Month: March 2021

Synthetic Route of 889676-37-3 ,Some common heterocyclic compound, 889676-37-3, molecular formula is C6H5BrN2O, 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.

5-methoxybenzofuran boronic acid (1.2 mmol), 6-bromonicotinamide (1.0 mmol), Pd(PPh3)2Cl2 (0.024 mmol) and NEt3 (317 muL) were mixed in EtOH (10 mL) in a 20 mL microwave vial. The mixture was stirred at 140 C. for 10 min in a microwave reactor. The mixture was filtered, the obtained precipitate was washed with water and EtOAc and dried under vacuum to afford the title compound (85 mg). 1H NMR delta ppm 9.14 (d, 1H) 8.42 (dd, 1H) 7.97-8.25 (m, 2H) 7.63-7.80 (m, 2H) 7.58 (d, 1H) 7.22 (d, 1H) 6.98 (dd, 1H) 3.81 (s, 3H); MS m/z 269 (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. 889676-37-3, 6-Bromonicotinamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; US2008/221149; (2008); 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 846021-26-9, name is 2-Amino-6-methylnicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H8N2O2

Production example 63 A mixture of 0.27 g of 4-(3-methoxyphenoxy)benzylamine, 0.15 g of 2-amino-6-methylnicotinic acid, 0.15 g of 1-hydroxybenzotriazole, 0.25 g of WSC, 0.35 g of pyridine and 2 ml ofDMF was stirred under heating to reflux for 30 minutes, and then at a room temperature for 1 day. Thereafter, water was added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was successively washed with a sodium bicarbonate aqueous solution, water, MTBE and hexane, and it was then dried, so as to obtain 0.25 g of N-[4-(3-methoxyphenoxy)phenyl]methyl-2-amino-6-methylnicotinic acid amide (hereinafter referred to as the present compound 79).The present compound 79 [Show Image] 1H-NMR (CDCl3) delta: 2.38 (3H, s), 3.78 (3H, s), 4.56 (2H, d, J = 5.6 Hz), 6.24 (1H, br s), 6.38 (2H, br s), 6.44 (1H, d, J = 7.7 Hz), 6.53-6.68 (3H, m), 7.00 (2H, d, J = 8.7 Hz), 7.20-7.25 (1H, m), 7.28-7.32 (2H, m), 7.49 (1H, d, J = 7.7 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 846021-26-9.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2248423; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 63897-12-1 ,Some common heterocyclic compound, 63897-12-1, molecular formula is C6H4Cl2N2O2, 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.

PREPARATION 10; Benzyl-(2-chloro-6-methyl-3-nitro-pyridin-4-yl)-amine; 2,4-Dichloro-6-methyl-3-nitro-pyridine (2 g, 9.7 mmol) and triethylamine (1.35 mL, 9.7 mmol) were dissolved in 40 mL THF and cooled (ice/water) to 5 C. A solution of benzylamine (1.04 g, 9.7 mmol) in 10 mL THF was added dropwise and the mixture was then allowed to warm gradually to room temperature overnight. The mixture was evaporated in vacuo, partitioned between EtOAc (50 mL) and water (20 mL). The organic layer was washed with saturated aqueous NaHCO3 (10 mL), dried (MgSO4) and evaporated in vacuo to an orange gum. This gum was preabsorbed onto silica gel and then purified by column chromatography, eluting with DCM:pentane 3:1. Appropriate fractions combined and evaporated in vacuo to yield the title compound as a yellow solid (716 mg).1H NMR (CDCl3) 2.32 (s, 3H), 4.38 (d, 2H), 6.39 (s, 1H), 6.90 (broad s, 1H), 7.21 (m, 2H), 7.29 (m, 3H). LC-MS (ELSD, ES+) m/z 278 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63897-12-1, its application will become more common.

Reference:
Patent; PFIZER LIMITED; US2007/197478; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 62150-45-2, 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.62150-45-2, name is 4-Bromopyridine-2-carbonitrile, molecular formula is C6H3BrN2, molecular weight is 183.01, as common compound, the synthetic route is as follows.

[00842] 4-bromopyridine-2-carbonitrile (150 mg, 0.82 mmol), phenyl formate (0.12 ml, 1.07 mmol), palladium(II) acetate (5.52 mg, 0.02 mmol), tri-tert-butylphosphonium tetrafluoroborate (28.54 mg, 0.1 mmol) and N,N-diethylethanamine (0.15 ml, 1.07 mmol) were added to a microwave vessel under an atmosphere of nitrogen. The reaction vessel was de-gassed and back filled with nitrogen (x3), sealed and heated at 140 ¡ãC for 20 mins under microwave irradiation. A further portion of palladium(II) acetate (5.52 mg, 0.02 mmol) and tri-tert-butylphosphonium tetrafluoroborate (28.54 mg, 0.1 mmol) was added and the reaction vessel de-gassed and back filled with nitrogen (x3), sealed and heated at 140 ¡ãC for 45 mins under microwave irradiation. The resultant mixture was diluted with water (4 mL) and DCM (3 mL), stirred vigorously and the phases separated using a phase separator cartridge. The aqueous was re-extracted with DCM (x2) and the organic extracts separated using a phase separator. The combined organic extracts were concentrated in vacuo and purified by chromatography on Si02, eluting with Heptane/EtOAc (gradient 100:0 – 55:45) to afford the title compound (94 mg, 51percent) as a pale yellow gum that solidified on standing. [00843] Method B: LC-MS m/z = 224.9 [M + H]+; RT = 1.11 min.

Statistics shows that 62150-45-2 is playing an increasingly important role. we look forward to future research findings about 4-Bromopyridine-2-carbonitrile.

Reference:
Patent; QUARTET MEDICINE, INC.; ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL); TEBBE, Mark, Joseph; ATTON, Holly, Victoria; AVERY, Craig; BROMIDGE, Steven, Mark; KERRY, Mark; KOTEY, Adrian, Kotei; MONCK, Nathaniel, J.; MENICONI, Mirco; RIDGILL, Mark, Peter; TYE, Heather; SAIAH, Eddine; JOHNSSON, Kai, Peter; GORSKA, Katarzyna, Irena; PENG, Hairuo; MCCALL, John, Michael; (356 pag.)WO2017/59191; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1849-53-2, Adding some certain compound to certain chemical reactions, such as: 1849-53-2, name is 3-Methoxypicolinaldehyde,molecular formula is C7H7NO2, 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 1849-53-2.

The compound (31.6 mg) obtained in Example 1-5 was dissolved in methanol (0.3 ml), and the solution was added with 3-methoxy-2-pyridinealdehyde (11.3 mg) that had been synthesized in accordance with a method described in Cominus D. et al ., Tetrahedron Lett., 29 (7), 773 (1988) and stirred at room temperature for 4.5 hours. After completion of reaction, the solvent was distilled off, and the residue was dried in vacuum and re-dissolved in methanol (0.6 ml). The solution was ice-cooled, and sodium borohydride (9 mg) was added to the solution. The resultant solution was returned to room temperature and stirred for 30 minutes. After completion of reaction, the solvent was distilled off, and the residue was dissolved in chloroform. The resultant solution was washed with 0.5 mol/l sodium hydroxide and brine and dried with anhydrous sodium sulfate, and the solvent was distilled off. The residuewas dissolved in chloroform (0.9ml), and methanesulfonic acid (40mul) and methanol (40 mul) were added under ice-cooling, followed by stirring at room temperature for 1.5 hours. After completion of reaction, the solvent was distilled off, and the residue was purified by silica gel column chromatography (chloroform/methanol/water = 7/3/0.5), to thereby obtain a methanesulfonate (36.1 mg) of the subject compound as a white solid. MS(FAB,Pos.):m/z=620[M+1]+1H-NMR(500MHz,DMSO-d6):delta=1.52(3H,d,J=7.1Hz),1.65-1.82(6H,m),2.3 6(12H,s),2.97-3.05(2H,m),3.86(3H,s),4.22(2H,t,J=5.9Hz),4.34(2H ,s),4.46(2H,br),4.55-4.62(1H,m),5.71(1H,quint.,J=7.1Hz),7.43-7 .60(6H,m),7.61(2H,d,J=8.1Hz),7.70(2H,brs),7.83(1H,d,J=7.8Hz),7 .94(1H,d,J=7.1Hz),7.98(2H,d,J=8.1Hz),8.10(1H,d,J=8.5Hz),8.18(1 H,d,J=4.6Hz),8.55(1H,br),8.72(1H,d,J=7.8Hz),8.94(2H,brs).

According to the analysis of related databases, 1849-53-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1431290; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 893423-62-6 , The common heterocyclic compound, 893423-62-6, name is tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamate, molecular formula is C11H13ClN2O3, 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 solution of tert-butyl (2-chloro-3-formyl-4-pyridinyl)carbamate (1-5) (10 g,39 mmol) and DBU (12 niL, 78 mmol) in THF (130 mL) was added phenylacethyl chloride (5.7 mL, 43 mmol) at 00C. The reaction was allowed to slowly warm to room temperature for overnight. The solvent was removed under reduced pressure, and the residue was diluted with EtOAc, washed with IN HCl, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give tert-butyl 5-chloro-2- oxo-3-phenyl-l,6-naphthyridine-l(2H)-carbamate (62-1) as a colorless solid.

The synthetic route of 893423-62-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BANYU PHARMACEUTICAL CO., LTD.; ARMSTRONG, Donna, J.; GOTO, Yasuhiro; HASHIHAYATA, Takashi; KATO, Tetsuya; KELLY, Michael, J., III; LAYTON, Mark, E.; LINDSLEY, Craig, W.; OGINO, Yoshio; ONOZAKI, Yu; RODZINAK, Kevin, J.; ROSSI, Michael, A.; SANDERSON, Philip, E.; WANG, Jiabing; YAROSCHAK, Melissa, M.; WO2010/88177; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 571189-16-7, 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. 571189-16-7, name is tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate. A new synthetic method of this compound is introduced below.

Add 100 ml of methanol, 0.10 g of 10% palladium carbon to 100 ml of the reaction vessel, and add 1.8 g of 4-(6-nitropyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester. The system is closed and nitrogen-filled to 0.3. MPa, replacement twice, pass H2 to the reactor pressure 0.3MPa, replace once, then start the reaction at room temperature, reaction 12h, HPLC analysis of the reaction solution, the raw material content is less than 0.5%. The reaction solution was filtered under reduced pressure through a 0.45 um organic filter, and then evaporated to dryness to give a white solid 1.71 g, product yield 95%, purity over 99%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,571189-16-7, tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Suzhou Laikeshide Pharmaceutical Co., Ltd.; Wang Aifeng; Liu Chuantao; Zhang Caihui; Yu Jurong; (7 pag.)CN108558745; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14432-12-3, 4-Amino-2-chloropyridine, 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, 14432-12-3, blongs to pyridine-derivatives compound. category: pyridine-derivatives

(a) Sodium azide (1.31 g) and ammonium chloride (1.07 g) were added to a solution of 4-amino-2-chloropyridine (2 g) in dimethylformamide (20 ml) and the mixture was stirred at 110 C. for 10 hours. After the insoluble material was filtered off, the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to give 1.83 g of 4-amino-2-azidopyridine, melting point 220 C. (decomposition). PMR(DMSO-d6 /TMS) delta: 6.55(2H, s), 6.67(1H,d,J=2 Hz), 6.76(1H, dd, J=2,8 Hz), 8.78(1H,d,J=8 Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14432-12-3, its application will become more common.

Reference:
Patent; Yoshitomi Pharmaceutical Industries, Ltd.; US5478838; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 215364-85-5, 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. 215364-85-5, name is 3-Bromo-2-chloropyridin-4-amine, molecular formula is C5H4BrClN2, 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 2 L 3 neck RBF was charged with 3-bromo-2-chloro-4-amino-pyridine (50.0 g, 241 mmol) in concentrated H2SO4 (36 mL) at 0 C. open to air. KNO3 (48.7 g, 482 mmol) was then added. The solution was allowed to first warm to room temperature (rt) for 1 h and then was heated to 90 C. for 3 h. The reaction mixture was cooled to rt and was poured into ice water. The obtained solids were filtered and washed with water. After drying under vacuum overnight 3-bromo-2-chloro-5-nitropyridin-4-amine was obtained as an orange-yellow solid (49 g, 81%). This was used directly without further purification.

According to the analysis of related databases, 215364-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Universal Display Corporation; Layek, Suman; Ji, Zhiqiang; Dyatkin, Alexey Borisovich; Boudreault, Pierre-Luc T.; Tsai, Jui-Yi; (251 pag.)US2019/393431; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 886365-56-6, 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 886365-56-6 as follows.

A mixture of 5-fluoro-3-methylpyridin-2-amine (3.3 g, 26.2 mmol) and dimethyl malonate(15.0 mL, 0.13 mol, 5.0 eq.) was heated at 210 C for 1.5 h. After cooling to room temperature,the precipitate was filtered and washed with ACN (3x) to give 7-fluoro-2-hydroxy-9-methyl- pyrido[1,2-a]pyrimidin-4-one as a dark solid (2.3 g), which was used directly in the next step. MS mlz 195.1 [M+H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,886365-56-6, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GILLESPIE, Robert Jack; HASANE, Ratni; SARIE, Jerome Charles; (89 pag.)WO2016/184832; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem