Tag: M.W:100-200

Reference of 136888-17-0, 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. 136888-17-0, name is 5-Chloro-1H-pyrrolo[2,3-c]pyridin-2(3H)-one, molecular formula is C7H5ClN2O, 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.

C. 5-Chloro-3-(2-thenoyl)-6-azaoxindole Pellets of sodium metal (232 mg, 10 mmol) were added to dry ethanol (10 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid 5-chloro-6-azaoxindole (340 mg, 2.0 mmol) was added followed by ethyl 2-thiophenecarboxylate (0.54 mL, 4.0 mmol). The mixture was heated under nitrogen at reflux overnight during which a precipitate formed. The mixture was cooled, poured into ice/water and acidified to pH 4 with 6N HCl solution. The solid product (475 mg) was collected by filtration, washed with water, and dried in the air. This material was recrystallized from methanol to afford the title compound (190 mg, 34%). 1 H NMR (DMSO-d6): delta10.62 (br s, 1H), 8.79 (d, J=3.2 Hz, 1H), 7.92 (s, 1H), 7.77 (d, J=5 Hz, 1H), 7.65 (s, 1H), 7.17-7.14 (m, 1H).

According to the analysis of related databases, 136888-17-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US5811432; (1998); A;,
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. 145335-90-6, name is Imidazo[1,2-a]pyridine-8-carboxylic acid hydrochloride, the common compound, a new synthetic route is introduced below. Safety of Imidazo[1,2-a]pyridine-8-carboxylic acid hydrochloride

Step B: Preparation of Imidazo[l,2-alpha]pyridine-2-carbonyl chloride Hydrochloride. Method 1: To imidazo[l,2-alpha]pyridine-8-carboxylic acid hydrochloride (10.0 g, 50.4 mmol), thionyl chloride (98 g, 60 mL, 822 mmol) was added. To the resulting mixture N,N- dimethylformamide (1.6 mL) was added. Gas evolution was noticed and the reaction mixture was heated to 50 0C overnight (18 h). The reaction mixture was then cooled to room temperature and the product was filtered and washed with isopropyl acetate (40 mL) followed by 10% isopropanol in isopropyl acetate (40 mL). The white solid thus obtained was dried under reduced pressure to afford the title compound (10.2 g, 93%). The compound was used without further purification in Step E.

The synthetic route of 145335-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARENA PHARMACEUTICALS INC.; WO2009/23253; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 129432-25-3, 2,6-Dichloro-4-methylpyridin-3-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, 129432-25-3, blongs to pyridine-derivatives compound. SDS of cas: 129432-25-3

To a mixture of 2,6-dichloro-4-methylpyridin-3-amine (0.500 g, 2.82 mmol) and potassium thiocyanate (0.823 g, 8.47 mmol) in ethanol (7.5 mL) at rt was added concentrated hydrochloric acid (10.04 mL, 330 mmol) dropwise. The mixture was heated at 100 C for 44 h. Additional potassium thiocyanate (0.823 g, 8.47 mmol) was added and the mixture was heated at 100 C for additional 31 h. The reaction mixture was concentrated under vacuum to dryness. To the residue was added 1 N NaOH solution (10 mL), followed by solid K2CO3, until the mixture became basic (pH = 9-10). The mixture was extracted with dichloromethane (4 x 40 mL). The combined extracts were dried over anhydrous Na2S04, filtered, and concentrated under vacuum. The residue was purified by flash chromatograph (80 g silica gel, solid loading, 0-6% methanol/dichloromethane) to provide 5-chloro-7-methylthiazolo[5,4-b]pyridin-2-amine (0.331 g, 1.658 mmol, 58.7 % yield) as a tan solid. MS (ESI) m/z: 199.9 [M+H]+; NMR (500 MHz, DMSO-de) delta 7.90 (s, 2H), 7.22 (s, 1H), 2.41 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,129432-25-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; FENG, Jianxin; LIU, Chunjian; HUANG, Yanting; (130 pag.)WO2019/89665; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 121643-44-5, 2-Methoxy-3-(trifluoromethyl)pyridine, 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, 121643-44-5, blongs to pyridine-derivatives compound. COA of Formula: C7H6F3NO

Intermediate 1 5-Bromo-2-methoxy-3-trifluoromethyl-pyridine To 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 113.0 mmol) and 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 mL) and the resulting mixture stirred at rt for 18 h under argon. The TFA was removed in vacuo (50 mbar, 45 C.) and the residue suspended in tert-butyl methyl ether (200 mL). The resulting colourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL). The filtrate was concentrated in vacuo, diluted with heptane/tert-butyl methyl ether (5/1, 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane/EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHCO3 (20 g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5 g, 74% yield). 1H-NMR (400 MHz, DMSO-d6, 298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1H) 8.4 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,121643-44-5, its application will become more common.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; US2015/342951; (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. 5444-01-9, name is 4-Methylnicotinonitrile, the common compound, a new synthetic route is introduced below. Recommanded Product: 4-Methylnicotinonitrile

Preparation of Intermediate methyl 2-(3-cyanopyridin-4-yl)acetate (I-65a) 1M LiHMDS (45 mL, 44.794 mmol) was added to a solution of 4-methylnicotinonitrile (2.52 g, 21.33 mmol) in THF (15 mL) at -78 C. and the resulting reaction mass was stirred at -78 C. for 1 hour. This was followed by the addition of dimethyl carbonate (1.98 mL, 23.464 mmol) and stirred the resulting reaction mass at -78 C. for 1 hour and further at 0 C. for 2 hours. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mass was quenched with saturated NH4Cl solution and extracted using ethyl acetate. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (25% ethyl acetate in hexane) afforded 530 mg of the product (14.10% yield). 1H NMR (300 MHz, CDCl3): delta 8.9 (s, 1H), 8.79 (d, 1H), 7.4 (d, 1H), 3.9 (s, 2H), 3.79 (s, 3H)

The synthetic route of 5444-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; Bock, Mark Gary; Gaul, Christoph; Gummadi, Venkateshwar Rao; Moebitz, Henrik; Sengupta, Saumitra; US2014/45872; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 143803-93-4 ,Some common heterocyclic compound, 143803-93-4, molecular formula is C9H8N2O2, 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.

General procedure: These were made by decarboxylation/Vilsmeier or hydrolysis/reduction/reoxidation as detailed below, unless otherwise stated.Decarboxylation was carried out by refluxing a solution of the ester (1 equiv) in 40% aqueous H2SO4 (3 mL) for 18 h. The solution was then cooled in ice and neutralised to pH 7 with 6 M NaOH, then extracted twice with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo to leave the decarboxylated material. The pyrazolo[1,5-a]pyridine was then reacted under Vilsmeier conditions in dry DMF (2 mL) with POCl3 (3 equiv) at 0 C under an atmosphere of N2. The reaction mixture was then warmed to room temperature and stirred for 2 h. The solution was poured onto ice, basified to pH 10 with 1 M NaOH, stirred for 1 h then extracted twice with CH2Cl2. The combined extracts were washed twice with water, dried (Na2SO4) and the solvent removed in vacuo to leave the aldehyde.Alternatively, the ester was hydrolysed by refluxing a solution of the ester (1 equiv) in 1 M NaOH (3 equiv) and EtOH (5 mL) for 6 h. The EtOH was removed in vacuo, and then the aqueous residue acidified to pH 1 with 1 M HCl. The precipitated carboxylic acid was filtered off, washed with water and dried. The carboxylic acid was reduced by adding CDI (1.5 equiv) to a suspension of carboxylic acid (1 equiv) in dry THF (10 mL) under an atmosphere of N2. After stirring for 18 h, the resulting solution was added dropwise to a solution of NaBH4 (5 equiv) in H2O (10 mL) and stirred for 30 min. The reaction was then quenched by the addition of 1 M HCl and stirred for a further 30 min. The solution was neutralised with saturated aqueous NaHCO3 and extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with a hexanes: EtOAc gradient) gave the alcohol. Reoxidation was carried out by stirring a suspension of the pyrazolo[1,5-a]pyridine-3-methanol (1 equiv) and MnO2 (10 equiv) in CH2Cl2 (2 mL) at room temperature for 4 days. The reaction mixture was then filtered through celite, washed with CH2Cl2, and the solvent removed from the filtrate in vacuo to leave the aldehyde.

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. 143803-93-4, 4-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; 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. 69 – 85;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 823-61-0 ,Some common heterocyclic compound, 823-61-0, molecular formula is C7H10N2, 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 solutionof 26-S3 (170 mg, 0.44 mmol) and 6-methylpyridin-2-amine (90 mg, 0.48 mmol) in DCE (5 mL) were added DIPEA (0.29 mL, 1.76 mmol) and EEDQ (217 mg, 0.88 mmol). The reaction mixture was stirred at 90 C overnight and concentrated under high vacuum. The remaining residue was purified by column chromatography on silica gel (eluted with PE/EtOAc = 4:1) to afford 26-S4(103 mg, 41% yield) as a yellow solid. LC/MS (ESI) m/z: 555/557 (M+H)t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,823-61-0, its application will become more common.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; BARRISH, Joel, Charles; GREENLEE, William; EASTMAN, Kyle, J.; (0 pag.)WO2018/160889; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 92992-85-3, 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. 92992-85-3, name is 2-Bromo-3,5-dimethylpyridine. A new synthetic method of this compound is introduced below.

To a mixture of (R)-2-methylpiperazine-1-carboxylic acid tert-butyl ester (1 g),2-bromo-3,5-dimethylpyridine (975 mg),tris(dibenzylideneacetone)dipalladium(O)(92 mg),rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (125 mg) and tert-butoxy sodium (650 mg) was added toluene (17 mL) and the mixture was stirred under microwave irradiation at 130c for 2 hr. The reaction mixture was purified by column chromatography (hexane:ethyl acetate)to give the title compound (220 mg). MS (ESI)m/z: 306(M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,92992-85-3, 2-Bromo-3,5-dimethylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 131747-55-2, Adding some certain compound to certain chemical reactions, such as: 131747-55-2, name is 2-Fluoro-3-(hydroxymethyl)pyridine,molecular formula is C6H6FNO, 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 131747-55-2.

At 0C, 55% sodium hydride 0.70 g (16 mmol) was added in portions to a THF (20 mL) solution of (2-fluoropyridin-3-yl)methanol 1.3 g (10 mmol) synthesized in the same manner as in Reference Example 52 and iodomethane 6.6 mL (110 mmol), and the mixture was stirred at room temperature for 2 hours. After the completion of the reaction, water was added to the reaction mixture, and followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (eluting solvent: hexane:ethyl acetate) to give the title compound 0.89 g (6.3 mmol, yield 63%) as a colorless oil. 1H-NMR spectrum (400MHz, DMSO-d6) delta:8.23 – 8.14 (m, 1H), 8.02 – 7.92 (m, 1H), 7.40 – 7.35 (m, 1H), 4.46 (s, 2H), 3.33 (s, 3H).

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. 131747-55-2, 2-Fluoro-3-(hydroxymethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UBE Industries, Ltd.; KOMORI, Ken-ichi; NINOMIYA, Akishi; USHIYAMA, Shigeru; SHINOHARA, Masaru; ITO, Koji; KAWAGUCHI, Tetsuo; TOKUNAGA, Yasunori; KAWADA, Hiroyoshi; YAMADA, Haruka; SHIRAISHI, Yusuke; KOJIMA, Masahiro; ITO, Masaaki; KIMURA, Tomio; (432 pag.)EP3333163; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 688782-02-7, 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. 688782-02-7, name is 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7ClN2, 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 97(1)4-Chloro-3-methyl-1-{(2-(trimethylsilyl)ethoxy)methyl}-1H-pyrrolo[2,3-b]pyridine (97a)Compound (40d) (1.0 g) was dissolved in DMF (20 mL), and sodium hydride (0.288 g, a 55% dispersion in paraffin liquid) was added to the resulting solution at 0 C., followed by stirring for 10 min. Then, {2-(chloromethoxy)ethyl}silane (1.16 mL) was added to the reaction solution, followed by stirring at room temperature for 1 hr. Ice water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and was then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate) to obtain compound (97a) (4.50 g, 84%) as a colorless oily substance.1H-NMR (CDCl3) delta: 8.21 (1H, d, J=5.12 Hz), 7.19 (1H, s), 7.10 (1H, d, J=5.12 Hz), 5.68 (2H, s), 3.58 (2H, t, J=8.17 Hz), 2.43 (3H, s), 0.97 (2H, t, J=8.17 Hz), 0.00 (9H, s); LRMS (ESI) m/z 297 [M+H]+.

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 688782-02-7, 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; US2012/108589; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem