Month: April 2022

Electric Literature of 112193-41-6, 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. 112193-41-6, name is 5-Bromonicotinohydrazide, molecular formula is C6H6BrN3O, 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 102 4-[1-(3-Aminopropyl)-5-fluoro-indol-3-yl]-5-(5-bromo-pyridin-3-yl)-2,4-dihydro-[1,2,4]triazol-3-one hydrochloride The title compound was prepared by the method described in Example 45 starting from the product of Example 45d) and 5-bromo-nicotinic acid hydrazide. 1H NMR (400 MHz, DMSO-d6): delta12.45 (1H, s); 8.68 (1H, d); 8.48 (1H, d); 8.00 (1H, m); 7.89 (3H, bs); 7.80 (1H, s); 7.70 (1H, m); 7.16 to 7.09 (2H, m); 4.35 (2H, m); 2.75 (2H, m); 2.04 (2H, m). APCI-MS m/z: 431 [MH+].

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 112193-41-6, 5-Bromonicotinohydrazide.

Reference:
Patent; Astrazeneca AB; US6492406; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1018505-59-3, 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 1018505-59-3 as follows.

To a solution of 3-chloro-7-(2, 6-dichloro-3, 5-dimethoxyphenyl) isoqinoline (600 mg, 1.628 mmol), 5-(4-ethylpiprazine-l-yl) pyridine-2-amine (step 3.1) (376 mg, 1.82 mmol), X-Phos (77.60 mg, 10 mol %) and cesium carbonate (1.06 g, 1.25 mmol) in Toluene (15 mL) and t- BuOH (5 mL) (4: 1) argon was purged for 20 min. Then was added Pd2 (dba)3 (149 mg, 10 mol %) again argon was purged for 5 min. The reaction mixture was heated at 120C overnight. The reaction mixture was cooled to room temperature and filtered through celite pad and filtrate was concentrated under reduced pressure. Product was purified by column chromatography on silica gel column using DCM: MeOH: NH3 aq. (95:5: 1%) as an eluent to afford 7-(2, 6-dichloro-3, 5-dimethoxyphenyl)-N-[5-(4-ethylpiperazin-l-yl) pyridin-2-yl] isoquinoline-3 -amine (600 mg) as a pale yellow solid. 1H NMR (400 MHz, CDC13) delta 8.97 (s, 1H), 8.09 (dd, J = 25.7, 7.3 Hz, 2H), 7.82 – 7.68 (m, 2H), 7.41 (dd, J = 8.5, 1.6 Hz, 1H), 7.32 (dd, J = 8.9, 2.9 Hz, 1H), 7.17 – 7.10 (m, 1H), 6.65 (s, 1H), 3.99(s, 6H), 3.26 – 3.16 (m, 4H), 2.71 – 2.62 (m, 4H), 2.51 (q, J = 7.2 Hz, 2H), 1.15 (t, J= 7.2 Hz, 3H). M/Z: 537.1, M+l : 538.6, tR= 0.81 min. (System 1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1018505-59-3, its application will become more common.

Reference:
Patent; EVOTEC (UK) LTD.; MC CARTHY, Clive; MILLS, Matthew; WO2014/44846; (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. 190271-88-6, name is Methyl 2-chloro-5-nitronicotinate, molecular formula is C7H5ClN2O4, 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. Recommanded Product: Methyl 2-chloro-5-nitronicotinate

2-Chloro-5-nitro-nicotinic acid methyl ester (578 mg, 2.44 mmol) and n-propyl hydrazine oxalate (400 mg, 2.44 mmol) in DMF (10 ml) was treated with K2CO3 (672 mg, 4.87 mmol). The mixture was stirred at 80 C. for 3 hr and then at RT overnight. The reaction mixture was then concentrated and diluted with EtOAc. The organic layer was partitioned over water and solid citric acid was added to acidify the mixture to pH 1. The organic layer was washed with brine, dried over Na2SO4 and concentrated to dryness. The solid obtained was triturated with CH2Cl2 and then hexanes to afford the product, 5-nitro-1-propyl-1,2-dihydro-pyrazolo[3,4-b]pyridin-3-one (405 mg, Yield: 75%). LCMS calcd for C9H10N4O3 (m/e) 222, obsd. 223 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 190271-88-6.

Reference:
Patent; Bolin, David Robert; Cai, Jianping; Cheung, Adrian Wai-Hing; Goodnow, JR., Robert Alan; Hamilton, Matthew Michael; Li, Shiming; McDermott, Lee Apostle; Yun, Weiya; US2009/76275; (2009); 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. 1079179-12-6, name is 2-Chloro-3-fluoro-5-nitropyridine, molecular formula is C5H2ClFN2O2, 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. name: 2-Chloro-3-fluoro-5-nitropyridine

To the reaction mixture of crude Compound 131 above was added 2- chloro-3-fluoro-5-nitropyridine (6 eq, 412 mg, 2.34 mmol) and CS2CO3 (6 eq, 763 mg, 2.34 mmol). The mixture was stirred at room temperature overnight and then partitioned between water and EtOAc. The organic phase was washed with aq saturated NaCl and concentrated. The residue was purified by silica gel column to give Compound 132.

With the rapid development of chemical substances, we look forward to future research findings about 1079179-12-6.

Reference:
Patent; EXELIXIS, INC.; BANNEN, Lynne Canne; BUI, Minna; JIANG, Faming; WANG, Yong; XU, Wei; (235 pag.)WO2019/148043; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 59290-81-2, 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. 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid. A new synthetic method of this compound is introduced below.

A solution of 2-methyl-5-nitronicotinic acid 1 (50 mg, 0.27 mmol), intermediate III (90 mg, 0.41 mmol), PyBOP (281 mg, 0.54 mmol) and DIEA (0.14 ml, 0.81 mmol) in DCM/DMF (6 ml, 5:1) was stirred at 20C for 16 hr. The mixture was washed with sat. aq. NaHCO3, H2O, dried over MgSO4, evaporated and the brown residue was chromatographed on reverse phase HPLC (10-95% AcN in H2O) to give 8 (100 mg) as a brown solid. (Calculated mass: 386.4, observed mass: 386.5).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59290-81-2, 2-Methyl-5-nitro-3-pyridinecarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; KEMIA, INC.; WO2007/56016; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69422-72-6, Adding some certain compound to certain chemical reactions, such as: 69422-72-6, name is 2,4,6-Trichloronicotinic acid,molecular formula is C6H2Cl3NO2, 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 69422-72-6.

A solution of the product of EXAMPLE 1 1C (1.5 g,6.7 mmol) in dichloromethane (50 mL) was treated at room temperature with 2 drops ofN,N-dimethylformamide. Oxalyl chloride (1.27 g, 10 mmol) was added dropwise over 15 minutes and stirring was continued for 2 hours. The solution was concentrated and dried under vacuum to give the crude acid chloride. Ammonium (gas) was passed through a solution of the acid chloride in tetrahydrofuran (20 mL) and the mixture stirred at room temperature for 0.5 hours. The mixture was concentrated under vacuum and the residue purified by flash chromatography on silica gel (200-3 00 mesh) eluting with 100/1 dichloromethane/methanol to give the title compound. MS: 225 (M+H).

According to the analysis of related databases, 69422-72-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; Vasudevan, Anil; Penning, Thomas Dale; Chen, Huanming; Liang, Bo; Wang, Shaohui; Zhao, Zhongqiang; Chai, Dikun; Yang, Leifu; Gao, Yingxiang; Pliushchev, Marina; US2014/171429; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19230-59-2, 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 19230-59-2, name is 2-Methoxy-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

(lb) 2-Methoxy-3-methyl-5-nitropyridine [Formula 9]; Concentrated sulfuric acid (5 ml) and fuming nitric acid (5 ml) were added to 2-methoxy-3- methylpyridine (1.61 g, 13.1 mmol) under ice cooling, and stirred at 0C for 1 hour and further stirred at room temperature overnight. The reaction mixture was poured onto ice, neutralized with ammonia solution, extracted with ethyl acetate, dried over magnesium sulfate, the solvent was evaporated, thereby yielding the title compound (1.63 g, 9.71 mmol, and 74%). ¹H NMR(400MHz, DMSO-d6) 8 ppm; 2.25(3H, s), 4.04(3H, s), 8.37-8.40(lH, m), 8.92-8.95 (1H, m).

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 19230-59-2, 2-Methoxy-3-methylpyridine.

Reference:
Patent; EISAI CO., LTD.; WO2005/103049; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 184416-84-0, 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.184416-84-0, name is 2,3-Dichloroisonicotinic acid, molecular formula is C6H3Cl2NO2, molecular weight is 192, as common compound, the synthetic route is as follows.

Thionyl chloride (92 mu, 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 mu). The mixture is heated to 100C 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 Na2S04 and concentrated in vacuo. NMP (1 ml) and triethylamine (200 mu, 1.5 mmol) is added and the mixture heated to 190C for 25 minutes in a microwave. At RT water is added (500 mu) and the product purified by RP HPLC. Yield: 50 mg (24%). HPLC-MS: M+H=198; tR=0.44 min (METHOD l).

Statistics shows that 184416-84-0 is playing an increasingly important role. we look forward to future research findings about 2,3-Dichloroisonicotinic acid.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; WO2015/25018; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 116986-09-5, Adding some certain compound to certain chemical reactions, such as: 116986-09-5, name is Methyl 3-(bromomethyl)picolinate,molecular formula is C8H8BrNO2, 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 116986-09-5.

To a solution of S-[(6-chloro-4-methyl-3-pyridyl) methyl] ethanethioate (1.67 g, 7.8 mmol) in 50 mL methanol was added K2CO3 (2.14 g, 15.5 mmol). The mixture was stirred for 30 min at room temperature. Then methyl-(3-bromomethyl)pyridine-2-carboxylate (1 .78 g, 7.8 mmol) was added and it was stirred for 2.5 hours at room temperature. The mixture was concentrated to give the crude product (2.87 g, crude, MS+1 =322).

According to the analysis of related databases, 116986-09-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; BASF SCHWEIZ AG; WITSCHEL, Matthias; KRAUS, Helmut; HUTZLER, Johannes; NEWTON, Trevor William; REINGRUBER, Ruediger; FRASSETTO, Timo; PARRA RAPADO, Liliana; BESONG, Gilbert; RACK, Michael; KLOET, Andree van der; SEITZ, Thomas; LERCHL, Jens; KREUZ, Klaus; PASTERNAK, Maciej; EVANS, Richard Roger; WO2013/178585; (2013); 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. 72600-67-0, name is 2-Chloro-3-fluoro-5-(trifluoromethyl)pyridine, molecular formula is C6H2ClF4N, 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. COA of Formula: C6H2ClF4N

(c) 47.7 g (0.82 mol) of potassium fluoride and 10.0 g (0.065 mol) of caesium fluoride are suspended in 300 ml of sulfolane and the suspension is heated to 140 C. 60 ml of sulfolane are distilled off by decreasing the pressure and subsequently 65.6 g (0.329 mol) of 2-chloro-3-fluoro-5-trifluoromethylpyridine and 1.3 g (0.004 mol) of 18-crown-6 are added. The reaction mixture is stirred for 48 hours at 140 C. and subsequently distilled by introducing steam. The oil is separated and the aqueous phase is extracted twice with a small amount of ether. The organic phases are purified, dried with a small amount of magnesium sulfate and filtered. Distillation affords 54.8 g (91% of theory) of 2,3-difluoro-5-trifluoromethylpyridine, b.p. 100-102 C. (980 mbar).

With the rapid development of chemical substances, we look forward to future research findings about 72600-67-0.

Reference:
Patent; Ciba-Geigy Corporation; US4831148; (1989); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem