Day: April 19, 2022

Electric Literature of 1231930-13-4 , The common heterocyclic compound, 1231930-13-4, name is 3-Bromo-2-methyl-6-nitropyridine, molecular formula is C6H5BrN2O2, 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 mixture of Example C7 (1.185 g, 3.93 mmol), Example A6 (0.746 g, 2.81 mmol), K2CO3 (1.165 g, 8.43 mmol) and Pd(PPh3)4 (0.325 g, 0.281 mmol) in dioxane (11 mL) and water (3 mL) was sparged with Ar and heated at 90 C. overnight. The mixture was cooled to RT, treated with EtOAc and brine and the solids removed via filtration through diatomaceous earth. The layers of the filtrate were separated, the aqueous layer extracted with additional EtOAc (3*) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 2-methyl-3-((2-(4-(1-methylpiperidin-4-yl)phenyl)pyridin-4-yl)oxy)-6-nitropyridine (553 mg, 49%). MS (ESI) m/z: 405.2 (M+H+).

The synthetic route of 1231930-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Samarakoon, Thiwanka; Caldwell, Timothy Malcolm; Vogeti, Lakshminarayana; Ahn, YuMi; Patt, William C.; Yates, Karen M.; US2014/315917; (2014); 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.3678-63-5, name is 4-Chloro-2-picoline, molecular formula is C6H6ClN, molecular weight is 127.57, as common compound, the synthetic route is as follows.name: 4-Chloro-2-picoline

Manufacturing Example 51-1-1 (4-Chloro-pyridin-2-yl)-methanol; To a mixture of 4-chloro-2-picoline (1.0 g, 7.84 mmol) and dichloromethane (20 mL), was added m-chloroperbenzoic acid (3.5 g, 13.2 mmol) on an ice bath, which was stirred for 1.5 hours at room temperature. Water and sodium hydrogencarbonate were added to the reaction, followed by extraction with dichloromethane. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. Acetic anhydride (20 mL) was added to the residue obtained by concentrating the filtrate under a reduced pressure, and this was stirred for 1 hour at 100 C. The reaction mixture was cooled to room temperature and concentrated under a reduced pressure. A 5 N aqueous sodium hydroxide solution (1.57 mL, 7.87 mmol) was added to a mixture of the resulting residue and methanol (20 mL) on an ice bath, which was stirred for 1.5 hours at room temperature. Water was added to the mixture, which was then extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=6:1) to obtain the title compound (200 mg, 18%).1H-NMR Spectrum (CDCl3) delta (ppm): 4.76 (2H, s), 7.23-7.25 (1H, m), 7.32-7.33 (1H, m), 8.46 (1H, d, J=5.6 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3678-63-5, 4-Chloro-2-picoline, and friends who are interested can also refer to it.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); 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.851607-27-7, name is 5-Bromo-4-chloro-2-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-4-chloro-2-methoxypyridine

To a solution of cyclopropylmethanol (446 mg, 6.18 mmol) in THF (10 mL) was added NaH (247 mg, 6.18 mmol, 60% in mineral oil) in one portion at 0 C. The reaction mixture was warmed up to 20 C. over a period of 30 mins and stirred at 20 C. for 10 mins. Then 5-bromo-4-chloro-2-methoxypyridine (550 mg, 2.47 mmol) was added in one portion and the mixture was stirred at 70 C. for 4 hours. The mixture was diluted with saturated ammonium aqueous solution (50 mL) and extracted by EtOAc (2*30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to give the crude product which was purified by silica gel column chromatography (PE:EA=20:1 to 10:1) to afford the title compound (450 mg, 70.6%) as colorless oil. 1H NMR: (CDCl3, 400 MHz) delta: 8.11 (s, 1H), 6.18 (s, 1H), 3.90 (s, 3H), 3.89-3.88 (m, 2H), 1.39-1.27 (m, 1H), 0.70-0.67 (m, 2H), 0.46-0.43 (m, 2H). LCMS (M+H)+=258.0 (M+1)+; 260.0

At the same time, in my other blogs, there are other synthetic methods of this type of compound,851607-27-7, 5-Bromo-4-chloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Bennett, Michael John; Betancort, Juan Manuel; Boloor, Amogh; Kaldor, Stephen W.; Stafford, Jeffrey Alan; Veal, James Marvin; US2015/111885; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13296-04-3 ,Some common heterocyclic compound, 13296-04-3, molecular formula is C11H10N2, 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.

EXAMPLE 159; A mixture of EXAMPLE 153 (69.2 rag), 4~pyridin-4-ylphenylamine (37.8 mg), palladium (II) acetate (3.0 mg), 4s5-bis(diphenylphosphiiio)-9,9-dirnethylxanthene (9.6 mg), cesium carbonate (141.6 mg) and dioxane (2.5 ml) were heated in a microwave at 16O0C for 40 minutes. The solvent was removed and the residue purified by flash chromatography using 20: 1 dichloromethane/methanol. Further purification by reverse phase HPLC afforded the title compound (12.8 mg, 13%). 1H NMR (DMSOd6) delta 10.40 (s, IH), 9.84 (s, IH), 8.81 (d, J=6.8 Hz, 2H), 8.38 (d, J=5.8 Hz, IH), 8.24 (d, J=6.8 Hz, 2H), 7.94-8,04 (m, 5H), 734 (d, J=5.8 Hz, IH)1 1..55-1 .75 (m, 6H), 1.27-1.36 (m, 2H), 1.17 (d, J=6.8 Hz, 3H), 0.87-1.12 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13296-04-3, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2007/140233; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 929617-30-1, name is 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine. A new synthetic method of this compound is introduced below., Product Details of 929617-30-1

Into a 30 mL sealed tube was placed 5-bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine (900 mg, 4.24 mmol), Pd(dppf)CI2 (315 mg, 0.43 mmol), KOAc (1.25 g, 12.7 mmol) and N,N- dimethylformamide (10 mL). This was followed by the addition of methanol (10 mL) and CO gas. The solution was stirred for 1 h overnight at 80C in an oil bath. The mixture was concentrated under vacuum. The residue was purified over a silica gel column with dichloromethane/methanol (20:1). This resulted in 0.60 g (74%) of methyl 3-methyl-1H- pyrazolo[3,4-c]pyridine-5-carboxylate as a brown solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 929617-30-1, 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LTD.; SCHIEMANN, Kai; MALLINGER, Aurelie; (147 pag.)WO2016/26549; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 100848-70-2, 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. 100848-70-2, name is 2-Methoxy-4-methylpyridine, molecular formula is C7H9NO, 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.

Ammonia was condensed into a round bottomed flask. While cooling the liquid ammonia with a CO2/acetonebath, NaNH2 (1.73 g) was added quickly. Then, 2-methoxy-4-methylpyridine (5.02 g) was added slowly via a syringe inthe course of 5 min. The reaction mixture turned yellow immediately, but the starting material seemed to precipitate.The cooling bath was removed, and after 20 min, the reaction mixture had turned deep brown. The cooling bath wasput in place again, and sodium 2-chloroacetate (4.74 g) was added portionwise in the course of 5 min. After stirring for35 min, the cooling bath was removed; the reaction mixture had solidified partly. 50 min later, the reaction mixture wasstirring again, and after another 40 min, NH4Cl (3.29 g) was added carefully. The turbid, light brown reaction mixtureimmediately turned clear and yellow. The mixture was left stirring at RT overnight to allow the ammonia to evaporate.To the pasty residue, water (50 ml) was added to give a turbid, yellowish mixture. The pH of the mixture was adjustedto ?4 using 3M aqueous HCl; at first, a white precipitate formed, followed by dark grey lumps. The mixture was extractedwith DCM (2 x 50 mL), the combined extract was washed with brine (50 ml), dried over sodium sulfate, and concentratedin vacuo. The residue was taken up with 1M aqueous NaOH (50 ml), and washed with diethyl ether (50 ml). The basicaqueous layer was adjusted to pH ?4-5 using 3M HCl (aq), and extracted with DCM (2 x 25 ml). Then, the pH wasadjusted to pH ?3-4, and the aqueous layer was extracted again with DCM (2 x 25 ml). The combined organic layer wasdried over sodium sulfate, and concentrated in vacuo

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 100848-70-2, 2-Methoxy-4-methylpyridine.

Reference:
Patent; Dr. August Wolff GmbH & Co. KG Arzneimittel; GERTSCH, Juerg; EP2435019; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1256791-13-5, 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. 1256791-13-5, name is 1-(6-Chloro-5-methylpyridin-3-yl)ethanone, molecular formula is C8H8ClNO, 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 mixture of compound l-(6-chloro-5-methyl-3-pyridyl)ethanone (850 mg), compound l-(3,5- dichloro-phenyl)-2,2,2-trifluoro-ethanone (1.82 g) and K2C03 (862mg) in 20 ml of dichloroethane was added Et3N (50 mg). The mixture was refluxed for 16 h. After cooling to 0C, Bu4N+Br” (322 mg), NH2OH.HCl (690 mg, 10 mmol) and NaOH (800 mg, 4 N) was added and the reaction mixture was stirred at room temperature for 16 h. Then, the reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate three times. The combined organic layers were dried over MgS04 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give the title compound (1.6 g). lU NMR (300Mz, DMSO-d6): delta 2.39 (s, 3H), 4.37 (d, 1H), 4.43 (d, 1H), 7.62 (s, 2H), 7.83 (s, 1H), 8.17 (s, 1H), 8.55 (s, 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 1256791-13-5, 1-(6-Chloro-5-methylpyridin-3-yl)ethanone.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; CASSAYRE, Jerome Yves; EL QACEMI, Myriem; LUKSCH, Torsten; RENOLD, Peter; WO2012/156400; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1083057-12-8 , The common heterocyclic compound, 1083057-12-8, name is tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, molecular formula is C17H19NO2, 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.

13 g of tert-butyl-3(3-methylpyridin-2-yl)benzoate was dissolved in 80 ml ethyl acetate, then 4 ml water and 15 g ureahydrogen peroxide were added. 22 g of phthalic anhydride was added portion wise and the reaction temperature was maintained below 45 C. Thereaction mixture was heated to 45 C and stined for 4 hours. After completion of reaction, the reaction mass was cooled to room temperature. 100 ml of 10% sodium sulphite solution was added slowly and the reaction mixture was stined for 30 minutes. The layers were separated and organic layer was washed with 100 ml 10% sodium carbonate and 100 ml 10% sodium chloride solution. The organic phase is then filteredand concentrated under vacuum to afford 2-(3-(tert-butoxycarbonyl)phenyl)-3- methylpyridine-1-oxide (13 g, 94.8 %).

The synthetic route of 1083057-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MYLAN LABORATORIES LIMITED; ATTANTI, Veera Venkata Srinivasa Rao; TUMMALAPALLI, Umasankara Sastry; POTLA, Murali Krishna; TALATALA, Appireddy; GOSULA, Veera Venkata Satya Surya Appala Narasimha Tataji; KOMMARAJU, Srinivas; (45 pag.)WO2017/17696; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 24484-98-8, 4-Chloropyridine-2,3-diamine, 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: C5H6ClN3, blongs to pyridine-derivatives compound. COA of Formula: C5H6ClN3

Intermediate 8 (700mg, 4.876 mmol), polyphosphoric acid (5 g) and HOAc (442 mg, 7.31 mmol) are heated at 1500C for one hour. The reaction is dissolved in water, then NaOH is added until the pH is adjusted to pH=13. The solution is extracted with ethyl acetate (2×150 mL), washed with K2CO3 solution and brine, dried, and evaporated to give crude 7-chloro-2-methyl- 3H-imidazo[4,5-b]pyridine (9), which is used without purification. 1H NMR 400 MHz (CDCl3) delta 8.14 (s, IH), 6.55 (m, 2H), 2.69 (s, 3H); MS m/z 168.00 (M + 1).

The synthetic route of 24484-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2008/144253; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 944937-30-8, name is Methyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, molecular formula is C9H7IN2O2, 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. HPLC of Formula: C9H7IN2O2

Step 2. 1-tert-butyl 5-methyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-1,5-dicarboxylate To a mixture of methyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (700 mg, 2.32 mmol) in dichloromethane (10 mL) and tetrahydrofuran (10 mL) was added N,N-diisopropylethylamine (1.21 mL, 6.95 mmol), di-tert-butyldicarbonate (607 mg, 2.78 mmol), and 4-dimethylaminopyridine (28 mg, 23 mmol). The reaction was allowed to stir at room temperature for 16 hours. The reaction was concentrated and purification by flash column chromatography (0-50% ethyl acetate/heptanes) gave the title compound (760 mg, 82%) as a solid. +APCI (M+H) 403.3; 1H NMR (400 MHz, DMSO-d6, delta): 8.93 (d, J=2.0 Hz, 1H), 8.16 (d, J=2.0 Hz, 1H), 8.14 (s, 1H), 3.91 (s, 3H), 1.59 (s, 9H).

With the rapid development of chemical substances, we look forward to future research findings about 944937-30-8.

Reference:
Patent; PFIZER INC.; US2012/270893; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem