. Recommanded Product: 5-Fluoro-3-nitropicolinonitrile

Step A. Methyl 3-amino-6-fluorothieno[3,2-b]pyridine-2-carboxylate To a solution of 5-fluoro-3-nitropyridine-2-carbonitrile (2.00 g, 12.0 mmol) in DMF (30 mL) at 0 C. was added 2-mercaptoacetic acid methyl ester (1.13 mL, 12.6 mmol) followed by a solution of potassium hydroxide (1.34 g, 23.9 mmol) in water (3.0 mL) dropwise. The reaction mixture was stirred at 0-5 C. for 1 h. The mixture was quenched with water and extracted with EtOAc (2 times). The combined organic phases were washed with water and brine, dried over Na2SO4 and concentrated under reduced pressure to give 2.68 g (99% yield) of the sub-title compound as a yellow solid. LCMS calc. for C9H8FN2O2S (M+H)+: m/z=227.0. found: 227.1.

The synthetic route of 1033202-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; Li, Yun-Long; Burns, David M.; Feng, Hao; Huang, Taisheng; Mei, Song; Pan, Jun; Vechorkin, Oleg; Ye, Hai-Fen; Zhu, Wenyu; Rafalski, Maria; Wang, Anlai; Xue, Chu-Biao; US2015/57265; (2015); 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 1003711-43-0, name is 2-Bromo-5-hydroxy-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1003711-43-0

(A) To an ice-cooled solution of 6-bromo-5-methylpyridin-3-ol (500 mg, 2.66 mmol) in DMF (10 mL) was added NaH (60% wt; 160 mg, 4.0 mmol) in a portionwise fashion and the resultant mixture was allowed to stir at rt for 1 h. The mixture was then cooled to 0 C. and CH3I (755 mg, 5.32 mmol) was added in dropwise fashion. After stirring for 1 h at rt, the reaction was quenched with water (20 mL) and the mixture was extracted with EtOAc (3*30 mL). The combined extracts were dried (Na2SO4), concentrated under reduced pressure and purified by silica gel chromatography (0-10% EtOAc/petroleum ether) to afford 2-bromo-5-methoxy-3-methylpyridine (400 mg, 74% yield) as a white solid. LC/MS: mass calcd. for C7H8BrNO: 202.05, found: 202.0, 204.0 [M, M+2]+.

With the rapid development of chemical substances, we look forward to future research findings about 1003711-43-0.

Reference:
Patent; Janssen Pharmaceutica NV; Liang, Yin; Demarest, Keith T.; (109 pag.)US2017/290800; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 130473-26-6, Adding some certain compound to certain chemical reactions, such as: 130473-26-6, name is 1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde,molecular formula is C8H6N2O, 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 130473-26-6.

C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid. The solution is cooled in an ice bath, 30% aqueous hydrogen peroxide (722 muL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5 C. The mixture is diluted with H2O, the solid is collected, washed with H2O and is dried to give 522 mg of an off-white solid. The formate salt is added to 7 mL H2O, 3 mL 2N NaOH is added, and the pH is adjusted to 3 with 5% aqueous HCl. The precipitate is collected and is dried to afford 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (C176) (67% yield). HRMS (FAB) calculated for C8H6N2O2+H: 163.0508, found 163.0507 (M+H). Example 23(i) can be obtained by coupling either exo-[2.2.1]-3-Amine or endo-[2.2.1]-3-Amine with C176.

According to the analysis of related databases, 130473-26-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Walker, Daniel Patrick; Piotrowski, David W.; Jacobsen, Eric Jon; Acker, Brad A.; Wishka, Donn G.; Reitz, Steven Charles; Groppi JR., Vincent E.; US2003/153595; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 138647-49-1, tert-Butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate, 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: 138647-49-1, blongs to pyridine-derivatives compound. Recommanded Product: 138647-49-1

B. Methyl 1-boc-1,2,3,6-Tetrahydro-4-pyridinecarboxylate To a stirred solution of 1-Boc-1,2,3,6-tetrahydro-4-[(trifluoromethyl)sulfonyloxy]pyridine (74.84 g, 226 mmol) in N,N-dimethylformamide (60 mL) was added triethylamine (4.2 mL, 30.2 mmol), palladium acetate (0.100 g, 0.45 mmol), triphenylphosphine (0. 235 g, 0.9 mmol), and methanol (24.5 mL) and the solution was placed under an atmosphere of carbon monoxide. After stirring for 48 h, the solvent was removed in vacuo. The residue was chromatographed over silica gel, eluding with 5-10% ethyl acetate in hexane. The product containing fractions were combined and concentrated in vacuo to give 2.35 g (65%) of the title compound as a clear oil. 1H-NMR; FD-MS, m/e 240.2 (m); Analysis for C12H19NO4: Calcd: C, 59.74; H, 7.94; N, 5.81; Found: C, 59.60; H, 8.07; N, 5.85.

The synthetic route of 138647-49-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US6635657; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 183208-34-6 , The common heterocyclic compound, 183208-34-6, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one, molecular formula is C7H5BrN2O, 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 the 250 ml flask is sequentially added in 50 ml ethanol and 5 – bromo -1 – hydrogen pyrrolo [2,3 – the b] pyridine -2 – ketone (4.2g, 20 mmol), Sn powder (4.7 g, 40 mmol) and 5 mol/L hydrochloric acid (14 ml), 40 C stirring for 2 hours, the reaction is completed, to remove the ethanol, add 50 ml of water residue is completely dissolved, saturatedNaHCO3solution and to PH=8, and filtering the resulting solid, after drying, dissolved in 50 ml chloroform, addingCuBr2(13.4 g, 60mmol), 60 Cstirring for 2 hours, the reaction is completed, the end of the reaction, rotary evaporated to remove chloroform, adding 50 ml saturatedNaHCO3solution, ethyl acetate (3 × 100 ml), the combined organic phase with water (50 ml) for washing and then the saturated salt water (50 ml) washing, anhydrousNa2SO4drying, filtering, the filtrate is concentrated to obtain 5 – bromo – 1H – pyrrolo [2,3 – the b] pyridine the crude product, the crude product is chloroform: hexane=2:1 (volume ratio) mixed solution recrystallize to get 3.1 g of pale yellow 5 – bromo – 1H – pyrrolo [2,3 – the b] pyridine pure product, yield 77.6%, melting point:176.8-177.3 C,

The synthetic route of 183208-34-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Heze University; Fan, Hongli; Li, Fenghai; Xu, Meiling; Guo, Qianqian; (7 pag.)CN106045995; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 97316-50-2, Ethyl 4-cyanopicolinate, 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: Ethyl 4-cyanopicolinate, blongs to pyridine-derivatives compound. Recommanded Product: Ethyl 4-cyanopicolinate

EXAMPLE 10 Production of 2-(4-cyano-2-pyridyl)-4,4-bis(4-fluorophenyl)-2-imidazoline The mixture of 1,1-bis(4-fluorophenyl)-1,2-ethanediamine(153 mg) and 4-cyano-2-ethoxycarbonylpyridine(95 mg) was stirred at 180 C. for 2 hours. The obtained oily compound was purified by silica gel column chromatography (C-300; hexane:ethyl acetate=3:2) to give the objective compound (103 mg). Melting point: 206-208 C.

The synthetic route of 97316-50-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sato, Nagaaki; Okamoto, Osamu; Jitsuoka, Makoto; Nagai, Keita; Kanatani, Akio; Ishihara, Akane; Ishii, Yasuyuki; Fukami, Takehiro; US2003/158418; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem