Day: September 1, 2021

Electric Literature of 153034-94-7 ,Some common heterocyclic compound, 153034-94-7, molecular formula is C6H5FIN, 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.

Step 1: N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine A solution of 2-fluoro-4-iodo-5-methylpyridine (85 g, 340 mmol) in 1-(2,4-dimethoxyphenyl)methanamine (270 mL, 1.68 mol) was allowed to stir at 110 C. overnight. The reaction mixture was allowed to cool to rt and diluted with EtOAc. A precipitate formed and was filtered and then washed with EtOAc. The solid was purified further by column chromatography to give N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine (138 g, 50%).

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. 153034-94-7, 2-Fluoro-4-iodo-5-picoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Bharathan, Indu T.; Blackburn, Chris; Ciavarri, Jeffrey P.; Chouitar, Jouhara; Cullis, Courtney A.; D’Amore, Natalie; Fleming, Paul E.; Gigstad, Kenneth M.; Gipson, Krista E.; Girard, Mario; Hu, Yongbo; Lee, Janice; Li, Gang; Rezaei, Mansoureh; Sintchak, Michael D.; Soucy, Francois; Stroud, Stephen G.; Vos, Tricia J.; Wong, Tzu-Tshin; Xu, He; Xu, Tianlin; Ye, Yingchun; US2015/225422; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71255-09-9, 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. 71255-09-9, name is 2-Methoxynicotinaldehyde, molecular formula is C7H7NO2, 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.

A round bottom flask was charged with 0.44g (3.23mM) of 2-methoxy-3-pyridine carboxaldehyde (24), 1.24g (16.15mM) of ammonium acetate, and 0.61g (19.69mM) of sodium cyanoborohydride. The flask was then flushed with argon, and then 5OmL of dry MeOH was added by syringe. The reaction was stirred for 2 days, at which point the MeOH was evaporated off. 25mL of water was added, and the mixture was brought to pH 2 with cone. HCl. This was extracted twice with EtOAc to remove the alcohol side product. The mixture was brought to pH 10 using sodium hydroxide pellets, saturated with NaCl, and extracted twice with DCM and once with EtOAc. The combined organics were dried and evaporated to give 0.31g (69%) of 3-aminomethyl-2-methoxypy?dine (25).

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 71255-09-9, 2-Methoxynicotinaldehyde.

Reference:
Patent; PHARMACOPEIA , INC.; WO2008/60301; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 183208-35-7, 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 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 1; Compound 1-1; 5-?-methyl-lH-pyrazol-4-yl)-3-(6-piperazin-l-ylpyrazin-2-v?-lH-pyrrolor2,3-b1pyridine; Step 1 : 5-bromo-l-(phenylsulfonylMH-pyrrolo[2,3-fr]rhoyridine; To a stirred solution of 5-bromo-lH-pyrrolo[2,3-Z>]pyridine (20.0 g, 102 mmol) in DMF (400 ml) at 0 0C was added NaH (60% mineral oil dispersion; 4.87 g, 122 mmol) slowly (CAUTION: GAS EVOLUTION). The reaction mixture was stirred at 0 C for 2 h. Benzenesulfonyl chloride (17.0 ml, 132 mmol) was added dropwise, and the reaction mixture was allowed to warm to ambient. After 1 hour the reaction mixture was cooled in an ice bath, and 100 mL of water was added slowly (CAUTION: GAS EVOLUTION, EXOTHERM). The reaction mixture was partitioned between ethyl acetate (500 mL) and brine (600 mL). The organic layer was washed with additional brine (500 mL), followed by saturated aqueous ammonium chloride (250 mL). The first and 3rd aqueous layers were combined and back- extracted with ethyl acetate (500 mL). The combined organics were dried over sodium sulfate, filtered and concentrated to a thick slurry. EtOAc (100 mL) was added, followed by hexanes (100 mL). The mixture was filtered, and the filter cake was rinsed with 1 :1 EtOAc/Hexanes (50 mL) to afford 5-bromo-l-(phenylsulfonyl)-lH-pyrrolo[2,3-£]pyridine as a grey solid. The filtrate can be concentrated and purified by silica gel chromatography (EtOAc/etaexanes gradient) to afford additional product. LRMS (ESI) calculated for C13H9BrN2O2S [M+H]+, 337.0; found 336.9.

According to the analysis of related databases, 183208-35-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2009/54941; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 905306-69-6, 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 905306-69-6, name is (5-Methoxypyridin-2-yl)methanamine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 1-(5-methoxypyridin-2-yl)methanamine (138 mg, 1 mmol) and 2-chloro-3-methyl-7-(propan-2-yl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one (90 mg, 0.4 mmol) in DMF (1.5 mL) was added DIEA (104 mg, 0.8 mmol). The reaction mixture was stirred at 50C for 10 h and purified by preparative HPLC (MeCN and H2O with 0.01% NH3.H2O as mobile phase) to give the titled compound (40 mg, yield 30 %).LC-MS (m/z) = 329 [M + H]+.1H-NMR (400 MHz, DMSO-d6): delta 1.40 (d, J = 7.2 Hz, 6H), 3.46-3.52 (m, 1H), 3.53 (s, 3H), 3.89 (s, 3H), 4.55 (d, J = 4.0 Hz, 2H), 6.07 (s, 1H), 7.27-7.31 (m, 2H), 7.75 (s, 1H), 8.26 (d, J = 2.4 Hz, 1H).

According to the analysis of related databases, 905306-69-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO DAINIPPON PHARMA CO., LTD.; FUJII, Yuki; FUJIWARA, Hiroaki; KAWASUMI, Muneo; IWAMA, Seiji; IKEDA, Tomoko; KIYOSHIGE, Saori; (219 pag.)WO2016/147659; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 98555-51-2, 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. 98555-51-2, name is 5-Bromopyridine-2,3-dicarboxylic acid. A new synthetic method of this compound is introduced below.

Example 12 2-Bromo-7-(4-fluoro-benzyl)-5,9-dihydroxy-pyrrolo[3,4-g]quinoline-6,8-dione; 1008 Following the literature procedure of M.-D. Le Bas et al. (Synthesis 2001, 16, p. 2495), 100 ml CCl4 was mixed with 250 ml of an aqueous NaOCl solution. To this mixture was added 40 mg of RuO2, followed by 3 g 3-bromoquinoline dissolved in 50 ml CCl4. Additional 30 ml portions of bleach were added at 2, 4, and 6 h. After 24 h, the aqueous layer was collected and acidified to pH 1 with 3N HCl. The aqueous layer was then extracted with ethyl acetate, dried over Na2SO4 and volatiles removed by evaporation to give the 1.7 g product as a yellow resin, (48% yield). 1H NMR and MS data matched that reported in the literature. The resulting anhydride, 1 g, was then carried through the previously reported multistep sequence to afford the corresponding cyano-ester. Dieckmann condensation between 80 mg (0.3 mmol) of the ester and 80 mg (3.6 mmol) of the imide utilizing 900 uL LiHMDS in 2 ml dry THF gave the crude product. After the typical work-up, approximately 60 mg (30%) of unpurified product was obtained as a yellow solid which was further refined by trituration with diethyl ether to provide 2 mg highly pure product 1008. 1H NMR (300 MHz, d6-DMSO) delta 9.20 (d, 1H), 9.05 (d, 1H) and 4.85 (s, 2H) ppm, MS=416.1 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98555-51-2, 5-Bromopyridine-2,3-dicarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Cai, Zhenhong R.; Jabri, Salman Y.; Jin, Haolun; Lansdown, Rachael A.; Metobo, Samuel E.; Mish, Michael R.; Pastor, Richard M.; US2008/58315; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 80194-68-9, 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 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

The third step: adding 0.25 g of 3-chloro-5-(trifluoromethyl)pyridinecarboxylic acid, 0.18 g of 2,4-dimethylbenzohydrazide, and 3 ml of phosphorus oxychloride to a three-necked flask, and heating and stirring for 10 hours. After pouring the liquid into a beaker containing ice water, adding Na2CO3 to adjust the pH = 9-10, suction filtration, drying, column chromatography to obtain the target compound.

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 80194-68-9, 3-Chloro-5-(trifluoromethyl)picolinic acid.

Reference:
Patent; Guizhou University; Wu Jian; Xu Fangzhou; Wang Yanyan; Luo Dexia; Xue Wei; (37 pag.)CN108218848; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 63071-10-3, 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 63071-10-3, name is (4-Chloropyridin-2-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

4-Chloro- 2-pyridinemethanol (400 mg, 0.0028 mol) was dissolved in chloroform (24 ml). Thionyl chloride (0.40 ml, 0.0056 mol) and DMF (2 drops) were added. The mixture was stirred 4 hours at 8O0C. The solvent was evaporated. The residue was taken back in MeOH (18 ml) and ethanolamine (1.38 ml, 0.014 mol) was added. The mixture was stirred 4 hours at 800C. The solvent was evaporated. The residue was poured out onto water and extracted with EtOAc. The organic layer was separated, washed with a saturated solution of sodium hydrogen carbonate, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (40-63mum) (eluent: DCM/MeOH 85/15). The pure fractions were collected and the solvent was evaporated, yielding 310 mg (60%) of intermediate 64 as an orange 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 63071-10-3, (4-Chloropyridin-2-yl)methanol.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/32631; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1033201-61-4, 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 1033201-61-4 as follows.

A slurry of 6-amino-3-bromopicolinic acid (25 g) in 400 mL 1:1 dichloromethane/chloroform was added to nitrosonium tetrafluoroborate (18.2 g) in dichloromethane (100 mL) at 5 C. over 1 hour. The resulting mixture was stirred for another 30 minutes, warmed to 35 C., and stirred overnight. The reaction mixture was cooled to room temperature and adjusted to pH 4 with a NaH2PO4 solution. The resulting solution was extracted three times with dichloromethane, and the combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to provide the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1033201-61-4, its application will become more common.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 148493-37-2, 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. 148493-37-2, name is 2,6-Dichloro-3-iodopyridine, molecular formula is C5H2Cl2IN, 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 1 necked round bottom flask, with stirrer, and air condenser, under nitrogen, is added 2,6-dichloro-3-iodo-pyridine (1.0 g, 3.8 mmol), 2- [(E)-2-ethoxyvinyl]-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (0.9 g, 4.8 mmol), CS2CO3 (3.75 g, 11.5 mmol), l,4-dioxane (19.2 mL), and water (4.26 mL). This reaction mixture is purged 3 times alternating between vacuum and nitrogen, and [l,T bis(diphenylphosphino) ferrocene]dichloropalladium(II) (0.2 g) is added. The resulting mixture is stirred for 3 hr at 90 C, the reaction is poured onto saturated aqueous NH4Cl, and the aqueous mixture is extracted three times with EtOAc. The combined organic extracts are dried over MgS04, filtered, and the filtrate is concentrated under reduced pressure. The resulting residue is purified by flash chromatography over silica gel, eluting with a gradient of 0-100% EtOAc in cyclohexane, to afford the title compound (748 mg, 89% yield), after solvent evaporation of the desired chromatographic fractions. NMR (300 MHz, CDCh): d 1.37 (m, 3H), 3.97 (m, 2H), 5.97 (m, 1H), 6.99 (m, 1H), 7.16 (m, lH),7.60 (m, 1H).

According to the analysis of related databases, 148493-37-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; DREYFUS, Nicolas Jacques Francois; FALLER, Andrew; (44 pag.)WO2019/245907; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 162102-79-6, Dimethyl 4-bromopyridine-2,6-dicarboxylate, 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, Computed Properties of C9H8BrNO4, blongs to pyridine-derivatives compound. Computed Properties of C9H8BrNO4

In a sealed tube, a mixture of 1 (2.74 g, 10 mmol)and (S)-phenylalaninol (3.78 g, 25 mmol) in methanol (10 mL) was stirred at 115 C for 12 h. After cooling to ambient temperature, the crude product was poured into crushed ice (100 g), stirred for15 min, filtered, washed with water (20 mL 3) and the residues was dried under vacuum. The white product was used for the next step without further purification (4.50 g, 88%). 1H NMR (400 MHz,CDCl3): d 8.43 (s, 2 H), 7.94 (d, J 8 Hz, 2 H), 7.32e7.21 (m, 10 H),4.40e4.32 (m, 2 H), 3.83e3.74 (m, 4 H), 3.06e2.96 (m, 4 H), 2.59 (br,2 H). 13C NMR (150 MHz, CDCl3): d 162.6, 149.7, 137.5, 136.4, 129.4,128.8, 128.5, 126.9, 63.6, 53.1, 37.0. HRMS (MALDITOF) calcd forC25H27BrN3O4 [M H] 512.1179, found 512.1186.

The synthetic route of 162102-79-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Ya-Qi; Pan, Yao; Gao, Wan-Qing; Wu, Yuan; Liu, Chun-Hua; Zhu, Yuan-Yuan; Tetrahedron; vol. 75; 28; (2019); p. 3809 – 3814;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem