Category: pyridine-derivatives

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. 71670-70-7, name is 2-(Chloromethyl)-5-methylpyridine hydrochloride, molecular formula is C7H9Cl2N, 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. Computed Properties of C7H9Cl2N

Intermediate K: 2-((3-Chloro-5-fluoro-4-nitrophenoxy)methyl)-5-methylpyridine To a mixture of 3-chloro-5-fluoro-4-nitrophenol (2.6 g, 13 mmol), cesium carbonate (8.7 g, 27 mmol), and 2-(chloromethyl)-5-methylpyridine hydrochloride (2.4 g, 13 mmol) was added DMF (88 mL) and the resulting mixture was heated to 75 Celsius for 19 h. The mixture was cooled to RT and then stirred for an additional 20 h. The resulting mixture was then partitioned between sat. NaHCO3 and EtOAc. The organic layer was separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated to dryness. The resulting residue was purified using FCC to afford the title compound (2.93 g, 74%). MS (ESI): mass calcd. for C13H10ClFN2O3, 296.04; m/z found, 297.1 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.45 (dd, J=1.4, 0.7, 1H), 7.55 (dd, J=7.9, 1.6, 1H), 7.32 (d, J=7.9, 1H), 6.93 (dd, J=2.5, 1.8, 1H), 6.79 (dd, J=11.1, 2.6, 1H), 5.19 (s, 2H), 2.37 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 71670-70-7.

Reference:
Patent; Chai, Wenying; Dvorak, Curt A.; Eccles, Wendy; Edwards, James P.; Goldberg, Steven D.; Krawczuk, Paul J.; Lebsack, Alec D.; Liu, Jing; Pippel, Daniel J.; Sales, Zachary S.; Tanis, Virginia M.; Tichenor, Mark S.; Wiener, John J. M.; US2014/275029; (2014); 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. 175204-82-7, name is Methyl 4-(trifluoromethyl)nicotinate, molecular formula is C8H6F3NO2, 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. Quality Control of Methyl 4-(trifluoromethyl)nicotinate

REFERENCE EXAMPLE 46 Production of (4-trifluoromethylpyridin-3-yl)-methanol; A solution of 0.37 g (9.7 mmoles) of lithium aluminum hydride dissolved in 100 ml of THF was cooled to -50 C. Thereto was gradually added dropwise a solution of 2.0 g (9.8 mmoles) of methyl 4-trifluoromethylnicotinate dissolved in 30 ml of THF. The mixture was stirred at -50 C. for 3 hours to give rise to a reaction. After confirmation of the completion of the reaction, ethyl acetate was added, followed by stirring for a while. Water was added, followed by stirring for a while. The reaction mixture was filtered under vacuum. The filtrate was extracted with ethyl acetate. The resulting organic layer was washed with water and an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 0.6 g (yield: 35.3%) of (4-trifluoromethylpyridin-3-yl)-methanol as a yellow oily substance. 1H-NMR [CDCl3/TMS, delta (ppm)]: 9.00 (1H,s), 8.73 (1H,d), 7.51 (1H,d), 4.95 (2H,s)

With the rapid development of chemical substances, we look forward to future research findings about 175204-82-7.

Reference:
Patent; Takahashi, Satoru; Ueno, Ryohei; Yamaji, Yoshihiro; Fujinami, Makoto; US2005/256004; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 4966-90-9, 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.4966-90-9, name is 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one, molecular formula is C6H6N2O4, molecular weight is 170.12, as common compound, the synthetic route is as follows.

Phosphorus oxychloride (500 ml) and 2,4-dihydroxy-6-methyl-3-nitropyridine (50.0 g) were combined and heated at 90 C. for 16 hours. The reaction mixture was cooled and the phosphorus oxychloride was removed under reduced pressure. The resulting black oil was dissolved in diethyl ether and water (2 L) (added with care). The aqueous layer was separated, made basic with sodium carbonate, and washed with diethyl ether (51 L). The combined organic layers were dried with magnesium sulfate and concentrated under reduced pressure. The resulting black needles were extracted with hot heptane. The hot heptane solution was filtered, and the heptane was removed to produce light brown needles (46.71 g), which were pure by NMR analysis. Example 3 [0162] Part A [0163] 2,4-Dichloro-6-methyl-3-nitropyridine [0164] Phosphorus oxychloride (2000 ml) and 2,4-dihydroxy-6-methyl-3-nitropyridine (200.0 g) were combined in a flask equipped with a 20% sodium hydroxide scrubber and heated with mixing at 80 C. for 16 hours. HPLC monitoring indicted that the reaction was complete. The black reaction mixture was cooled to room temperature, and the phosphorus oxychloride was removed under reduced pressure. The resulting black oil was slowly poured into water (1500 ml) with stirring, while not exceeding a temperature of 60 C. After cooling overnight, the resulting aqueous mixture was washed with chloroform (5×1L). The organic layers were combined, dried with magnesium sulfate, and concentrated under reduced pressure to a brown oil. The oil was dissolved in ethyl acetate (1L), and the resulting solution was washed with a 20% aqueous sodium carbonate solution (500 ml). A white solid formed and was filtered off. The filtrate was dried with magnesium sulfate and concentrated under reduced pressure to a brown solid. The solid was recrystallized from n-heptane (400 ml) to produce light brown crystals (175 g), which were used in the next step.

Statistics shows that 4966-90-9 is playing an increasingly important role. we look forward to future research findings about 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one.

Reference:
Patent; 3M Innovative Properties Company; US2003/232852; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 36357-38-7, 5-Acetyl-2-methylpyridine, 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, 36357-38-7, blongs to pyridine-derivatives compound. Computed Properties of C8H9NO

To a stirring solution of 1-(6-methyl-3-pyridinyl)ethanone (1.0 g, 7.4 mmol) in absolute ethanol (10 ml) at 0 0C was added sodium borohydride (0.14 g, 3.7 mmol) portionwise over 20 minutes. The reaction mixture was stirred at 0 0C for 1.5 hours before warming to room temperature. The mixture was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate. The organic phase was dried over sodium sulphate, filtered, and evaporated in vacuo to give the crude product 1-(6-methyl-3- pyridinyl) ethanol (810 mg).1H-NMR (400MHz, CDCI3): delta 8.45 (1 H, s), 7.63 (1 H, m), 7.14 (1 H, d, J=8Hz), 4.93 (1 H, m), 2.54 (3H, s), 2.09 (1 H, bs), 1.53 (3H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,36357-38-7, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/80637; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 75073-11-9, 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.75073-11-9, name is 5-Iodo-6-methylpyridin-2-amine, molecular formula is C6H7IN2, molecular weight is 234.04, as common compound, the synthetic route is as follows.

PREPARATION 3 Diethyl 2-{[(5-iodo-6-methyl-2-pyridinyl)amino]methylene}malonate A solution of 2-amino-5-iodo-6-picoline (Prep 2 4.48 g) and diethyl ethoxymethylenemalonate (4.25 mL) is heated at 95 C. for 1.5 h. The reaction is cooled to room temperature. Hexanes (20 mL) are added and the resulting solid is filtered, washed with a minimal amount of hexanes, and dried to give the desired enamine (6.45 g, 83%). Physical Characteristics are as follows: m.p. 138-139 C.; 1H NMR (300 MHz, DMSO-d6) delta 10.70, 8.96, 8.11, 7.03, 4.21, 4.14, 1.26, 1.24; IR (drift) 2989, 1686, 1641, 1603, 1568, 1548, 1421, 1373, 1363, 1333, 1272, 1251, 1232, 1211, 800 cm-1; MS (ESI) m/z 404.9 (M+H)+, 402.9 (M-H)-; Anal. Calcd for C14H17IN2O4: C, 41.60; H, 4.24; N, 6.93; Found: C, 41.68; H, 4.35; N, 6.83.

Statistics shows that 75073-11-9 is playing an increasingly important role. we look forward to future research findings about 5-Iodo-6-methylpyridin-2-amine.

Reference:
Patent; Vaillancourt, Valerie A.; US2002/7066; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 40473-07-2 ,Some common heterocyclic compound, 40473-07-2, molecular formula is C6H6BrNO, 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.

To a stirred solution of 2-bromo-6-methoxypyridine (10 g, 0.053 mol) in dry ACN (100 ml_), was added A/-bromosuccinimide (18.82 g, 0.106 mol) at RT. The reaction mixture was stirred at 90? for 16 h. The completion of reaction was monitored by TLC. After completion, the reaction was filtered through a celite bed, diluted with water (30 mL) and exacted with 10% EtOAc in petroleum ether (2 x 100 mL). The combined organic layer washed with water (10 mL), brine (10mL) dried over Na2SC>4 and concentrated. The resulting crude material was purified by crystallization (5 mL DCM in 50 mL n- pentane). The solid was filtered, washed with n-pentane and then dried unber vacuum to get afford the tittle compound. Yield: 35% (4.92 g, off white solid). 1H NMR (400 MHz, CDCI3): d 7.70 (d, J = 8.4 Hz, 1 H), 6.62 (d, J = 8.4 Hz, 1 H), 3.93 (s, 3H), LCMS: (Method A) 367.9 (M+H), Rt. 2.4 min, 96.7% (Max).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,40473-07-2, its application will become more common.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; WISHART, Grant; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; RAKESH, Paul; (250 pag.)WO2020/39028; (2020); 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.23056-46-4, name is 2-Bromo-5-methyl-3-nitropyridine, molecular formula is C6H5BrN2O2, molecular weight is 217.02, as common compound, the synthetic route is as follows.Product Details of 23056-46-4

[00259] A round bottom flask was charged with 2-bromo-5-methyl-3- nitropyridine (60.53 g, 278.9 mmol) and CuCN (27.52 g, 307.3 mmol) The flask was evacuated, and back-filled with nitrogen. DMF (150 mL) was added via cannula. The solution was heated to 70 0C for 1.5 hours. After cooling to room temperature, the reaction mixture was poured into EtOAc (500 mL) and water (250 mL). Both phases were filtered through a 1 cm bed of celite. The layers were separated, and the organic phase washed with water (2 * 100 mL) then with a solution of 1 :1 sat. aq. NH4CI / NH4OH (2 x 100 mL). The combined aqueous layers were extracted with EtOAc (2 * 200 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound (36.1Og, 79% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23056-46-4, 2-Bromo-5-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2009/9740; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1196152-34-7, 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 1196152-34-7, name is 2-Bromo-6-methoxypyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

(S)-2-Hydroxy-2,4-dimethylpentanoic acid (3073 g; 21 mol; 1.00 eq.), 4-dimethylaminopyridine (128 g; 1 mol; 0.05 eq.) and dichloromethane (24.5 L) are placed in a 100 L reactor. The reaction mixture is cooled to about 0 C. Pyridine (3.75 L) and dichloromethane (6 L) are added while maintaining the temperature at 0-5 C. (0238) Trimethylchlorosilane (5.8 L; 46 mol; 2.20 eq.) is added while maintaining the temperature below 5 C. The reaction mixture is warmed to 20 C. and stirred for 4 hours 30 minutes at this temperature, and then cooled to 0 C. N,N-Dimethylformamide (55 ml; 0.71 mol; 0.03 eq.) is added while maintaining the temperature below 5 C., and oxalyl chloride (1622 ml; 18.9 mol; 0.90 eq.) is then added while maintaining the temperature below 5 C. The reaction mixture is stirred for 1 hour at this temperature and N,N-dimethylformamide (27.50 ml; 0.36 mol; 0.02 eq.) is then added. The reaction mixture is warmed to about 20 C. and stirred for 1 hour at this temperature. (0239) A solution of 2-bromo-4-amino-6-methoxypyridine (3543 g; 17.4 mol; 0.83 eq.) in a dichloromethane (27.3 L)/pyridine (1.9 L) mixture is added to the preceding solution while maintaining the temperature below 25 C. The reaction mixture is stirred for 30 minutes at this temperature. The reaction progress is monitored by TLC with 5% control. (0240) A solution of acetic acid (23 L; 41 mol; 1.95 eq.) in ethanol (19 L) is prepared in a new disposable container of suitable volume and then poured into the reaction mixture while maintaining the temperature below 25 C. The reaction medium is stirred overnight at about 20 C. The reaction progress is monitored by TLC. (0241) An aqueous solution of hydrochloric acid (2.4 L; 12.00 M; 28.77 mol; 0.78 V) in water (27 L) is prepared in a new disposable container of suitable volume and then poured into the reaction medium and stirred for 10 minutes. The aqueous phase is discarded and the organic phase is then washed with water (30 L). The aqueous phase is discarded and the organic phase is then washed again with a solution prepared from NaOH (1 177.29 g; 29.43 mol; 1.40 eq.) in water (30 L). The aqueous phase is discarded and the organic phase is then washed again with water (30 L). (0242) The aqueous phase is discarded. The organic phase is clarified on a filter packed with active charcoal (921 g) and the cake is then washed with dichloromethane (10 L). The filtrate is then placed in the reactor and concentrated at reflux, distillate (37 L). Cyclohexane (43 L) is added to the reactor, which is then refluxed until the head temperature reaches 75 C. (distilled volume 22.5 L). Cyclohexane (10 L) is added and the reactor is allowed to cool to 27 C. An (S)-N-(2-bromo-6-methoxypyrid-4-yl)-2-hydroxy-2,4-dimethylpentanamide initiator (138 g; 0.42 mol; 0.02 eq.) is added to promote the crystallization. The reaction mixture is cooled to 20 C. and then filtered through a 25 mum filter gauze. (0243) The reactor and the filter are rinsed with cyclohexane (10 L). The solid is dried in an oven at 45 C. under vacuum to give (S)-N-(2-bromo-6-methoxypyrid-4-yl)-2-hydroxy-2,4-dimethylpentanamide (3.7 kg; 65%). (0244) 1H NMR (400 MHz, DMSO-d6): 10.0 (bs, 1H); 7.73 (s, 1H); 7.33 (s, 1H); 5.70 (bs, 1H); 3.80 (s, 3H); 1.79-1.67 (m, 2H); 1.49 (dd, J=13.6 & 5.2 Hz, 1H); 1.32 (s, 3H); 0.89 (d, J=6.4 Hz, 3H); 0.78 (d, J=6.4 Hz, 3H)

According to the analysis of related databases, 1196152-34-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Galderma Research & Development; BOITEAU, Jean-Guy; DAVER, Sebastien; RODEVILLE, Nicolas; (19 pag.)US2019/10124; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 96630-88-5, 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. 96630-88-5, name is 4-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, 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.

Example 66 Preparation of (4bR,8aR,9R)-N-(3-(2-(2-methoxyethoxy)ethoxy)pyridin-4-yl)-ll- methyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthren-3-amine (66), hydrochloride salt Step 1. Synthesis of 4-chloro-3-(2-(2-methoxyethoxy)ethoxy)pyridine, A mixture of 4-chloropyridin-3-ol (100 mg, 0.772 mmol), l-bromo-2-(2- methoxyethoxy)ethane (141 mg, 0.772 mmol) and CS2CO3 (503 mg, 1.544 mmol) in dimethylacetamide (5 mL) was irradiated in a microwave at 120 C for two hours. The reaction mixture was cooled to room temperature and poured into 20 mL of water. The aqueous solution was extracted with ethyl acetate 3×20 mL. The organic layer was combined, was washed with brine (50 mL), was dried over anhydrous sodium sulfate, was filtered and was concentrated. The crude product was purified via flash column chromatography on silica gel to afford 4-chloro-3-(2-(2-methoxyethoxy)ethoxy pyridine (87.4 mg, 48.9%). MS (EI) for C10H14CINO3: 232.0 (MH+).

According to the analysis of related databases, 96630-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEKTAR THERAPEUTICS; ANAND, Neel; AURRECOECHEA, Natalia; CHENG, Lin; DENG, Bo-liang; O’MAHONY, Donogh; MU, Yongqi; KROGH-JESPERSEN, Erik; (215 pag.)WO2016/182840; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 23628-31-1 ,Some common heterocyclic compound, 23628-31-1, molecular formula is C6H6N2O2, 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 1) Preparation of ethyl 6-aminopicolinate: To a solution of 2-amino-6-pyridinecarboxylic acid (6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 0 C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate (5.5 g, 76%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23628-31-1, its application will become more common.

Reference:
Patent; GlaxoSmithKline LLC; VU, Chi, B.; DISCH, Jeremy, S.; SPRINGER, Stephanie, K.; BLUM, Charles, A.; PERNI, Robert, B.; (212 pag.)EP2273992; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem