Day: March 24, 2022

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

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

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

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

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

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. 502509-10-6, name is 4-(2-Hydroxyethyl)picolinic acid. A new synthetic method of this compound is introduced below., Formula: C8H9NO3

To a stirred solution of acid 70 (4.76 g, 23.4 mmol) acid in MeOH (104 mL) at 0 C was slowly added thionyl chloride (3.40 mL, 46.8 mmol) and was heated at reflux during 24 h. After cooling at 0 C, thionyl chloride (3.40 mL, 46.8 mmol) was added in second time and heated at reflux during 24 h. Then, the mixture was concentrated in vacuo and a saturated aqueous solution of NaHCO3 was added until basic pH. The aqueous layer was extracted with EtOAc (thrice). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford 36 as black oil in 38% yield (1.60 g). The crude product was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) delta 8.43 (d, J = 4.9 Hz, 1H), 7.90 (d, J = 0.9 Hz, 1H), 7.27 (dd, J = 5.0, 1.7 Hz, 1H), 3.88 (s, 3H), 3.84 (t, J = 6.4 Hz, 2H), 3.44 (bs, 1H), 2.83 (t, J = 6.3 Hz, 2H). 13C NMR (75 MHz, CDCl3) delta 165.6, 150.2, 149.3, 147.3, 127.8, 125.8, 61.7, 52.7, 38.2. MS (ESI+): m/z (%): 182 (100) [M+H]+.

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, 502509-10-6, 4-(2-Hydroxyethyl)picolinic acid.

Reference:
Article; Oukoloff, Killian; Coquelle, Nicolas; Bartolini, Manuela; Naldi, Marina; Le Guevel, Remy; Bach, Stephane; Josselin, Beatrice; Ruchaud, Sandrine; Catto, Marco; Pisani, Leonardo; Denora, Nunzio; Iacobazzi, Rosa Maria; Silman, Israel; Sussman, Joel L.; Buron, Frederic; Colletier, Jacques-Philippe; Jean, Ludovic; Routier, Sylvain; Renard, Pierre-Yves; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 58 – 77;,
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.92992-85-3, name is 2-Bromo-3,5-dimethylpyridine, molecular formula is C7H8BrN, molecular weight is 186.0491, as common compound, the synthetic route is as follows.HPLC of Formula: C7H8BrN

[0085 -Step e: Preparation of 2′,5′-dichloro-3,5-dimethyl-2,4′-bipyridine [0086] To a solution of 2,5-dichloropyridin-4-ylboromc acid (7.56 g, 40 mmol), 2-bromo- 3,5- dimethylpyridine (5.62 g, 30 mol) in dioxane (60 mL) and H?0 (12 mL) were added Pd(dppf)CI2 (1.35 g, 1.7 mmol) and K :'( ) · 31 >( > (16.2 g, 60 mmol), the mixture was stirred at reflux under N2 atmosphere overnight. TLC showed the reaction was complete. After cooling to room temperature, the mixture was filtered. Water (50 mL) was then added to the filtrate. The mixture was extracted with dichloromethane (150 mL x 3). The combined organic layers were washed with brine (300 mL), dried over Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc = 20:1 to 10:1) to give title compound (3.1 g, 41%) as a white solid. NMR (400MHz, CDCI3): delta 8.46 (s, 1 H), 8.37 (s, 1 H), 7.47 (s, 1 H), 7.33 (s, 1 H), 2.39 (s, 3H), 2.16 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,92992-85-3, 2-Bromo-3,5-dimethylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; ZHANG, Xiaohu; WO2014/113191; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 16727-47-2, Adding some certain compound to certain chemical reactions, such as: 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine,molecular formula is C19H16BrNO2, 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 16727-47-2.

To a stirred solution of 16-1 (5.0 g, 13.5 mmol) in Dioxane (20 mL) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (5.12 g, 20.2 mmol) and KOAc (2.64 g, 27.0 mmol). The reaction mixture was degassed with argon for 10 minutes. PdCl2(dppf).DCM (1.10 g, 1.35 mmol) was added and the resulting mixture was stirred at 100 oC for 16 hours. The reaction was then cooled to room temperature and filtered through a short bed of celite. The filtrate was diluted with Ethyl acetate, washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude mass was purified by column chromatography (silica, gradient: 0-5% Ethyl acetate in Hexane) to afford 25-1 (3.5 g, 62%) as a pale yellow solid.

According to the analysis of related databases, 16727-47-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17117-17-8, 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 17117-17-8 as follows.

(4E)-N-Methyl-N-(tert-butoxycarbonyl)-5-(5-ethoxy-3-pyridyl)-4-penten-2-amine Under a nitrogen atmosphere, a mixture of 5-ethoxy-3-bromopyridine (1.20 g, 5.94 mmol), N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine (1.18 g, 5.94 mmol), palladium(II) acetate (13.5 mg, 0.06 mmol), tri-o-tolylphosphine (73.1 mg, 0.24 mmol), triethylamine (1.5 mL, 10.8 mmol), and anhydrous acetonitrile (3 mL) was stirred and heated under reflux at 80-85 C. for 28 h. The resulting mixture, containing beige solids, was cooled to ambient temperature, diluted with water (20 mL), and extracted with CHCl3 (3*20 mL). The combined light-yellow CHCl3 extracts were dried (Na2SO4), filtered, concentrated by rotary evaporation, and vacuum dried producing a yellow oil (1.69 g). The crude product was purified by column chromatography on silica gel (100 g), eluding with ethyl acetate-hexane (1:1, v/v). Selected fractions containing the product (Rf 0.20) were combined, concentrated by rotary evaporation, and the residue was vacuum dried to give 0.67 g (35.2%) of a light-yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17117-17-8, its application will become more common.

Reference:
Patent; Caldwell, William S.; Dull, Gary M.; Bhatti, Balwinder S.; Hadimani, Srishailkumar B.; Park, Haeil; Wagner, Jared M.; Crooks, Peter A.; Lippiello, Patrick M.; Bencherif, Merouane; US2003/125345; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 54-92-2, Adding some certain compound to certain chemical reactions, such as: 54-92-2, name is N’-Isopropylisonicotinohydrazide,molecular formula is C9H13N3O, 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 54-92-2.

A solution of 3-(2′,3′-dimethyl-biphenyl-2-yl)-propionic acid (127 mg, 0.50 mmoles) and isonicotinic acid N’-isopropyl-hydrazyde (ACROS) (167 mg, 0.60 mmoles) in DMF (5 mL) was treated with diisopropylethylamine (0.35 mL, 2.0 mmoles), and PyBroP (350 mg, 0.75 mmoles) at room temperature for 16 h. The reaction mixture was partitioned between 1N NaOH and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with 100% ethyl acetate to afford the product (17 mg, 8%). LC-MS m/e 416.49 (M+H+)

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. 54-92-2, N’-Isopropylisonicotinohydrazide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Michoud, Christophe; US2006/258740; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem