Tag: M.W:100-200

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 97483-77-7, name is 5-Bromopicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 97483-77-7

To a stirred solution of 5-bromopicolinonitrile (10 g) in dry THE (150 mL) was added methylmagnesium bromide (20 mL, 3 M in THE) at -20C. After addition, the mixturewas allowed to warm to RT with stirring for 30 minutes. The reaction mixture was then treated with MeOH (200 mL) and NaBH4 (4 g). The reaction was stirred at RT for 15 hours and then poured into a solution of NaOH in water (200 mL, 1 M). The organic solvent was removed under reduced pressure and the aqueous phase was extracted with EA (100 mL x 3). The combined organic phase was washed with brine (50 mL) and dried over Na2SO4. After filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with DCM/MeOH = 99:1 to provide the subtitle compound. MS ESI: mlz = 201 [M+H].

With the rapid development of chemical substances, we look forward to future research findings about 97483-77-7.

Reference:
Patent; SANOFI; SCHWINK, Lothar; BUNING, Christian; GLOMBIK, Heiner; GOSSEL, Matthias; KADEREIT, Dieter; HALLAND, Nis; LOHMANN, Matthias; POeVERLEIN, Christoph; RITTER, Kurt; WO2015/150564; (2015); 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. 86873-60-1, name is 5-Chloro-2-picolinic acid, the common compound, a new synthetic route is introduced below. Safety of 5-Chloro-2-picolinic acid

A solution of 5-chloro-pyridine-2-carboxylic acid (0.136 g, 0.86 mmol) in dichloromethane (15 ml), was treated with Huenig’s base (0.30 ml, 1.73 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HATU) (0.328 g, 0.86 mmol) at room temperature. After 15 minutes of stirring, (RS)-5-(5-amino-2-fluoro-phenyl)-5-cyclopropyl-morpholine-3-thione (0.177 g, 0.66 mmol) was added and stirring continued for one hour. For the workup, the light yellow solution was poured on an ice-cold saturated solution of sodium hydrogen-carbonate, then extracted twice with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel using a 9:1-mixture of dichloromethane and ethyl acetate as the eluent. The 5-Chloro-pyridine-2-carboxylic acid [3-((RS)-3-cyclopropyl-5-thioxo-morpholin-3-yl)-4-fluoro-phenyl]-amide was obtained as an off-white solid (0.245 g, 90% of theory). Mass (calculated) C19H17ClFN3O2S [405.879]; (found) [M+H]+=406.

The synthetic route of 86873-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Andreini, Matteo; Banner, David; Guba, Wolfgang; Hilpert, Hans; Mauser, Harald; Mayweg, Alexander V.; Narquizian, Robert; Power, Eoin; Roger-Evans, Mark; Travagli, Massimiliano; Valacchi, Michela; Woltering, Thomas; Wostl, Wolfgang; US2011/46122; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 56622-54-9, 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. 56622-54-9, name is (6-Methylpyridin-3-yl)methanamine, molecular formula is C7H10N2, 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.

To a mixture of 5-(ethoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (1.5 g, 5.3 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (2.0 g, 10 mmol), 1- hydroxybenzotriazole hydrate (0.32 g, 2.1 mmol), and CH2Cl2 (50 mL) were added (6-methylpyridin-3- yl)methanamine (0.97 g, 7.9 mmol) and NN-diisopropylethylamine (1.8 mL, 10 mmol). The mixture was stirred at room temperature for 4h, and then washed with water and aq. Na2CO3 solution, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel column to afford a white foam. LC-MS: 389.4 [M+l]+; 1H NMR (400 MHz, CDCl3): 8.53 (d, IH, J = 2.0 Hz), 8.39 (t, IH, J = 1.6 Hz), 8.29 (t, IH, J = 1.6 Hz), 8.26 (t, IH, J = 1.6 Hz), 7.66 (dd, IH, J = 8.0, 2.0 Hz), 7.55 (d, 2H, J = 8.4 Hz), 7.28 (d, 2H, J = 8.0 Hz), 7.17 (d, IH, J = 8.0 Hz), 6.64 (m, IH), 4.67 (d, 2H, J = 5.6 Hz), 4.42 (q, 2H, J = 7.2 Hz), 2.57 (s, 3H), 2.41 (s, 3H), 1.42 (t, 3H, J = 7.2 Hz).

According to the analysis of related databases, 56622-54-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RENOVIS, INC.; WO2009/110985; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156270-06-3, 1H-Pyrrolo[2,3-b]pyridine-3-carboxylicacid, 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, Application In Synthesis of 1H-Pyrrolo[2,3-b]pyridine-3-carboxylicacid, blongs to pyridine-derivatives compound. Application In Synthesis of 1H-Pyrrolo[2,3-b]pyridine-3-carboxylicacid

General procedure: Respective benzoic acid derivatives 5-chloro-2-methoxybenzoic acid or 13a-h (1 eq) were dissolved in anhydrous DMF, then EDCI (1.5eq), HOBT (1.5 eq) and DIEA (2.0 eq) were added successively. After the mixture was stirred at room temperature for 0.5?1h, the respective amine derivatives 3, 6 or 10 (1 eq) were added. The reaction mixture was stirred at room temperature overnight (or 12h). After the TLC showed the disappearance of the starting materials, water was added and the resulting suspension was filtered using a buchner funnel, and the precipitate was washed with water and then dried to give white solid powder. Products were further purified by flash column chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156270-06-3, 1H-Pyrrolo[2,3-b]pyridine-3-carboxylicacid, and friends who are interested can also refer to it.

Reference:
Article; Yuan, Zigao; Sun, Qinsheng; Li, Dan; Miao, Shuangshuang; Chen, Shaopeng; Song, Lu; Gao, Chunmei; Chen, Yuzong; Tan, Chunyan; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 281 – 292;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 100367-39-3, 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. 100367-39-3, name is 4-Bromo-2-methoxypyridine, molecular formula is C6H6BrNO, 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.

4-BromoBromo-2-methoxypyridine (3.06 g, 16.2 mmol), (6- (trifluoromethyl)pyridin-3-yl)methanol (2.74 g, 15.5 mmol), 3,4,7,8- tetramethylphenanthroline (0.36 g, 0.15 mmol), CuI (0.14 g, 0.74 mmol) and Cs2CO3 (7.57 g, 23.2 mmol) were combined in toluene (15 mL) and heated to reflux under a nitrogen Attorney’s Docket 2882.023B atmosphere for 16 h. Upon cooling the mixture was purified by flash column chromagraphy (silica gel, hexanes/EtOAc, 1 :0 to 1 :1) to provide the title compound (3.19 g, 72%) as a red oil: 1H NMR (300 MHz, CDCl3) delta 8.78 (s, IH), 8.02 (d, J= 5.9 Hz, IH), 7.95 (d, J= 8.1 Hz, IH), 7.32 (d, J= 8.0 Hz, IH), 6.55 (dd, J= 5.9, 2.2 Hz, IH), 6.26 (d, J = 2.2 Hz, IH), 5.16 (s, 2H), 3.93 (s, 3H).

According to the analysis of related databases, 100367-39-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; WO2009/89482; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1101120-05-1, 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. 1101120-05-1, name is 3-Formylpyrazolo[1,5-a]pyridine-5-carbonitrile, molecular formula is C9H5N3O, 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.

General procedure: These were made using NaHCO3 or 2,6-lutidine as detailed below, unless otherwise stated. Methylhydrazine sulfate (1.2 equiv) and NaHCO3 (5 equiv) were added to a solution of 3-formylpyrazolo[1,5-a]pyridine-5-carbonitrile (2) (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The solvent was removed in vacuo and the residue taken up in CH2Cl2 and water. The layers were separated and the aqueous phase extracted with CH2Cl2, then the combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography or trituration then afforded the hydrazides. Alternatively, methylhydrazine sulfate (1.2 equiv) and 2,6-lutidine (5 equiv) were added to a solution of 2 (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The hydrazide was then filtered off, washed with MeOH and dried.

According to the analysis of related databases, 1101120-05-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kendall, Jackie D.; Giddens, Anna C.; Tsang, Kit Yee; Frederick, Raphael; Marshall, Elaine S.; Singh, Ripudaman; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 58 – 68;,
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.106984-91-2, name is 6-Oxo-1,6-dihydropyridine-3-carbaldehyde, molecular formula is C6H5NO2, molecular weight is 123.11, as common compound, the synthetic route is as follows.Recommanded Product: 6-Oxo-1,6-dihydropyridine-3-carbaldehyde

Example 22: [Show Image] To a solution of intermediate 22b (295 mg, 0.720 mmol) in acetonitrile (20 mL) and acetic acid (200 muL) was added 6-hydroxynicotinaldehyde (87 mg, 0.708 mmol). The reaction mixture was stirred vigorously at reflux temperature overnight. The solvent was removed under reduced pressure. The crude product was purified by preparative LC-MS. The pure product (54 mg, orange oil) was dissolved in methanol (2 mL) and 1 M HCl in diethyl ether (110 muL, 0.110 mmol) was added. The solvents were removed under reduced pressure. The product was taken up in water (3 mL) and lyophilized.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,106984-91-2, 6-Oxo-1,6-dihydropyridine-3-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Santhera Pharmaceuticals (Schweiz) AG; EP2439197; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 57266-69-0, 3-Chloropicolinic acid, 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, 57266-69-0, blongs to pyridine-derivatives compound. Quality Control of 3-Chloropicolinic acid

To a solution of 3-chloropyridine-2-carboxylic acid (2.1 g, 13.33 mmol, 1.00 equiv) in THF (40 mL) was added Et3N (2.7 g, 26.68 mmol, 2.00 equiv), followed by the addition of chloro(propan-2-yloxy)methanone (2.45 g, 19.99 mmol, 1.50 equiv) dropwise with stirring at 0 C. The solution was strried for 1 h at room temperture. The solid was removed by filtration. To the filtrate was added NaBH4 (1.53 g, 40.44 mmol, 3.00 equiv). The resulting solution was stirred for 2 h at rt, then diluted with 50 mL of H2O and extracted with 2*100 mL of EtOAc. The combined organic layers were washed with 50 mL of saturated Nacl, dried over Na2SO4, concentrated under vacuum, and purified with silica gel chromatography using with EtOAc/petroleum ether (1:6) to afford 0.9 g (47%) of the title compound as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57266-69-0, its application will become more common.

Reference:
Patent; Vettore, LLC; PARNELL, Kenneth Mark; MCCALL, John; ROMERO, Donna; (172 pag.)US2018/162822; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 16063-70-0 ,Some common heterocyclic compound, 16063-70-0, molecular formula is C5H2Cl3N, 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 30.74 g of potassium tert-butoxide in 100 ml of dimethylsulfoxide, 16.72 g of nitromethane was added dropwise with stirring under cooling with ice, and after the addition, the mixture was stirred at room temperature for another 1 hour. Then, the reaction mixture was cooled with ice again, and to the reaction mixture, 25.00 g of 2,3,5-trichloropyridine in 100 ml of dimethylsulfoxide was added dropwise with stirring, and after the addition, the mixture was stirred at 70C for another 6 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, poured into 200 ml of 10% aqueous hydrochloric acid with stirring under cooling with ice and extracted with ethyl acetate (200 ml*1). The resulting organic layer was washed with water (100 ml*1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 5:95 to 10:90) as the eluent to obtain 10.10 g of the desired product as a pale yellow oil. 1H NMR (CDCl3, Me4Si, 300MHz) delta8.53 (d, J=2.4Hz, 1 H), 7.84 (d, J=2.4Hz, 1 H), 5.76 (s, 2H).

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. 16063-70-0, 2,3,5-Trichloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nissan Chemical Industries, Ltd.; IWASA, Motoyoshi; TSUJI, Keisuke; TOMIZAWA, Mitsutaka; MITA, Takeshi; KUWAHARA, Hidehito; ASAHI, Miho; IMANAKA, Hotaka; EP2873658; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 609-71-2, 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. 609-71-2, name is 2-Oxo-1,2-dihydropyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below.

Step 1 Methyl 2-hydroxynicotinate 2-Hydroxynicotinic acid (2.50 g, 17.97 mmol) was dissolved in methanol (20.00 mL), added with sulfuric acid (18M, 47.90 uL), and then stirred at 70 C. under nitrogen atmosphere for 12 hours. After the reaction mixture was concentrated, the residue was dissolved in dichloromethane (50.00 mL) and the system was adjusted to pH=8 with saturated sodium bicarbonate solution. A white solid was slowly precipitated and filtered to give methyl 2-hydroxynicotinate (a white solid, 1.5 g, yield: 54.51%). 1H NMR (400 MHz, CDCl3) 8.27 (dd, J=2.0, 7.0 Hz, 1H), 7.78 (dd, J=2.0, 6.0 Hz, 1H), 6.41 (t, J=6.8 Hz, 1H), 3.90 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,609-71-2, 2-Oxo-1,2-dihydropyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Heilongjiang Zhenbaodao Pharmaceutical Co., Ltd.; MEDSHINE DISCOVERY INC.; HE, Haiying; JIANG, Zhigan; XIA, Jianhua; WANG, Jing; HAN, Lixia; LAN, Lihong; ZHOU, Hui; LAI, Kunmin; CHEN, Shuhui; US2018/346438; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem