Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 88312-64-5, Methyl 2-amino-5-nitronicotinate, 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, Safety of Methyl 2-amino-5-nitronicotinate, blongs to pyridine-derivatives compound. Safety of Methyl 2-amino-5-nitronicotinate

DMAP (0.744 g, 6.09 mmol, 0.1 equiv) and Boc2O (29.2 g,134 mmol, 2.2 equiv) were successively added portionwise toa suspension of 22 (12.0 g, 60.9 mmol) in freshly distilled THF (200 mL) at room temperature. The solution was stirred at room temperature for 4 h and evaporated in vacuo. The crude product was purified by flash chromatography using PE/DCM/Et3N (86:13:1,v/v/v) to give 23 (22.5 g, 93%) as a colourless solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88312-64-5, Methyl 2-amino-5-nitronicotinate, and friends who are interested can also refer to it.

Reference:
Article; Hedou, Damien; Deau, Emmanuel; Harari, Marine; Sanselme, Morgane; Fruit, Corinne; Besson, Thierry; Tetrahedron; vol. 70; 35; (2014); p. 5541 – 5549;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 116986-09-5, Adding some certain compound to certain chemical reactions, such as: 116986-09-5, name is Methyl 3-(bromomethyl)picolinate,molecular formula is C8H8BrNO2, 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 116986-09-5.

A mixture of 2,6-dihydroxybenzaldehyde (leq) and methyl 3-(bromomethyl)picolinate (leq) was dissolved in anhydrous N,N-Dimethylformamide (DMF). Anhydrous potassium carbonate (K2CO3) ( 1 2eq) was added to this mixture and the reaction was stirred at room temperature for 4 hours. The solvent was then evaporated and the reaction mixture extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and the solvent evaporated. The crude product was purified using SiO2 column chromatography and eluted with the solvent system EtOAc: hexanes = 6: 1 to obtain pure product as pale yellow powder with a yield of 54%. IR (Diamond, cm-1): 3092, 2923, 2851, 1774, 1712, 1632, 1599, 1566, 1515, 1478, 1366, 1276, 1231 , 1 180, 1 136, 1072; 1H-NMR (400 MHz, DMSO-d6): d 1 1.72 (s, 1H), 10.32 (s, 1 H), 8.65 (dd, .7= 4.64, 1.52 Hz, 1H), 8.22 (m, 1 H), 7.66 (dd, J= 7.88, 4.64 Hz, 1 H), 7.54 (t, J= 8.4 Hz, 1H), 6.66 (d, T = 8 Hz, 1H), 6.57 (d, J = 8.4 Hz, 1H), 5.51 (s, 2H), 3.84 (s, 3H), 13C-NMR (100 MHz, DMSO-d6): d 193.59, 166.09, 162.46, 160.68, 148.53, 146.54, 138.72, 136.83, 132.78, 126.44, 1 10.74, 109.79, 103.26, 67.04, 52.35. MS (ESI) m/z found 310.08 (M+Na)+, Calculated 301.2940 [M]+. The purity of the compound was checked by HPLC and was found to be 100% pure.

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. 116986-09-5, Methyl 3-(bromomethyl)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIRGINIA COMMONWEALTH UNIVERSITY; THE CHILDREN’S HOSPITAL OF PHILADELPHIA; SAFO, Martin, K.; ZHANG, Yan; PARAGE, Piyusha, Pradeep; XU, Guoyan; GHATGE, Mohini; VENITZ, Jurgen; ABDULMALIK, Osheiza; (78 pag.)WO2019/182938; (2019); 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.178876-83-0, name is Methyl 6-amino-3-bromopicolinate, molecular formula is C7H7BrN2O2, molecular weight is 231.0467, as common compound, the synthetic route is as follows.Recommanded Product: 178876-83-0

To a 25 mL round bottom flask, were added methyl 6-amino-3-bromopicolinate (1 g, 0.0043 mol), 3-fluorophenylboronic acid (0.72 g, 0.0052 mol), potassium carbonate (1.52 g, 0.011 mol), 1,4-dioxane (20 mL) and water (4 mL). The reaction mixture was degassed with nitrogen for 5 min. To the same flask, bis(triphenylphosphine)palladium(II) dichloride (0.14 g, 0.00022 mol) was added. The reaction mixture was again degassed with nitrogen for 5 min. The reaction mixture was stirred at 90 C for 2 h. The volatiles were evaporated under reduced pressure to get the residue. The residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to get the crude product. The crude product was purified by flash column chromatography using 20 – 40 % ethyl acetate in hexane to obtain the title compound [0.6 g, 57 %]. FontWeight=”Bold” FontSize=”10″ H NMR (CDC13, 400 MHz): delta 7.68-7.63 (m, 1H), 7.48 (d, = 8.8 Hz, 1H), 7.36-7.31 (m, 1H), 7.05-6.97 (m, 2H), 6.67 (d, = Hz, 1H), 4.79 (brs, 2H), 3.72 (s, 3H); LC-MS: 247.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,178876-83-0, Methyl 6-amino-3-bromopicolinate, and friends who are interested can also refer to it.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BEJUGAM, Mallesham; HOSAHALLI, Subramanya; MAHALINGAM, Natarajan; WO2014/125426; (2014); 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 72716-80-4, name is 5,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

To a suspension of 5,6-dimethyl-2-oxo-l,2-dihydropyridine-3-carbonitrile (5.90 g) in Eta2O(145 ?iL) was added cone. HCl (145 mL) dropwise and the mixture was stirred at ambient temperature for 15 min and at reflux for 60.5 h and concentrated under reduced pressure. The residue was suspended with CHCl3 (150 mL) and MeOH (7.5 mL) and the mixture was heated at 65 0C on a water bath and filtered. The insoluble material was suspended in CHCl3 (100 mL) and MeOH (5 mL) and the mixture was heated at 65 0C on a water bath and filtered. The combined filtrate was concentrated under reduced pressure. To the residue were added MeOH (75 mL) and K2CO3 (5 g) and the mixture was stirred at ambient temperature for 30 min. The insoluble material was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in CHCl3 (100 mL) and the insoluble material was filtered. The filtrate was concentrated under reduced pressure to give 5,6- dimethylpyridin-2(lH)-one (2.19 g) as a yellow solid.1HNMR (300 MHz, CDCl3, delta): 2.05 (s, 3H), 2.31 (s, 3H), 6.38 (d, J= 9.2 Hz, IH), 7.26 (d, J= 9.2Hz, IH); ESI MS m/z 124 (M+H-I, 100%).

With the rapid development of chemical substances, we look forward to future research findings about 72716-80-4.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; ARENA PHARMACEUTICALS, INC.; WO2006/35967; (2006); 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.52605-96-6, name is 2-Chloro-3-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.57, as common compound, the synthetic route is as follows.Computed Properties of C6H6ClNO

A three-necked flask was charged with Compound 1 (5.58 g, 39.0 mmol), N, N-dimethylformamide (60 mL) and sodium methoxide (6.20 g, 115.0 mmol); the reaction was stirred overnight at 60 C.The reaction was cooled to room temperature, water (120 mL) was added and extracted with ethyl acetate (80 mL x 3); the organic phases were combined, washed with water (100 mL x 2) and saturated brine (100 mL), dried over sodium sulfate, . The filtrate was spin-dried to give a yellow liquid, compound 2 (4.0 g, 28.9 mmol, 74%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52605-96-6, 2-Chloro-3-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Kanghua (Shanghai) Drug Discovery Co., Ltd.; Ma Jingxiang; (5 pag.)CN107286084; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 936342-91-5, 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. 936342-91-5, name is 5-Bromo-2-(chloromethyl)pyridine hydrochloride, molecular formula is C6H6BrCl2N, 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 mixture of 5-bromo-2-methylpyridine (500mg, 2.06mmol) and 1-methanesulfonyl-piperazine (440mg, 2.68mmol) was dissolved in N, N- dimethylformamide (10ml) was then added carbonate potassium (996mg, 7.21mmol), the reaction was stirred for 12 hours at room temperature, 100ml of water was added to the reaction mixture was cooled, (100ml * 3) and extracted with ethyl acetate, then with saturated sodium chloride solution (100ml * 2) and washed to give the organic phase was dried over anhydrous magnesium sulfate filtered, and concentrated under reduced pressure to give 1- (5-bromo – 2-methyl-pyridin) yl-4-methanesulfonyl – piperazine (520mg, white solid), yield: 75.6percent.

According to the analysis of related databases, 936342-91-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHANGHAI CDYMAX PHARMACEUTICALS CO., LTD; An, Xiaoxia; Bie, Pingyan; Liu, Jun; Yang, Wuli; (42 pag.)CN103360407; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 55404-31-4 , The common heterocyclic compound, 55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine, molecular formula is C6H5BrClN, 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.

Step 3: In a sealed tube, NaOMe (25% in MeOH, 3.1 mL, 13 mmol) was added to a solution of compound 94 (1.8 g, 8.7 mmol) in MeOH (17 mL). The reaction was heated at 75 C for 3 days. The reaction mixture was cooled to room temperature, diluted with EtOAc, washed with saturated NH4CI and brine, dried over MgS04, filtered and concentrated. The crude product was purified by flash chromatography over silica gel, which was eluted with heptanes/EtOAc (0-15%) to afford compound 95 as a clear oil (991 mg, 56% yield). 1H NMR (400 MHz, DMSO-c/6) delta 8.00 (d, J = 5.0 Hz, 1 H), 6.98 (d, J = 4.8 Hz, 1 H), 3.90 (s, 3 H), 2.35 (s, 3 H).

The synthetic route of 55404-31-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); 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.76005-99-7, name is 2-Methoxy-4-methylpyridin-3-amine, molecular formula is C7H10N2O, molecular weight is 138.1671, as common compound, the synthetic route is as follows.Recommanded Product: 2-Methoxy-4-methylpyridin-3-amine

(2) 29.4 g of Compound 2 was dissolved in 600 mL of DCM in a 2 L three-necked flask, and 25.0 g of AcOK potassium acetate was added at 0 C., and 43.4 g of Ac2O; about 40min drops completed, adding 11.25g18-crown ether, maintaining the temperature 0 C, 54.9g of isoamyl nitrite is dripped, about 40min drops completed, the natural return to room temperature.After the system has returned to room temperature, it is heated to 65 degrees reflux overnight (about 12 hours).The next day the TLC test material disappeared, NaHCO3The saturated solution was adjusted to pH = 6, the organic phase was separated, the aqueous phase was extracted once with DCM, the organic phases were combined and dried to dryness, then K2CO3The residue was spin-dried with methanol for about 1 h, filtered and spun dry. The dried residue was then treated with EA and saturated brine. The organic phase was dried to give compound 3 (crude) 29 g, 91.3% yield, which was used directly in Next step.TLC information: Raw Rf = 0.8, Product Rf = 0.5.Developing agent: PE: EA = 1: 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76005-99-7, 2-Methoxy-4-methylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Si Fenke Si Pharmaceutical Research And Development (Tianjin) Co., Ltd.; Yao Qingjia; Wu Simin; Xu Yangjun; (7 pag.)CN104230811; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 955372-86-8, Adding some certain compound to certain chemical reactions, such as: 955372-86-8, name is 3-Bromo-5-fluoroisonicotinic acid,molecular formula is C6H3BrFNO2, 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 955372-86-8.

A mixture of 3-bromo-5-fluoroisonicotinic acid (5a, 1 .87 g, 8.5 mmol) and HATU (4.85 g, 12.75 mmol) in DMF (30 ml) was added DIEA (4.5 ml), the mixture was stirred at r.t for 20 minutes, then isonicotinimidamide (1 .236 g, 10.2 mmol) was added. Stirring was continued for another 15 hours at r.t. The reaction mixture was concentrated under reduced pressure. The light brown syrup crude mixture was then dissolved in DCM and purified by silica gel chromatography (eluted with 0-10% MeOH/solvent A, solvent A is mixture of 4 liter DCM and 8 ml of 7N ammonia solution in MeOH), fractions 66-80 were pooled and concentrated to afford the desired product 3-bromo-5-fluoro-N-(imino(pyridin-4- yl)methyl)isonicotinamide 5b (566 mg, 20.6%). 1 H NMR (500 MHz, DMSO-d6) delta 10.27 (s, 1 H), 10.09 (s, 1 H), 8.79 – 8.73 (m, 2H), 8.71 (s, 2H), 7.95 – 7.89 (m, 2H). LCMS (m/z [M+H]+): 323.0.

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. 955372-86-8, 3-Bromo-5-fluoroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BEHNKE, Dirk; BERENSHTEYN, Frada; HAO, Xueshi; HOFFMAN, Timothy; JIN, Qihui; LACOSTE, Arnaud; LEE, Cameron; LIU, Jun; LIU, Yahu; MAIBAUM, Juergen Klaus; MO, Tingting; PAN, Jianfeng; QU, Xin; TCHORZ, Jan; XIE, Yun Feng; YAN, Shanshan; ZOU, Yefen; (564 pag.)WO2018/198077; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine, 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, SDS of cas: 92276-38-5, blongs to pyridine-derivatives compound. SDS of cas: 92276-38-5

To a stirred solution of 6-bromo-1H-i,2,3-triazolo[4,5-b]pyridine (250 mg, 1.26 mmol) in DMF (5 mL) at rt was added 60% sodium hydride in mineral oil (55 mg, 1.38 mmol) and the mixture was stirred at rt for 30 mins. (2-(Chloromethoxy)ethyl)trimethylsilane (419 mg, 2.51 mmol) was added and the mixture was stirred for 15 h. The reaction mixture was partitioned between water and EtOAc and the aqueous layer was separated and further extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0 – 20% EtOAc in hexanes to afford a 1:1 mixture of 6-bromo- 1 -((2- (trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5-b]pyridine and 6-bromo-3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo[4,5 -b]pyridine (240 mg) as an oil, which was not purified further. LC-MS (ESI) mlz 329 and 331 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; HOLLADAY, Mark, W.; LIU, Gang; ROWBOTTOM, Martin, W.; WO2015/31613; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem