Day: March 22, 2022

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

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.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

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

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

Application of 846036-96-2, 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. 846036-96-2, name is (4-Amino-6-chloropyridin-3-yl)methanol. A new synthetic method of this compound is introduced below.

To a solution of (4-amino-6-chloro-pyridin-3-yl)-methanol (0.335 g, 2.1 mmol) (from Example 23 supra) in dichloromethane (100 mL) at room temperature was added MnO2 (1.9 g, 21.8 mmol). The reaction mixture was stirred at this temperature for 16 hours then filtered. Solvent was evaporated to give 4-amino-6-chloro-pyridine-3-carbaldehyde as a white solid which was used directly in the next step. (Yield 0.275 g, 83.9%). 1H NMR (300 MHz, CDCl3): delta 9.90 (s, 1H), 8.38 (s, 1H), 6.58 (s, 1H), 1.57 (s, 2H). LC-MS: [M+H]+ 157.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,846036-96-2, (4-Amino-6-chloropyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Luk, Kin-Chun; US2012/184562; (2012); 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. 72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, 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: C6H4ClF3N2

The preparation of 3-amino-2,6-dichloro-5-trifluoromethyl-pyridine from 3-amino-2- chloro-5-trifluoromethyl-pyridine was as follows. A solution of 3-amino-2-chloro-5- trifluoromethyl-pyridine (5 g) (prepared as described in EP 178260, EP 272824) and N- chlorosuccinimide (3.7 g) in acetonitrile (125 ml) was stirred at ambient temperature for 16 hours. The reaction mixture was poured into water, extracted with ethyl acetate, dried over sodium sulfate and then concentrated in vacuo. Chromatography on silica gel (eluent: hexane / ethyl acetate 3:1) afforded 3-amino-2,6-dichloro-5-trifluoromethyl-pyridine (3.5 g): MS (ES+) 231 / 233 / 235 (MH+); IH NMR (400 MHz, CDCl3) 4.34 (s, 2H), 7.35 (s, IH).

With the rapid development of chemical substances, we look forward to future research findings about 72587-18-9.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2009/138219; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 62002-31-7, 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. 62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride. A new synthetic method of this compound is introduced below.

To a mixture of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine dihydrochloride (0.50 g, 2.55 mmol), ethanol (10 mL) and triethylamine (1.10 mL, 7.89 mmol), 2,4-dichlorobenzyl isocyanate (0.52 g, 2.57 mmol) was added. The resulting mixture was stirred at room temperature for 16 h and then concentrated under reduced pressure. The residue was distributed between water (20 mL) and ethyl acetate (75 mL). The organic phase was washed with water (10 mL) and brine (10 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was triturated in diethylether (50 mL) and the crude product was filtered off. Recrystallization from acetone (25 mL) gave 0.30 g (37%) of the title ureaurea as a colourless solid. HPLC (214 nm): elution at 7.97 min. LC-MS: Calcd. for MH+: 325; found: 325. 1H NMR (400 MHz, DMSO-d6): delta2.56 (s, br, 2H), 3.65 (t, J=6 Hz, 2H), 4.29 (d, J=6 Hz, 2H), 4.34 (s, 2H), 7.20 (s, br, 1H), 7.29 (d, J=8 Hz, 1H), 7.39 (dd, J=8, 1 Hz, 1H), 7.47 (s, 1H), 7.56 (d, J=1 Hz, 1H), 11.79 (s, br, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62002-31-7, its application will become more common.

Reference:
Patent; Novo Nordisk A/S; US6908926; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6318-51-0, (4-Chlorophenyl)(pyridin-2-yl)methanone, 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, 6318-51-0, blongs to pyridine-derivatives compound. Recommanded Product: (4-Chlorophenyl)(pyridin-2-yl)methanone

10L glass reactor with mechanical stirring,thermometer,Under nitrogen protection,First with magnesium shavings,p-chlorobenzaldehyde and tetrahydrofuran heated to form a solution,And then dropping 2-cyanopyridine,The reaction to the remaining 2-cyanopyridine remaining,Cooling for post-processing,Add water quench,Adjust pH to about 5,The organic phase was separated and the reaction product was extracted with ethyl acetate,The solvent was concentrated by petroleum ether to obtain the crude product of the first step. The crude product was purified by petroleum ether and ethyl acetate. First add the first step product and 95% ethanol,Add sodium borohydride cooling,The reaction to no raw material for post-treatment,The system is concentrated to dryness,Add water and stir,Suction filtered crude,After ethyl acetate and activated carbon decolorization,Purification with petroleum ether and ethyl acetate gave the pure product of alpha- (4-chlorophenyl) pyridine-2-methanol,The total molar yield was 75% with a purity of 99.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6318-51-0, its application will become more common.

Reference:
Patent; Bengbu Zhong Shi Chemical Co., Ltd.; Yang Qing; Zhao Shimin; Xu Jianxiao; Sun Jiale; (5 pag.)CN106946767; (2017); A;,
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. 1175512-08-9, name is Methyl 5-bromo-4-hydroxynicotinate, molecular formula is C7H6BrNO3, 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. Formula: C7H6BrNO3

Step 1: Methyl 5-bromo-1-isopropyl-4-oxo-1,4-dihydropyridine-3-carboxylate A mixture of methyl 5-bromo-4-oxo-1,4-dihydropyridine-3-carboxylate (151 mg, 0.65 mmol) and Cs2CO3 (420 mg, 1.3 mmol) in DMF (3 mL) was stirred at rt for 15 min and then isopropyl iodide (0.16 mL, 1.6 mmol) was added. The reaction mixture was stirred at rt for 11 days, diluted with EtOAc, filtered through Celite concentrated, and purified via column chromatography (0% to 100% EtOAc in hexanes then 0% to 10% methanol in CH2Cl2) to give the product as an off-white solid (103 mg, 58%). LCMS calcd for C10H13BrNO3 (M+H)+: m/z=274.0. Found: 274.1.

With the rapid development of chemical substances, we look forward to future research findings about 1175512-08-9.

Reference:
Patent; Incyte Corporation; Li, Yun-Long; Wang, Xiaozhao; Barbosa, Joseph; Burns, David M.; Feng, Hao; Glenn, Joseph; He, Chunhong; Huang, Taisheng; Mei, Song; Zhuo, Jincong; (169 pag.)US2017/275290; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem