Day: April 8, 2022

Reference of 1111637-94-5 ,Some common heterocyclic compound, 1111637-94-5, molecular formula is C8H7BrN2, 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.

A solution of 19 (205.4 mg, 0.909 mmol) and 40 (150 mg, 0.909 mmol) in toluene/ ethanol (4 mL: 1 mL) was added sodium carbonate (190.8 mg, 1.818 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd(dppf)Cl2 (37.1 mg, 0.0454 mmol) was added to the reaction, which was degassed and purged with nitrogen for another 10 min, heated to 90 C. under sealed condition overnight, then allowed to cool to rt, and diluted with chloroform. The organic layer was filtered through Celite plug and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted in 50% ethyl acetate in hexane as off-white solid 88.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1111637-94-5, its application will become more common.

Reference:
Patent; ARRIEN PHARMACEUTICALS LLC; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; Gangireddy, Paramareddy; Appalaneni, Rajendra P.; US2014/315909; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1074-98-2 ,Some common heterocyclic compound, 1074-98-2, molecular formula is C6H6N2O3, 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.

3-Methyl-4-nitro-pyridine-N-oxide (5.34 g, 34.7 mmol, 1 equiv.) and N,N-dimethylformamide diethyl acetal (10.5 mL, 61.4 mmol, 1.8 equiv.) were combined in 50 mL anhydrous DMF and heated to 120 C. for 3 h. The reaction was allowed to cool back to room temperature and the DMF solvent was removed in vacuo. The residue was treated with ~80 mL toluene, which was then removed in vacuo as well. Finally the residue was mixed with benzene and filtered. The desired vinyl amine was obtained as a dark purple solid (6.74 g, 32.2 mmol, 93%), which was used as is in the next step. The vinyl amine from above (3.37 g, 16.1 mmol, 1 equiv.) and 1.75 mL of water were mixed in 50 mL EtOH. Ammonium formate (4.56 g, 72.5 mmol) and 10% palladium-on-carbon (600 mg) were added and the mixture was heated to a gentle reflux for 1 h. TLC and MS (ES+) revealed no starting material but showed the presence of two major components, the desired 5-aza-indole and its N-oxide. The reaction was left stirring for a further 2 h after more ammonium formate and more palladium catalyst were added. Finally the reaction was cooled to room temperature, filtered and solvents removed in vacuo. 5% NaOH aqueous solution was added and the mixture was extracted with EtOAc. The combined organics were dried (MgSO4), filtered, and the solvent was removed in vacuo, providing 0.555 g of desired 5-aza-indole (4.70 mmol, 29% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1074-98-2, its application will become more common.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US2003/162968; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 197376-47-9, 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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. A new synthetic method of this compound is introduced below.

2-(6-chloro-3-pyridyl)methyl-1,4,5,6-tetrahydropyrimidine [Compound 8] To a stirred solution of 20 ml of toluene were added 3.75 ml of 1M trimethylaluminum/hexane solution and 315 mul (3.77 mmol) of trimethylenediamine under argon atmosphere at room temperature, and to this mixture was further added 500 mg (2.5 mmol) of ethyl (6-chloro-3-pyridyl)acetate in toluene solution. The mixture was stirred for 22 hours at 100 C. under refluxing. After cooling the reaction mixture to room temperature, 5 ml of chloroform, 5 ml of methanol and 1 ml of water were added. Then precipitated gel was removed off by filtration and washed with a mixture of chloroform and methanol (9:1), and the filtrate was concentrated under reduced pressure. The resulting residue was purified by aminopropyl-coated silica gel (Chromatorex NH-type; Fuji Silysia Chemical Ltd.) column chromatography (eluent; dichloromethane:ethyl acetate=30:1, then dichloromethane_methanol=50:1) to give 442 mg (yield; 84.4%) of 2-(6-chloro-3-pyridyl)methyl-1,4,5,6-tetrahydropyrimidine as crystalline. This product was dissolved in methanol and to this solution was added 245 mg (2.11 mmol) of fumaric acid, and the mixture was concentrated under reduced pressure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,197376-47-9, its application will become more common.

Reference:
Patent; Imoto, Masahiro; Iwanami, Tatsuya; Akabane, Minako; Tani, Yoshihiro; US2003/100769; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 20511-15-3 ,Some common heterocyclic compound, 20511-15-3, molecular formula is C5H5ClN2, 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.

A 48% aqueous tetrafluoroboric acid solution (10 ml) was added to a solution of 4-chloropyridin-3-amine (1.29 g, 10.0 mmol) in ethanol (10 ml) at 0C. A solution of sodium nitrite (725 mg, 10.5 mmol) in water (10 ml) was added to the resultant mixed solution at the same temperature, and it was stirred at the same temperature for 30 minutes. The precipitate was collected by filtration and washed with ethanol, and the resultant brown solid (1.94 g) was then dissolved in acetonitrile (10 ml). A mixed solution of sodium cyanide (980 mg, 20.0 mmol) and copper(I) cyanide (896 mg, 10.0 mmol) in water (10 ml) and acetonitrile (1 ml) was added to the resultant solution at 0C, and it was stirred while gradually warming to room temperature for 10 hours. The reaction mixture was cooled to 0C, after which a saturated aqueous solution of sodium bicarbonate was added, and it was stirred for five minutes. The resultant solution was extracted with ethyl acetate, and the organic layer was then washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, followed by concentration under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to yield the title compound (605 mg, 44%) as a pale yellow solid. 1H-NMR (300 MHz, CDCl3) delta: 8.87 (1H, s), 8.72 (1H, d, J = 3.9 Hz), 7.51 (1H, d, J = 3.9 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,20511-15-3, its application will become more common.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; MURATA, Takeshi; KAWADA, Hatsuo; NIIZUMA, Satoshi; HARA, Sousuke; HADA, Kihito; SHIMADA, Hideaki; TANAKA, Hiroshi; MIO, Toshiyuki; EP2842946; (2015); 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. 936011-17-5, name is 5-Bromo-2-methoxyisonicotinaldehyde. A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-2-methoxyisonicotinaldehyde

General procedure: In a round-bottom flask, to aldehyde (1.0 mmol) in DMF(1 mL) was added sulfinamide (2 or 2a) (1.5 mmol) followed by DBU (1.5 mmol). The solution was allowed to stirat room temperature for 2-10 h. The progress of the reaction was monitored by TLC. After complete conversion, the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated. The crude product was subjected to column chromatography on silica gel (eluent:petroleum ether/ethyl acetate = 80:20) to provide the corresponding N-sulfinyl imines.

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, 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde.

Reference:
Article; Ramaiah, Manjunatha M; Shubha, Priya Babu; Prabhala, Pavan Kumar; Shivananju, Nanjunda Swamy; Journal of Chemical Research; vol. 44; 1-2; (2020); p. 72 – 79;,
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. 851607-27-7, name is 5-Bromo-4-chloro-2-methoxypyridine. A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-4-chloro-2-methoxypyridine

An eighth exemplary Intermediate D, Intermediate D-8, may be used to synthesize compounds of formula I, wherein R1 is heteroaryl substituted with two R4 substituents. To a solution of //-butyllithium (2.50 M, 1.80 mL, 1.00 equiv) was added dropwise over one min to i- PrMgCl (2.00 M, 1.12 mL, 0.500 equiv) in THF (12 mL) at 0 C under a nitrogen atmosphere. The mixture was stirred at 0 C for 5 min followed by the addition of 5-bromo-4-chloro-2- methoxy-pyridine (1.00 g, 4.50 mmol, 1.00 equiv) after which the mixture was stirred at 0 C for 45 min. To this solution was added 2-isopropoxy-4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolane (836 mg, 4.50 mmol, 917 uL, 1.00 equiv) and the mixture stirred for an additional 15 min prior to stirring at 20 C for 3 h. The reaction mixture was quenched by the addition of satd aq ammonium chloride (20.0 mL) at 20 C and was extracted with ethyl acetate (20.0 mL x 3). The combined organic layers were washed with brine (10.0 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 4-chloro-2-methoxy-5-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)pyridine (1.00 g, 3.71 mmol, 82.5% yield) as a gray solid, which used for the next step without further purification. 1H NMR (400 MHz, CDCl3) d = 8.47 (s, 1H), 6.77 (s, 1H), 3.97 (s, 3H), 1.38 (s, 12H).

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, 851607-27-7, 5-Bromo-4-chloro-2-methoxypyridine.

Reference:
Patent; MIRATI THERAPEUTICS, INC; MARX, Matthew, Arnold; LEE, Matthew, Randolph; BOBINSKI, Thomas, P.; BURNS, Aaron, Craig; ARORA, Nidhi; CHRISTENSEN, James, Gail; KETCHAM, John, Nichael; (225 pag.)WO2019/152419; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 120422-90-4, name is 4,6-Dichloro-3-methyl-1H-pyrazolo[4,3-c]pyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

A mixture of Intermediate 4 (33 mg, 0.163 mmol) and cyclohexylamine (19 muIota, 0.163 mmol) in n-butanol (1 ml) was stirred at rt overnight, monitoring the reaction by LC/MS. The mixture was heated to 100C overnight and more cyclohexylamine (57 muIota, 0.499 mmol) was added and stirring was continued at 100C overnight. The mixture was then diluted with ethyl acetate and washed with water and brine. The organic phase was dried and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 2:1 petrol-ethyl acetate to give an off-white coloured solid (10 mg, 23%). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.13 – 1.25 (m, 1 H), 1.28 – 1.47 (m, 4 H), 1.58 – 1.66 (m, 1 H), 1.69 – 1.79 (m, 2 H), 1.90 – 1.97 (m, 2 H), 2.56 (s, 3 H), 3.91 – 4.01 (m, 1 H), 5.85 (d, J=7.8 Hz, 1 H), 6.56 (s, 1 H). m/z (ES+APCI)+ : 265/267 [M+H]+

The synthetic route of 120422-90-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; CHAN, Brayn; ESTRADA, Anthony; SWEENEY, Zachary; MCIVER, Edward Giles; WO2011/141756; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59290-81-2, Adding some certain compound to certain chemical reactions, such as: 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid,molecular formula is C7H6N2O4, 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 59290-81-2.

Compound D5 (208g, 1.15mol) was dissolved in t-butanol (2.1L), and thereto were added DPPA (37OmL) and TEA (223mL). The mixture was heated under reflux overnight, quenched by the addition of brine (10OmL). The resulting mixture was extracted by EA (1.0L) for three times. The combined organic phase was washed with brine (10OmL), dried over anhydrous MgSO4 and concentrated under vacuo. The residue was purified by column chromatography (EA : PE=I :2) to provide compound D6 (1 14.5g, 40% yield) as yellow solid. IH NMR (CDC13, 300MHz): delta=l .54 (s, 9H), 2.60 (s, 3H), 6.53 (s, IH), 8.98-8.99 (d, IH), 9.09-9.10 (d, IH). LC-MS [M+l] +: 252.0.

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. 59290-81-2, 2-Methyl-5-nitro-3-pyridinecarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; XCOVERY, INC.; WO2008/88881; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13958-93-5 ,Some common heterocyclic compound, 13958-93-5, molecular formula is C6H3Cl2NO2, 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.

Example 8 difluorocyclobutanecarboxamide.2HCI; 3,5-Dichloroiso?icotinic acid (84mg, 0.4mmol), the compound of Preparation 42 (150mg, 0.3mmol), 3- (diethoxyphosphoryloxy)-1 ,2,3-benzotriazin-4(3H)-one (132mg, 0.4mmol) and triethylamine (0.16mL, 1.2mmol) were dissolved in dichloromethane and stirred at room temperature for 24hours. The reaction was quenched by the addition of saturated sodium hydrogen carbonate solution and extracted using dichloromethane. The combined organic extracts were concentrated in vacuo to give the crude product. The crude mixture was purified by column chromatography on silica gel using dichloromethane-.methanol EPO (100:0 to 90:10) as eluent. The resulting product was then dissolved in dichloromethane (5mL) and treated with 2M hydrochloric acid in diethyl ether (5mL), the solvents were removed in vacuo to give 43mg of title compound as a white solid.1H NMR (400MHz CDCI3) delta 0.95 (3H, s), 1.20-1.85 (9H, m), 1.85-2.00 (1 H, m), 2.05-2.30 (2H, m), 2.45(1 H, bs), 2.70-3.10 (6H, m), 3.25-3.50 (2H, m), 4.05-4.20 (1H, m), 4.40-4.65 (2H, m), 7.10-7.40 (5H1 m),8.50 (2H, bs).LRMS: m/z APCI+579[MH+]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13958-93-5, its application will become more common.

Reference:
Patent; PFIZER LIMITED; WO2006/77499; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59942-87-9 ,Some common heterocyclic compound, 59942-87-9, molecular formula is C7H6N2O, 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.

Example 13: Synthesis of 4-(2-(pyrazolo[1 ,5-a]pyridin-2-yloxy)ethyl)morpholine To a solution of pyrazolo[1 ,5-a]pyridin-2-ol (120 mg, 0.89 mmol) in 4 ml_ of anhydrous DMF, were added K2C03 (270 mg, 1 .95 mmol), 4-(2-chloroethyl)morpholine hydrochloride (183 mg, 0.98 mmol) and Nal (134 mg, 0.89 mmol) and the mixture heated to 80 5C for 18 h under nitrogen. The solvent was evaporated under reduced pressure and the residue poured into a mixture of EtOAc and water, to afford after drying and evaporation of organic layers, 1 12 mg of an oil that was purified by silica gel flash chromatography with EtOAc/MeOH (9:1 ) as eluent to afford 57 mg of 4-(2- (pyrazolo[1 ,5-a]pyridin-2-yloxy)ethyl)morpholine. 40 mg (0.43 mmol) of anhydrous oxalic acid in 0.5 ml_ of acetone were added to a solution of 98 mg of 4-(2- (pyrazolo[1 ,5-a]pyridin-2-yloxy)ethyl)morpholine base oil in 0.5 ml_ of acetone. The solid is filtered and washed with diethyl ether to give 133 mg (90%). 1 H NMR (DMSO) delta ppm: 8.46 (d, J = 6.9 Hz, 1 H), 7.46 (d, J = 8.9 Hz, 1 H), 7.26 – 7.09 (m, 1 H), 6.74 (td, J = 6.9, 1 .4 Hz, 1 H), 6.00 (s, 1 H), 4.41 (t, J = 5.3 Hz, 2H), 3.74 – 3.60 (m, 4H), 3.07 (t, J = 5.2 Hz, 2H), 2.92 – 2.66 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59942-87-9, its application will become more common.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE S.A.; DIAZ FERNANDEZ, Jose Luis; CUBERES ALTISENT, Mª Rosa; WO2013/124341; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem