Day: April 8, 2022

Adding a certain compound to certain chemical reactions, such as: 13958-85-5, 3-Fluoro-5-methylpyridin-4-amine, 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, COA of Formula: C6H7FN2, blongs to pyridine-derivatives compound. COA of Formula: C6H7FN2

General procedure: Pd2dba3 (8.25 mg, 9.01 pmol), XantPhos (13.0 mg, 22.5 pmol) and Cs2C03 (110 mg, 0.34 mmol) were dissolved in DMF (2.25 mL) in a sealed tube while N2 was bubbling. 1-49 (42.0 mg, 0.25 mmol) and 1-1 (53.5 mg. 0.23 mmol) were added and the reaction mixture was stirred at room temperature for 10 min. Then, the reaction mixture was heated at 110 C for 20 h. The reaction mixture was cooled to room temperature, filtered through Celite and washed with EtOAc. The solvent was removed under reduced pressure and the crude mixture was purified by reverse phase column chromatography (mobile phase: HCOOH (0.l%)/(MeCN:MeOH, 1 :1), gradient from 95:5 to 63:37) to afford compound 91 (42 mg, 50%) as a white solid.

The synthetic route of 13958-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; LEENAERTS, Joseph, Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; MARTINEZ LAMENCA, Carolina; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (110 pag.)WO2019/243533; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17570-98-8, 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. 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, 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.

B) Synthesis of 2- (pyridin-2-yl)-2-bromomethyl-4-hydrox methyl-1, 3-dioxolane cisltrans 316 ml of glycerol were dissolved in 2 1 of toluene and 13.6 g of p- toluenesulfonic acid and 195 g of 2-bromoacetyl-pyridine hydrobromide were added to this solution. The reaction mixture was refluxed for 24 hours, with removal of the water present in the azeotrope. Once the mixture had cooled to ambient temperature, 2 1 of 5% NaHCO3 were added, the two-phase mixture was stirred for 5 minutes and the phases were then separated. The aqueous phase was extracted six times with 600 ml of toluene, the organic phases were combined, dehydrated with Na2S04, and evaporated to dryness under reduced pressure, giving rise to 80 g of (cis/trans)-2-(pyridin-2-yl)-2-bromomethyl-4- hydroxymethyl-1,3-dioxolane (yield 42%).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide.

Reference:
Patent; ITALFARMACO S.P.A.; WO2005/40156; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 51173-05-8, 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. 51173-05-8, name is 5-Fluoro-2-hydroxypyridine, molecular formula is C5H4FNO, 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.

Compound 4-80 was dissolved in sulfuric acid (the larger amounts indicated above) at rt and then heated to 65 C. A preformed solution of fuming nitric acid and sulfuric acid (the smaller amount indicated above) was added dropwise. The temperature was kept between 65 C. and 80 C. (rxn is exothermic and although the bath is at 65 C., temperature goes higher, usually 75, sometimes 80 C.). After the addition was complete, the reaction mixture was heated at 65 C. for an additional hr. The reaction mixture was then cooled to rt and poured in a flask containing ice) (20 g of ice/gr compound, evolution of gas occurred). A solid precipitated out and it was collected by filtration (1HNM showed 4-80 and something else (discarded)). The aqueous layer was extracted with AcOEt several times (3-5) and concentrated on a rotary evaporator under vacuum to afford a solid that was triturated with ether to afford 5-80 as a bright yellow solid. A total of 117 g of desired product was collected in the first crop (27% yield from diazonium salt). A portion did not crystallize: this oil was triturated with MeOH and Et2O to afford 3.6 g of 5-80; another precipitation from the mother liquid afforded an additional 6.23 g of the desired product 5-80. Total: 117.0+3.6+6.23=126.83. 30.4%). Yield for 3 steps (decomposition of diazonium salt; deprotection and nitration). Analytical data from Notebook: 53877-115: 1HNMR(delta, MeOD): 8.56-8.27 (dd, J=7.5, 3.3 Hz, 1H), 8.01 (d, J=3.3 Hz, 1H); LC/MS(M+1)+=158.9; rt=0.15 min. Note: A portion of the aqueous acidic solution was taken and neutralized with Na2CO3 until effervescence stopped and then it was extracted with AcOEt A different product was obtained. No desired product in these extracts.

According to the analysis of related databases, 51173-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ueda, Yasutsugu; Connolly, Timothy P.; Kadow, John F.; Meanwell, Nicholas A.; Wang, Tao; Chen, Chung-Pin H.; Yeung, Kap-Sun; Zhang, Zhongxing; Leahy, David Kenneth; Pack, Shawn K.; Soundararajan, Nachimuthu; Sirard, Pierre; Levesque, Kathia; Thoraval, Dominique; US2005/209246; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211532-15-8, 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. 1211532-15-8, name is 6-Methoxy-5-(trifluoromethyl)nicotinic acid, molecular formula is C8H6F3NO3, 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.

N,O-dimethylhydroxylamine hydrochloride (4.3 g), N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride(9.5 g), and N,N-diisopropylethylamine (30 mL) were added to a mixture of 6-methoxy-5-(trifluoromethyl)nicotinicacid (7.8 g) and methylene chloride (80 mL) under ice-cooling, and then the reaction mixture was stirred at room temperaturefor 17 hours. The reaction mixture was concentrated under reduced pressure, and to the residue were addedethyl acetate and water, followed by stirring for 30 minutes. The mixture was extracted with ethyl acetate, the organiclayer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residuewas purified by silica gel column chromatography (hexane-ethyl acetate) to N,6-dimethoxy-N-methyl-5-(trifluoromethyl)nicotinamide (5.0 g) as an oil.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1211532-15-8, 6-Methoxy-5-(trifluoromethyl)nicotinic acid.

Reference:
Patent; Astellas Pharma Inc.; TAKAHASHI, Taisuke; TANAKA, Hiroaki; AKAIWA, Michinori; NEGORO, Kenji; MIHARA, Hisashi; FUJI, Hideyoshi; TAKAMATSU, Hajime; (133 pag.)EP3196200; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 886365-46-4, 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 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Crude tert-butyl ((4aRS,11bRS)-10-amino-3,3,11b-trimethyl-4,4-dioxido-4-a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (70 mg, 0.165 mmol) was suspended in DMF (2 ml) and sonicated for 1 min. 5-Chloro-3-methylpyridine-2-carboxylic acid (34.0 mg, 0.198 mmol), pyridine (0.04 ml, 0.496 mmol) and HATU (94 mg, 0.248 mmol) were added and resulting suspension was stirred for 45 min at RT. The mixture was diluted with EtOAc (8 ml) and saturated NaHCO3 solution (3 ml). Water was added to dissolve precipitated solids. The organic layer was separated, washed with water and concentrated, and the resulting concentrate/residue was purified by FC on 12 g RediSep Gold column using 10-80% EtOAc in heptane to afford tert-butyl ((4aRS,11bRS)-10-(5-chloro-3-methylpicolinamido)-3,3,11b-trimethyl-4,4-dioxido-4-a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (76 mg, 0.132 mmol, 80% yield) as white solid.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid.

Reference:
Patent; WHITE, Ryan; ALLEN, Jennifer R.; EPSTEIN, Oleg; HONG, Fang-Tsao; HUA, Zihao; HUMAN, Jason Brooks; LOPEZ, Patricia; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; TAMAYO, Nuria A.; ZHENG, Xiao Mei; US2014/213581; (2014); 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 6515-09-9, name is 2,3,6-Trichloropyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H2Cl3N

A mixture of 2,3,6-trichloropyridine (18.2 g, 0.1 mol)Pd / C (10%) (2.73 g),1-isopropyl-4-methylcyclohexene (69 g, 0.5 mol) was added to methanol (182 g)Slowly heated to 60 C for 4 hours;After the reaction,The methanol was distilled off by distillation and vacuum distillation,Add water (100 g),The mixture of 2,3-dichloropyridine and water was distilled off by steam distillation at atmospheric pressure,Cooled by filtration to obtain 2,3-dichloropyridine 14g,Purity (HPLC) ?98%Yield 95%.

With the rapid development of chemical substances, we look forward to future research findings about 6515-09-9.

Reference:
Patent; Jiangsu Zhongbang Pharmaceutical Co., Ltd.; Qian, Yong; Xu, Qiang; Gao, Qian; Zhao, Huayang; Zhang, Xiaoqing; (5 pag.)CN106518754; (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 1227002-03-0, name is Methyl 2-amino-5-chloroisonicotinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C7H7ClN2O2

To a solution of methyl 2-amino-5-chloroisonicotinate (4.75 g, 25.5 mmol) in DMF (40 mL) was added 4-(dimethylamino)pyridine (0.466 g, 3.82 mmol), triethylamine (10.62 mL, 76 mmol), and di-tert-butyl dicarbonate (16.67 g, 76 mmol). The reaction was stirred at room temperature for 3 d. The reaction was quenched with water (40 mL). The aqueous layer was extracted with EtOAc (100 mL, three times), and the combined organic layers were washed with water, brine, dried (MgS04) and concentrated. The residue was purified by flash chromatography (80 g silica gel column, gradient elution from hexanes to 15% EtOAc/hexanes) to provide bis-Boc aminopyridine (6.36 g, 16.44 mmol) as a white powder.

With the rapid development of chemical substances, we look forward to future research findings about 1227002-03-0.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 944900-06-5, 2-Chloro-6-(trifluoromethyl)nicotinaldehyde, 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, SDS of cas: 944900-06-5, blongs to pyridine-derivatives compound. SDS of cas: 944900-06-5

General procedure: A mixture of 2-chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde 13 (19.0 g, 90.8 mmol), Ti(OEt)4 (41.4 g. 182 mmol), and (S)-(-)-tert-butylsulfinamide (11.2 g. 92.6 mmol) in THF (200 mL) was stirred at reflux for 5 h. The cooled reaction mixture was concentrated, and dissolved in ethylacetate (500 mL). The resulting suspension was filtered through a Celite pad, and the filtrate was concentrated and purified by column chromatography (hexane/ EtOAc = 4 : 1) to provide the imine (28.9 g) as a light yellow solid. A mixture of the imine (28.9 g, 92.5 mmol), allyl bromide (55.9 g, 0.46 mmol), and indium (42.5 g, 0.37 mmol) was vigorously stirred in sat. NaBraq at room temperature overnight. After addition of sat. NaHCO3 aq (500 mL), the reaction mixture was extracted with ethylacetate (250 mL x 3). The organic layers were filtered through a Celite pad, and dried (Na2SO4), concentrated and purified by column chromatography (hexane/ EtOAc = 1 : 4 with 5 % of Et3N) to provide 17 as a white solid (26.0 g, 77 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,944900-06-5, 2-Chloro-6-(trifluoromethyl)nicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Matsufuji, Tetsuyoshi; Shimada, Kousei; Kobayashi, Shozo; Kawamura, Asuka; Fujimoto, Teppei; Arita, Tsuyoshi; Hara, Takashi; Konishi, Masahiro; Abe-Ohya, Rie; Izumi, Masanori; Sogawa, Yoshitaka; Nagai, Youko; Yoshida, Kazuhiro; Takahashi, Hisashi; Bioorganic and Medicinal Chemistry Letters; vol. 24; 3; (2014); p. 750 – 755;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 184416-84-0, 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 184416-84-0 as follows.

Thionyl chloride (92 mul, 1.25 mmol) is added to a mixture of 2,3-dichloro-pyridine-4-carboxylic acid (200 mg, 1.04 mmol), DCM (2 ml) and DMF (20 mul). The mixture is heated to 100 C. for 10 minutes in a microwave. The mixture is concentrated in vacuo. DCM (2.5 ml) and 1,2-dimethylhydrazine dihydrochloride (207 mg, 1.55 mmol) is added before DIPEA (1.35 ml, 7.77 mmol) in DCM (2.5 ml) is added dropwise at RT. Stirring is continued for 1 hour. The mixture is diluted with DCM and extracted with water. The combined organic layers are dried over Na2SO4 and concentrated in vacuo. NMP (1 ml) and triethylamine (200 mul, 1.5 mmol) is added and the mixture heated to 190 C. for 25 minutes in a microwave. At RT water is added (500 mul) and the product purified by RP HPLC. Yield: 50 mg (24%). HPLC-MS: M+H=198; tR=0.44 min (METHOD-1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,184416-84-0, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; US2015/57286; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89694-10-0, Adding some certain compound to certain chemical reactions, such as: 89694-10-0, name is 2-Methoxy-3-methyl-5-nitropyridine,molecular formula is C7H8N2O3, 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 89694-10-0.

2-methoxy-3-methyl-5-nitropyridine (4.30 g; 25.57 mmol) and tert-butyl chioroacetate (4.50 mL; 31.37 mmol) in THF (60 mL) was stirred and cooled at -20C. Then potassium tert-butoxide (6.80 g; 60.60 mmol) was added portionwise to this mixture(temperature keep below -14C). After complete addition, this reaction was stirred at rt for 1 h. Water and an aqueous solution of HC1 3N were added and this mixture was extracted twice with EtOAc. The organic layer was decanted and the solvent was evaporated until dryness to give 7.35 g of intermediate 480 (100% yield).

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. 89694-10-0, 2-Methoxy-3-methyl-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (476 pag.)WO2017/125534; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem