Day: April 8, 2022

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

Adding a certain compound to certain chemical reactions, such as: 878197-68-3, 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde, 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: C8H5BrN2O, blongs to pyridine-derivatives compound. Formula: C8H5BrN2O

The reactor is charged with N-methylpiperazine (3.1 Kg, 31 mol ) and tetrahydrofuran (10 Liters) and stirred under nitrogen while cooling to negative 20 0C. n-Butyl lithium (10.4 L, 26.0 mol) is added to the reaction at a rate to maintain the negative 20 0C temp and the contents are stirred for 15 to 30 minutes. A slurry of 5- bromoimidazo[1 ,2-a]pyridine-2-carbaldehyde (2.79 Kg, 12.4 mol) in tetrahydrofuran (10 Liters) is added at a rate to maintain the reaction at ?0C. The slurry is washed in with additional tetrahydrofuran (6 Liters). The reaction is stirred for 30 minutes and warmed to approximately negative 10 0C. The reaction is quenched by addition of 6N HCI solution to achieve pH 4.0 while maintaining at ? 150C. The reaction is diluted with heptane (14 Liters) and the layers allowed to separate. The lower aqueous layer is drained and the upper organic layer is washed with 1 N HCI (2 x 1.5 Liters). The combined aqueous layers are stirred at 20 degrees and adjusted to pH 9 with 4N NaOH solution. The Aqueous layer is extracted with 10% iPrOH/CH2CI2 (3 x 28 Liters) and the combined organic layers are washed with saturated NaHCO3 solution (14 Liters) and evaporated at <25 0C to approximately 3 volumes, lsopropanol (28 Liters) is added and reaction again concentrated under reduced pressure to approximately 8.5 Liters, lsopropanol (17 Liters) is added and the reaction is treated with a solution of oxalic acid (1.0 Kg, 11.1 mol) in isopropanol (7 Liters) at a rate to maintain good stirring and temperature between approximately 25-4O0C. The reaction is stirred for 30 minutes and the solids are collected and washed with isopropanol (8.5 Liters) Solids are dried at 50 0C to yield 5-(4-methyM- piperazinyl)imidazo[1 ,2-a]pyridine-2-carbaldehyde, (2.25 Kg, 54% yield) 1 H NMR (400 MHz, DMSO-D6) delta ppm 10.01 (s, 1 H) 8.47 (s, 1 H) 7.41 (m, 2 H) 6.65 (m, 1 H) 3.34 (s, 8 H) 2.78 (s, 3 H) At the same time, in my other blogs, there are other synthetic methods of this type of compound,878197-68-3, 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde, and friends who are interested can also refer to it. Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/26703; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 167837-43-6 , The common heterocyclic compound, 167837-43-6, name is (E)-3-(6-Aminopyridin-3-yl)acrylic acid, molecular formula is C8H8N2O2, 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.

EDC (231 mg, 1.2 mmol) was added to a solution of (E)-3- (6-amino-pyridin-3- yl) acrylic acid (164 mg, 1.0 mmol), (2-propoxy-3-methoxy-benzyl) methylamine (230 mg, 1.1 mmol), HOBT’H20 (149 mg, 1.1 mmol) and DIPEA (525 L) L, 3.0 mmol) in dry DMF (10 mL). After 18 hr of stirring, the mixture was diluted with water (60 mL) and extracted with EtOAc (2X20 mL). The organic layer was washed with brine (2X30 mL), dried and evaporated. Flash chromatography (silica 1-3% MEOH in CH2CL2) furnished pure free base which was dissolved in CHZCLZ (10 mL). After addition of HCl (1.5 mL, 1M in ether), the solvents were evaporated; the residue was washed with ether and dried to afford the title compound (185 mg, 47%). 1H NMR (300 MHz, DMSO-d6) 8 8.16 (m, 3H), 7.48 and 7.45 (rotamers, 2d, J= 15.4 Hz, 1H), 7.23 (d, J= 15. 4 Hz, 1H), 7.00 (m, 3H), 6.61 (m, 1H), 4.78 and 4.63 (rotamers, 2s, 2H), 3.87 (m, 2H), 3.79 (s, 3H), 3.09 and 2.85 (rotamers, 2s, 3H), 1.71 (m, 2H), 0.97 (m, 3H). MS (ESI) M/E 356 (M+H) +.

The synthetic route of 167837-43-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2004/52890; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1060814-91-6, Ethyl 2-(4-bromopyridin-2-yl)acetate, 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: C9H10BrNO2, blongs to pyridine-derivatives compound. Formula: C9H10BrNO2

To a solution of compound 6-7 (2.5 g, 10.24 mmol, 1 eq) and compound 6-10 (2.6 g, 10.24 mmol, 1 eq) in dioxane (40 mL) was added potassium acetate (3.02 g, 30.73 mmol, 3 eq) and Pd(dppf)Cl2.CH2Cl2 (418 mg, 512.12 umol, 0.05 eq). The mixture was degassed under vacuum and purged with nitrogen for three times. The mixture was stirred at 85C for 2 hours under nitrogen atmosphere. TLC (petroleum ether: ether: ethyl acetate = 2:1) showed the starting material was consumed completely and a new spot was formed. The mixture was used directly without work up.

The synthetic route of 1060814-91-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; TRI-INSTITUTIONAL THERAPEUTICS DISCOVERY INSTITUTE, INC.; FUSHIMI, Makoto; SCALTRITI, Maurizio; HELLER, Daniel, Alan; MONTERRUBIO MARTINEZ, Carles; ARRUABARRENA ARISTORENA, Amaia; MEINKE, Peter, T.; FOLEY, Michael, Andrew; ASANO, Yasutomi; ASO, Kazuyoshi; TAKAHAGI, Hiroki; SHAMAY, Yosef; BASELGA TORRES, Jose, Manuel; SASAKI, Yusuke; MICHINO, Mayako; (271 pag.)WO2020/72892; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1122-43-6 ,Some common heterocyclic compound, 1122-43-6, molecular formula is C7H9NO, 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.

Description 143-(2-Fluoro-4-nitrophenoxy)- 14)2,6-Dimethyl-pyridin-3-ol (3.0 g, 24.35 mmol) and cesium carbonate (15.87 g, 48.71 mmol) were added to a solution of 3,4-difluoronitrobenzene (3.87 g, 24.35 mmol) in DMF (30 ml). The mixture was heated at 140 0C for 2 hours. After cooling to room temperature it was filtered through diatomaceous earth and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; 2 % methanol/DCM as eluent) to yield intermediate D14 (5.88 g, 92 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-43-6, its application will become more common.

Reference:
Patent; ORTHO-McNEIL-JANSSEN PHARMACEUTICALS, INC.; ADDEX PHARMA S.A.; WO2009/33702; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem