Category: pyridine-derivatives

Electric Literature of 1122-43-6, 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. 1122-43-6, name is 2,6-Dimethyl-3-hydroxypyridine. A new synthetic method of this compound is introduced below.

Compound 34C (50 mg, 0.14 mmol), potassium carbonate (39 mg, 0.28 mmol), and2,6-dimethylpyridin-3-ol (51 mg, 0.42 mmol) were stirred in DMF (2.5 mL). The reaction was purged with nitrogen, sealed in a vial, and then heated in a microwave reactor at 190C for eight minutes on high absorbance. The crude reaction mixture was concentrated in vacuo, redissolved in DCM, and washed with water. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude reaction mixture was purified using a silica gel cartridge with DCM/methanol (95/5) to provide compound 103 as an off white solid (60 mg, 96%). LCMS: 445.2 (MH’).

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; SCHERING CORPORATION; WO2009/55331; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 22918-01-0, Adding some certain compound to certain chemical reactions, such as: 22918-01-0, name is 2-Bromo-4-chloropyridine,molecular formula is C5H3BrClN, 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 22918-01-0.

Example 103a 2-Bromo-4-chloronicotinaldehyde 103a To a solution of 2-bromo-4-chloropyridine (1.6 g, 8.0 mmol) in anhydrous tetrahydrofuran (40 mL) cooled at -70 C. was added the solution of lithium diisopropyl-amide (5.0 mL, 10.0 mmol, 2.0 M) over a period of 5 minutes and stirred at -70 C. for another 1h. Anhydrous DMF (1.3 g) was introduced over a period of 3 minutes and the mixture was stirred for another 30 minutes. It was then quenched with saturated NH4Cl (30 mL) and extracted with ethyl acetate (20 mL*3). The combined organic layer was dried over anhydrous Mg2SO4, filtered, and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (20:1) to afford 103a as a yellow solid (900 mg, 48%). 1H NMR (500 MHz, DMSO-d6) delta 10.21 (s, 1H), 8.52 (d, J=5.5 Hz, 1H), 7.79 (d, J=5.0 Hz, 1H).

According to the analysis of related databases, 22918-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); 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. 896139-85-8, name is Imidazo[1,2-a]pyridin-7-ol. A new synthetic method of this compound is introduced below., Recommanded Product: Imidazo[1,2-a]pyridin-7-ol

To a solution of intermediate 1 (500 mg, 1 .54 mmol, 1 .0 eq) and Imidazo[l,2-a]pyridin- 7-ol (248.6 mg, 1.85 mmol, 1.2 eq) in THF (20 mL) was added tributylphosphane (624.9 mg, 3.1 mmol, 2.0 eq) and (NE)-N-(piperidine-l-carbonylimino)piperidine-l- carboxamide (779 mg, 3.1 mmol, 2.0 eq) . The mixture was stirred at 15 C for 15 hrs. The solvent was removed. The residue was purified by flash column on silica gel (ISCO; 12 g SepaFlash Silica Flash Column, Eluent from 0% to 3% MeOH / DCM gradient 30 mL/min) and intermediate 78 (240 mg, 33.7% yield) was obtained as a light yellow 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, 896139-85-8, Imidazo[1,2-a]pyridin-7-ol.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WU, Tongfei; BREHMER, Dirk; BEKE, Lijs; BOECKX, An; DIELS, Gaston Stanislas Marcella; LAWSON, Edward Charles; MEERPOEL, Lieven; PANDE, Vineet; PARADE, Marcus Cornelis Bernardus Catharina; SCHEPENS, Wim Bert Griet; SUN, Weimei; THURING, Johannes Wilhelmus John F.; VIELLEVOYE, Marcel; (186 pag.)WO2018/65365; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1138444-17-3, 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 1138444-17-3, name is 6-Bromo-2-chloro-3-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 6-bromo-2-chloro-3-iodopyridine (8.0 g, 25.1 mmol), (E)-2-(2- ethoxyvinyl)-4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolane (4.98 g, 25.1 mmol), cesium carbonate (16.38 g, 50.3 mmol), and [1,1 ?-bis(diphenylphosphino)ferrocene] dichloropalladium(II) (2.052,2.51 mmol) was added 1,4-dioxane (100 mL) and H20 (10 mL). A steady stream of N2 was bubbled through the reaction mixture for 15 minutes then the mixture was heated to 73 C for 20h. The mixture was cooled to ambient temperature, diluted with EtOAc, and washed successively with H20 (2X) and brine (lx). The organic layer was dried over MgSO4, filtered,and concentrated in vacuo. The residue was purified by silica gel column chromatography using a step gradient of 0-10-60% EtOAc/Hexanes as eluent. MS (M+H): 261.

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 1138444-17-3, 6-Bromo-2-chloro-3-iodopyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda, L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/123793; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 185041-05-8, 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.185041-05-8, name is Methyl 2-chloro-4-iodonicotinate, molecular formula is C7H5ClINO2, molecular weight is 297.48, as common compound, the synthetic route is as follows.

2.0 g 2-chloro-4-iodo-nicotinic acid methyl ester (6.7 mmol), (6.7 mmol) and methyl pyrrolidone (NMP) in a mixture of 0.60 g of cuprous cyanide were heated to 10 ml containing N- 130 five hours, after cooling was diluted with 50 ml of ethyl acetate, the mixture was filtered and concentrated under reduced pressure, the residual material was dissolved in 25 ml of ethyl acetate after washing twice with 10 mL of aqueous ammonia, dried over magnesium sulfate and concentrated, the residual material was purified by silica gel column chromatography (moving phase: ethyl acetate: petroleum ether = 3% to 5%), to give the desired product, 2-chloro-nicotinic acid methyl ester cyano, a white solid (1.0 g, 5.1 mmol, 56% yield).

Statistics shows that 185041-05-8 is playing an increasingly important role. we look forward to future research findings about Methyl 2-chloro-4-iodonicotinate.

Reference:
Patent; BIOGEN MA INC.; SUNESIS PHARMACEUTICALS, INC.; ARNDT, JOSEPH; CHAN, TIMOTHY; GUCKIAN, KEVIN; KUMARAVEL, GNANASAMBANDAM; LEE, WEN-CHERNG; LIN, EDWARD YIN-SHIANG; SCOTT, DANIEL; SUN, LIHONG; THOMAS, JERMAINE; VAN VLOTEN, KURT; WANG, DEPING; ZHANG, LEI; ERLANSON, DANIEL; (469 pag.)TWI525093; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 57883-25-7, 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 57883-25-7 as follows.

A suspension of 3-bromo-2-ethoxypyridine (Preparation 1 1 , 28.69 g, 142.0 mmol), bis(pinacolato)diboron (43.3 g, 170.5 mmol), and potassium acetate (41 .8 g, 425.9 mmol) in DMSO (100 mL) was degassed with nitrogen and [1 ,1 ‘- bis(diphenylphosphinoferrocene]dichloro palladium (II) (5.8 g, 7.93 mmol) was added and the reaction mixture was stirred for 6 hours at 95 C. The reaction mixture was filtered through a pad of Arbocel which was washed with ethyl acetate (500 mL). The filtrate was concentrated in vacuo and the crude material was purified by silica gel column chromatography eluting with 50% ethyl acetate in cyclohexane to afford the title compound as a red oil (34.4g, 74%). 1H NMR (400MHz, CDCl3): delta ppm 1 .35 (s, 12H), 1 .39 (m, 3H), 4.37 (m, 2H), 6.81 (m, 1 H), 7.89 (m, 1 H), 8.19 (m, 1 H). LCMS Rt = 3.27 minutes MS m/z 250 [MH]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57883-25-7, its application will become more common.

Reference:
Patent; PFIZER LIMITED; STORER, Robert, Ian; SWAIN, Nigel, Alan; WO2013/93688; (2013); 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. 60290-23-5, name is 1H-Pyrrolo[3,2-c]pyridin-4-amine, molecular formula is C7H7N3, 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. SDS of cas: 60290-23-5

Example 96-Preparation of tert-butyl 4-(bis (tert-butoxycarbonyl) amino)-1H-pyrrolo [3,2-c]pyridine-1-carboxylate (Compound 59) Under nitrogen, compound 58 (1.2 g, 9.02 mmoles) was dissolved in a mixture of acetonitrile (10 mL) and dichloromethane (20 mL) at room temperature. DMAP (4.4 g, 36 mmoles) was added and the mixture was cooled to 0 deg C. After stirring at 0 deg C. for 30 minutes, di-tert-butyl dicarbonate (8.6 mL, 35.7 mmoles) was added. The reaction was stirred at room temperature for 24 hours after which, it was concentrated to dryness. The residue was diluted with ethyl acetate (50 mL) and washed with saturated aqueous potassium bisulfate solution (25 mL). The layers were separated and the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The residue was purified on silica gel (10% ethyl acetate in hexane) giving compound 59 (2.73 g, 70% yield).

With the rapid development of chemical substances, we look forward to future research findings about 60290-23-5.

Reference:
Patent; Levy, Daniel E.; Abarzua, Patricio; (51 pag.)US2017/362235; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 98197-88-7, 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. 98197-88-7, name is 2-(Hydroxymethyl)-4-nitropyridine, molecular formula is C6H6N2O3, 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.

A solution of (4-nitropyridin-2-yl)methanol (100 mg, 0.65 mmol) in ethanol (4 mL) was treated with a solution of sodium ethoxide in ethanol (21% by weight, 0.31 mL, 0.83 mmol) and the reaction mixture was heated under reflux for 48 h. Water (10 mL) was added, the mixturewas neutralized with concentrated aq. hydrochloric acid and ethanol was removed by evaporation in vacuo. More water (20 mL) was added and the mixture was extracted with DCM (4 x 30 mL). Extracts were dried (MgSO4) and concentrated to give (4-ethoxypyridin-2- yl)methanol W (73 mg, 73%) as a red oil, used without purification.LCMS (method A): 2.07 (154.1, MH).

According to the analysis of related databases, 98197-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REDAG CROP PROTECTION LTD; URCH, Christopher John; BUTLIN, Roger, John; CHRISTOU, Stephania; BOOTH, Rebecca, Kathryn; (122 pag.)WO2019/77345; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73101-79-8, 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. 73101-79-8, name is 5-Ethoxy-6-methylpyridin-2-amine, molecular formula is C8H12N2O, 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.

b) The product from part a) (19.0 g) was added dropwise to 5M sodium hydroxide solution (29 ml) and water (100 ml) keeping the temperature below 15 C. This solution was then added quickly to the solution of 5-ethoxy-6-methyl-pyridin-2-amine (20.0 g) in 4M hydrochloric acid (40 ml) and water (200 ml). This mixture was stirred at ambient temperature for 2 hours then filtered to give a solid which was recrystallized from IMS/water to give ethyl 2-(5-ethoxy-6-methylpyridin-2-ylaminomethylene)propionate, m.p. 118-122 C.

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 73101-79-8, 5-Ethoxy-6-methylpyridin-2-amine.

Reference:
Patent; The Boots Company PLC; US5464781; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 639091-75-1, Adding some certain compound to certain chemical reactions, such as: 639091-75-1, name is Methyl 2-(Boc-amino)isonicotinate,molecular formula is C12H16N2O4, 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 639091-75-1.

A 500mL round bottomed flask was charged with methyl 2-((tert-butoxycarbonyl)amino)isonicotinate (5.95 g, 23.6 mmol) and suspended in methanol (1 18 ml). To this stirring solution was added 3.0M potassium hydroxide (23.6 mL, 70.8 mmol). The flask was vented and heated to 50 C for 10 minutes. LCMS analysis showed clean and complete conversion of starting material to a single product consistent with the desired product by mass (m/z=237[M-H]-). The mixture was cooled to room temperature and then 1.ON HCl was added to give a white precipitate. The solid was collected by filtration and dried overnight to give 2-((tert- butoxycarbonyl)amino)isonicotinic acid, HCl (5.2 g, 18.93 mmol, 80 % yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 13.64 (1 H, br. s.), 10.06 (1 H, s), 8.39 (1 H, d, J=5.27 Hz), 8.30 (1 H, s), 7.42 (1 H, dd, J=5.02, 1.51 Hz), 1.48 (9 H, s).

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. 639091-75-1, Methyl 2-(Boc-amino)isonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SCHMITZ, William D.; DEBENEDETTO, Mikkel V.; KIMURA, S. Roy; WO2013/3298; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem