Tag: M.W:100-200

Electric Literature of 1137-67-3, Adding some certain compound to certain chemical reactions, such as: 1137-67-3, name is 2-(Pyridin-3-yl)-1H-benzo[d]imidazole,molecular formula is C12H9N3, 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 1137-67-3.

, weighing 0.25g cobalt chloride hexahydrate,0.2 g of 2- (3-pyridyl) benzimidazole,0.2 g of 1,3-benzenedicarboxylic acid and 15 mL of water in a 50 mL flask,The flask was placed on a magnetic stirrer and stirred for 30 minutes.(2)The mixed homogeneous solution was transferred to a 25 mL autoclave.,The autoclave was placed in an oven,Heated from room temperature to 170 C at a rate of 1 C / min,At this temperature for 72h,And then to 5 / h rate down to room temperature,Solid-liquid separation is shown in Figure 1-3,The dinuclear cobalt complex shown in Figures 4-6,The yield was about 65%.

According to the analysis of related databases, 1137-67-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Heifei University; Zhang, Quanzheng; Cheng, Xuan; Ding, Dong; Chen, Ying; (13 pag.)CN103923126; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 36953-37-4, 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 36953-37-4, name is 4-Bromopyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Example 26i 4-Bromo-2-(difluoromethoxy)pyridine 4-Bromopyridin-2(1H)-one (200 mg, 1.15 mmol) and sodium 2-chloro-2,2-difluoroacetate (210 mg, 1.38 mmol) were slurried in dry acetonitrile (8 mL). The mixture was refluxed overnight, allowed to cool to r.t. and directly extracted with pentane (3*5 mL). The combined organic phases were evaporated to give 219 mg (85% yield) of the title compound: 1H-NMR (500 MHz DMSO-d6) delta 8.18 (d, 1H), 7.70 (t, 1H), 7.56 (d, 1H), 7.50 (s, 1H); MS (CI+) m/z 226 224 [M+1]+

According to the analysis of related databases, 36953-37-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; US2010/125087; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 95652-80-5, 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 95652-80-5 as follows.

To a stirred solution of 31(6.83 g, 30.7 mmol) in THF (120 mL) was added i-PrMgCl·LiCl (ca.1.0 Msolution in THF, 32.2 mL, 32.2 mmol) at -20C. After 2 h, DMF (7.2 mL, 92.1 mmol) was added dropwise at -20C. The resulting mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material including 12was applied to the following reaction without further purification.To a suspension of the crude material including 12and NaOAc (3.78 g, 46.1 mmol) in the 1 : 1 mixture of n-BuOH and toluene (total 120 mL) was added Pd(dppf) Cl2 (1.12 g, 1.54 mmol) at room temperature. The resulting mixture was stirred under ordinary CO pressure (balloon) at 100C for 18 h. The reaction was quenched with saturated aqueous NH4Cl, filtered through a pad of Celite and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, n-hexane-EtOAc=2 : 1) to afford 13(4.75 g, 65% 2 steps) as a yellow oil.13: IR (film, cm-1): 2963, 2876, 1721, 1692, 1595, 1481, 1337, 1277, 1261, 1219, 1138, 1072, 1022; 1H-NMR (CDCl3, 500 MHz) delta: 10.39 (s, 1H), 8.18 (d, J=8.50 Hz, 1H), 6.94 (d, J=8.50 Hz, 1H), 4.44 (t, J=6.80 Hz, 2H), 4.06 (s, 3H), 1.83-1.76 (m, 2H), 1.54-1.45 (m, 2H), 0.99 (t, J=7.37 Hz, 3H); 13C-NMR (CDCl3, 125 MHz) delta: 189.1, 166.1, 165.2, 150.7, 138.6, 125.9, 114.1, 66.3, 54.5, 30.5, 19.2, 13.7; HR-MS (ESITOF): Calcd for C12H15NO4Na [(M+Na)+] 260.0893. Found 260.0891.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,95652-80-5, its application will become more common.

Reference:
Article; Inai, Makoto; Ouchi, Hitoshi; Asahina, Aya; Asakawa, Tomohiro; Hamashima, Yoshitaka; Kan, Toshiyuki; Chemical and Pharmaceutical Bulletin; vol. 64; 7; (2016); p. 723 – 732;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 112110-07-3, 5-(Trifluoromethyl)pyridin-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, 112110-07-3, blongs to pyridine-derivatives compound. Formula: C6H5F3N2

A mixture of Pd2(dba)3 (11 mg, 0.012 mmol) and BrettPhos (13 mg, 0.025 mmol) in l,4-dioxane (1 mL) was stirred at 50 C for 10 min. l-(3-chloro-5-methyl-5H-chromeno[4,3- c]pyridin-8-yl)pyrrolidin-2-one (80 mg, 0.25 mmol), 5-(trifluoromethyl)pyridin-3-amine (49 mg, 0.30 mmol) in dioxane (5 mL) and CS2CO3 (248 mg, 0.762 mmol) were added and the resulting mixture was stirred at 100 C for 16 h. A black brown mixture was formed. LCMS (Rt = 0.702 min; MS Calcd: 440.2; MS Found: 440.9 [M+H]+). The reaction mixture was diluted with DCM (10 mL), filtered and concentrated. The residue was purified by prep-HPLC (0.05% NH32O as an additive) and lyophilized to give l-(5-methyl-3-((5- (trifluoromethyl)pyridin-3-yl)amino)-5H-chromeno[4,3-c]pyridin-8-yl)pynOlidin-2-one (25.0 mg, yield: 22%) as a white solid. (1164) NMR (400 MHz, DMSO-r/e) d 1.53 (3H, d, J= 6.8 Hz), 2.00-2.09 (2H, m), 2.52 (2H, overlap with DMSO), 3.83 (2H, t , J= 7.6 Hz), 5.29 (1H, q, J= 6.8 Hz), 6.77 (1H, s), 7.30 (1H, dd, J = 8.4, 2.0 Hz), 7.39 (1H, d, J= 2.0 Hz), 7.91 (1H, d, J= 8.4 Hz), 8.42 (1H, s), 8.74 (1H, s), 9.79 (1H, t, J = 2.0 Hz), 8.94 (1H, d, J= 2.4 Hz), 9.85 (1H, brs).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,112110-07-3, its application will become more common.

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; FORSBLOM, Rickard; GINMAN, Tobias; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (391 pag.)WO2019/126730; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88912-24-7, 5,6-Dichloropicolinic 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, 88912-24-7, blongs to pyridine-derivatives compound. Recommanded Product: 88912-24-7

Sodium hydride (CAN 7646-69-7, 60% w/w, 1.05 g, 26 mmol) was added tocyclopropylmethanol (CAN 2516-33-8, 7.5 g) at 0C and the mixture was stirred for 1 h. 5,6-Dichloro-pyridine-2-carboxylic acid (1 g, 5 mmol) was added and the mixture was heated to 95C for 3 h. The solvent was removed under reduced pressure. The residue was diluted with water (10 mL) and adjusted to pH = 3.0 by hydrochloric acid (3 N). The solution was extracted with ethyl acetate (3 x 15 mL). The combined organic layers were washed with water (3 x 30 mL) and brine (2 x 40 mL) and evaporated to dryness to give the crude product (0.35 g, 25%>), which was used in the next step without further purification, MS (EI): m/e = 228.1 [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,88912-24-7, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BISSANTZ, Caterina; GRETHER, Uwe; HEBEISEN, Paul; KIMBARA, Atsushi; LIU, Qingping; NETTEKOVEN, Matthias; PRUNOTTO, Marco; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; ULLMER, Christoph; WANG, Zhiwei; YANG, Wulun; WO2012/168350; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5444-01-9, 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.5444-01-9, name is 4-Methylnicotinonitrile, molecular formula is C7H6N2, molecular weight is 118.1359, as common compound, the synthetic route is as follows.

1M LiHMDS (45mL, 44.794mmol) was added to a solution of 4- methylnicotinonitrile (2.52g, 21.33mmol) in THF (15mL) at -78C and the resulting reaction mass was stirred at -78C for 1 hour. This was followed by the addition of dimethyl carbonate (1.98mL, 23.464mmol) and stirred the resulting reaction mass at – 78C for 1 hour and further at 0C for 2 hours. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mass was quenched with saturated NH4C1 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, CDC13): delta 8.9 (s, 1H), 8.79 (d, 1H), 7.4 (d, 1H), 3.9 (s, 2H), 3.79 (s, 3H)

The chemical industry reduces the impact on the environment during synthesis 5444-01-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BOCK, Mark G.; GAUL, Christoph; GUMMADI, Venkateshwar Rao; MOEBITZ, Henrik; SENGUPTA, Saumitra; WO2012/35078; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 274-76-0, 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.274-76-0, name is Imidazo[1,2-a]pyridine, molecular formula is C7H6N2, molecular weight is 118.1359, as common compound, the synthetic route is as follows.

a) Imidazo [1, 2-a] pyridine-3-carbaldehyde; Imidazo [1, 2-a] pyridine (0.500 g, 4.23 mmol) was dissolved in 1 mL of DMF and phosphorus oxychloride (0.71 g, 4.6 mmol) was added dropwise and the mixture was stirred and checked on LC-MS. After lh the mixture was poured into water and made alkaline with 1M NaOH. The mixture was extracted three times with EtOAc and the combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated. The crude product was flash chromatographed on silica gel with DCM: MeOH 99: 1-96: 4. Yield: 83 mg (13%). ‘H NMR (300 MHz, CDCl3) 6 9.95 (s, 1H), 9.50 (m, 1H), 8.32 (s, 1H), 7.80 (m, 1H), 7.56 (m, 1H), 7.13 (m, 1H).

The chemical industry reduces the impact on the environment during synthesis 274-76-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2005/66132; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 76006-11-6, 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.76006-11-6, name is 7-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

Pyrazolopyridine 6 (0.44 g, 2.9 mmol) was dissolvedin dry methanol (50 mL) and N-iodosuccinimide (1.0 g,4.4 mmol) was added in portions. The mixture was stirred atroom temperature for 2h. Then, the solvent was removedunder reduced pressure and the residue was extracted withethyl acetate. The combined organic extracts were washedwith aqueous sodium thiosulfate (10% w/v) solution, thendried over sodium sulfate, filtered and concentrated. Thecrude product was purified by column chromatography (silicagel) using a mixture of cyclohexane/ethyl acetate (6/4,v/v) as the eluent to provide pure 7 as a yellow solid, in 99% yield. mp 252-3 C (EtOAc). 1H NMR (600 MHz, DMSO-d6) 7.50 (d, 1H, H-4, J = 5.5Hz), 8.08 (d, 1H, H-5, J =5.5Hz). HR-MS (ESI) m/z: calcd for C6H4ClIN3, [M1+H]+ =279.9133, found 279.9128. Anal. Calcd for C6H3ClIN3: C,25.79; H, 1.08; N, 15.04. Found: C, 25.91; H, 1.13; N, 14.88.

Statistics shows that 76006-11-6 is playing an increasingly important role. we look forward to future research findings about 7-Chloro-1H-pyrazolo[3,4-c]pyridine.

Reference:
Article; Gavriil, Efthymios-Spyridon; Lougiakis, Nikolaos; Pouli, Nicole; Marakos, Panagiotis; Skaltsounis, Alexios-Leandros; Nam, Sangkil; Jove, Richard; Horne, David; Gioti, Katerina; Pratsinis, Harris; Kletsas, Dimitris; Tenta, Roxane; Medicinal Chemistry; vol. 13; 4; (2017); p. 365 – 374;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 67058-77-9, Adding some certain compound to certain chemical reactions, such as: 67058-77-9, name is 3-Nitro-1H-pyrrolo[2,3-c]pyridine,molecular formula is C7H5N3O2, 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 67058-77-9.

To a solution of 3-nitro-1H-pyrrolo[2,3-c]pyridine (200 mg, 1.23 mmol) in MeOH (20 mL) was added 10% Pd/C (130 mg, 0.12 mmol). After stirred at balloon hydrogen atmosphere for 2 hrs, the mixture was filtered. The filtrate was evaporated in vacuum to give 1H- pyrrolo[2,3-c]pyridin-3-amineas a crude product which was used for next step without further purification.

According to the analysis of related databases, 67058-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
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.98273-79-1, name is Methyl 3-chloroisonicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Quality Control of Methyl 3-chloroisonicotinate

A solution of 1-(bromomethyl)-4-(methylsulfanyl)benzene (prepared according to D. D. M. Wayner, D. R. Arnold, Can J. Chem., 1984, 62, 1164) (2.54 g, 11.7 mmol) in THF (10 mL) was added dropwise to a slurry of Riecke Zinc in THF (22.8 mL of a commercial suspension [5g Zn/100 mL], 17.5 mmol) under nitrogen. During this time the temperature rose steadily to 35C. After allowing the black slurry to cool to room temperature over 30 min bis(triphenylphosphine)nickel (II) chloride (762 mg, 1.17 mmol) was added followed by a solution of methyl 3-chloroisonicotinate (prepared according to J. Epsztajn, M. W. Plotka, A. Grabowska, Synth. Commun., 1997, 27, 1075) (1.0 g, 5.83 mmol) in THF (10 mL), dropwise, taking care to keep the temperature below 30C. After the addition was complete the reaction was allowed to cool to room temperature over 1 h before being quenched by the addition of sat. NH4Cl (aq) (20 mL) while cooling with an ice bath. The mixture was filtered through Celite ), washing well with EtOAc (3 x 20 mL), the organic layer was separated, dried (MgS04) and evaporated to give a brown oil. The residue was purified by column chromatography [SiO2; EtOAc:pentane, 1:3 increasing polarity to EtOAc:pentane, 1:1 and then to (EtOAc:MeOH:NH40H, 95:5:0.5):pentane, 1:1] to give the title compound as an orange oil; & delta H (CDCl3, 400 MHz) 2.43 (3H, s), 3.82 (3H, s), 4.30 (2H, s), 7.05 (2H, d), 7.18 (2H, d), 7.67 (1H, br), 8.59 (2H, br); MS m/z (TS+) 274 (MH+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Limited; Pfizer Inc.; WO2004/16593; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem