Day: November 9, 2020

19524-06-2, 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. 19524-06-2, name is 4-Bromopyridine hydrochloride, molecular formula is C5H5BrClN, 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.

[Referential Example 237] 4-(Pyridin-4-yl)benzoic acid hydrochloride: 4-Bromopyridine hydrochloride (11.7 g) and 4-carboxyphenylboric acid (10.0 g) were dissolved in a mixed solvent of toluene (250 ml) and water (250 ml), tetrakis(triphenylphosphine)palladium(0) (5.0 g) and anhydrous sodium carbonate (25.4 g) were successively added, and the mixture was heated under reflux at 120¡ãC for 19 hours.. After the reaction mixture was cooled to room temperature, ethyl acetate was added to the reaction mixture to extract it with water.. concentrated hydrochloric acid was added to the water layer to acidify it.. The water layer was washed with ethyl acetate and then concentrated, and solids deposited were collected to obtain the title compound (8.37 g).1H-NMR (DMSO-d6) delta: 8.11(2H,d,J=8.8Hz), 8.14(2H,DJ=8.8Hz), 8.35(2H,d,J=6.6Hz), 8.97(2H,d,J=6.6Hz). MS (FAB) m/z: 200(M+H)+.

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. 19524-06-2, 4-Bromopyridine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1405852; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

16063-70-0, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 16063-70-0, name is 2,3,5-Trichloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of /e/ – butyl N-(2-amino-5-fluoro-phenyl)-N-methyl-carbamate (142.0 g, 0.591 mol) and 2,3,5-trichloropyridine (108.0 g, 0.591 mol) in dioxane (2.0 L) was added CS2CO3 (385.0 g, 1.18 mol). The mixture was degassed with nitrogen for 2 min before Pd(OAc)2 (13.3 g, 0.059 mol) and BINAP (73.5 g, 0.118 mol) were addedunder nitrogen. After the charging was completed, the suspension was heated to 110 C and stirred for 3 h. After TLC (petrolieum ether:EtOAc = 20 : 1) showed the reaction was completed, the reaction mixture was cooled back to r.t., diluted with EtOAc (3.0 L) and filtered. The filtrate was concentrated in vacuo to give a crude product, which was purified by silica gel flash chromatography (petroleum ether:EtOAc = 500 : 1 ~ 20 : 1) to give ieri-butyl N-[2-[(3,5-dichloro-2-pyridyl)amino]-5-fluoro- phenyl]-N-methyl-carbamate (190.0 g, 83.2% yield) as a white solid. MS (ESI): 385.9

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 16063-70-0, 2,3,5-Trichloropyridine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DING, Xiao; LIU, Yongqiang; SHEN, Hong; SHI, Houguang; TAN, Xuefei; ZHOU, Chengang; ZHOU, Mingwei; (163 pag.)WO2020/64661; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding some certain compound to certain chemical reactions, such as: 97483-77-7, name is 5-Bromopicolinonitrile, 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 97483-77-7. 97483-77-7

5-(piperidin-1-yl)picolinonitrile A solution of 500 mg (2.73 mmol) 5-bromopicolinonitrile, 63 mg (0.07 mmol) Pd2 dba3 and 130 mg (0.27 mmol) 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl in 20 ml DME was stirred and degassed with N2 for 10 min. 1.45 g (6.83 mmol) K3PO4 and 297 mul (3.0 mmol) piperidine were added. The mixture was heated at 80 C. under N2 over night. The mixture was cooled to r.t. and filtered through a plug of SiO2 with CH2Cl2/MeOH 9:1. The filtrate was concentrated and purified by flash chromatography (SiO2, Pet. ether/EtOAc 4:1?1:1) to afford 323 mg (63%, yellow oil). 1H NMR (CDCl3) delta 8.28 (d, 1H), 7.47 (d, 1H), 7.05 (m, 1H), 3.37 (m, 4H), 1.69 (m, 6H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 97483-77-7.

Reference:
Patent; RESPIRATORIUS AB; US2012/40942; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

109-04-6, 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. 109-04-6, name is 2-Bromopyridine. A new synthetic method of this compound is introduced below.

To a -40 C solution of 2.5 M n-BuLi (18 mL) in THF (300 mL) is added 2- bromopyridine (5.0 g, 32 mmol) over 15 min. The reaction is stirred for 1 h at -40 C, and then treated with 2-Amino-5-bromo-benzoic acid (6.9 g, 32 mmol) in THF (300 mL). The reaction is warmed to 0 C and stirred for 2 h then quenched with TMSC1 (3.4 g, 32 mmol). The reaction is stirred at room temperature for 30 min then cooled to 0 C and quenched with 3M HCl (20 mL). The aqueous layer is separated and the organic layer is extracted with 3M HCl. The organic layer is basified with solid NaOH, the resulting mixture is extracted with EtOAc, and the organic layer is dried over Na2S04, filtered and concentrated. The residue is purified by column chromatography on silica gel to give the desired product as a yellow solid. Yield: 5.50 g (62.7%) HPLC-MS: M+H=277/279; tRet =3.16 min; AM6

At the same time, in my other blogs, there are other synthetic methods of this type of compound,109-04-6, 2-Bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; SMETHURST, Christian; ENGELHARDT, Harald; GIANNI, Davide; REISER, Ulrich; WO2014/154762; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

620-08-6, 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. 620-08-6, name is 4-Methoxypyridine, molecular formula is C6H7NO, 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 solution of t-butyllithium in THF (1.7 M, 9.7 mL, 16.5 mmol, 2.1 eq) in THF (40 mL) maintained at -78 C was added 2-bromomesitylene (1.6 g, 8.0 mmol, 1.3 eq) dropwise. The resulting solution was stirred for 1 h at -78 C, then 4-methoxypyridine (681 mg, 0.63 mL, 6.2 mmol) was added and the mixture was warmed to -20 C in an ice-salt bath. After stirring for 3 h at -20 C, the mixture was cooled back to -78 C and DMF (1.17 g, 16.0 mmol, 2.0 eq) was added. The reaction mixture was stirred for 1 h, quenched with brine at -78 C and extracted with diethyl ether (3 ¡Á 100 mL). The combined organic extracts were dried over K2CO3, filtered and evaporated to yield a crude oil that was purified by silica gel chromatography using 1:1 EtOAc:hexanes to yield 405 mg (47.6%) of product as a pale yellow oil: Rf 0.25 (1:1 hexane:EtOAc); 1H NMR (300 MHz, CDCl3) delta 10.43 (s, 1H), 8.87 (s, 1H), 8.62 (d, 1H), 6.92 (d, 1H), 4.1 (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. 620-08-6, 4-Methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Williams, John D.; Khan, Atiyya R.; Cardinale, Steven C.; Butler, Michelle M.; Bowlin, Terry L.; Peet, Norton P.; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 419 – 434;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 271-63-6 as follows., 271-63-6

A solution of 1H-pyrrolo[2,3-b]pyridine (1.0 g, 1 equiv.) in DMF (30 mL) at 0 C wastreated portionwise with NB S (1.51 g, 1 equiv.) under argon, and the resulting solution wasstirred at 0 C for 20 mm. The reaction mixture was allowed to warm to RT and stirring was continued for 10 mm. Then, the reaction mixture was transferred to a separatory funnel containing distilled water, and extracted with EtOAc (2×150 mL). Combined organic extracts were dried over Na2SO4, were filtered, and the solvent was removed invacuo. The crude product was recrystallized from DCM to afford the expected product (1.55 g). LCMS: IVIW (calc?d): 197.0; MS (ES, m/z): 197.3, 199.3 [M+H].

The chemical industry reduces the impact on the environment during synthesis 271-63-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; E-THERAPEUTICS PLC; KOLUND?IC, Filip; MILEK, Mateja; POLJAK, Tanja; RO?CIC, Maja; STUBBERFIELD, Colin; VADLAMUDI, Srinivasamurthy; (139 pag.)WO2019/43373; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The common heterocyclic compound, 72830-09-2, name is 2-Chloromethyl-3,4-dimethoxypyridinium chloride, molecular formula is C8H11Cl2NO2, 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. 72830-09-2

General procedure: 2-Chloromethyl pyridine hydrochloride (0.8 g, 5.0 mmol), 2-chloromethyl-4-methoxy-3-methylpyridine hydrochloride (1.0 g, 5.0 mmol), 2-chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride (1.1 g, 5.0 mmol), 2-chloromethyl-3,4-dimethoxypyridine hydrochloride (1.12 g, 5.0 mmol), K2CO3 (1.1 g, 8.0 mmol) and KI (1.32 g, 8 mmol) were added to a magnetically stirred solution of 9 (1.24 g, 5.0 mmol) in a mixture of acetone (30 ml) and ethanol (30 ml). The reaction mixture was stirred constantly at 60 C for about 8 h. When the reaction was finished, as monitored by TLC, water (100 ml) was added. Then the reaction mixture was extracted with DCM (30 ml ¡Á 4). The organic phase was combined and concentrated under reduced pressure gave crude compounds 11a-d.

The synthetic route of 72830-09-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; El-Nezhawy, Ahmed O.H.; Biuomy, Ayman R.; Hassan, Fatma S.; Ismaiel, Ayman K.; Omar, Hany A.; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1661 – 1670;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1121-60-4, Adding a certain compound to certain chemical reactions, such as: 1121-60-4, Picolinaldehyde, 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, 1121-60-4, blongs to pyridine-derivatives compound.

General procedure: In a typical experiment,a mixture of aromatic aldehyde 2 (1mmol) and o-phenylenediamine (1) (1 mmol) was taken in a test tube.The reaction mixture was stirred on magnetic stirrer in concentrated solar radiation (CSR) for 20-30 minutes and monitored by TLC. On completion of the reaction, the reaction mixture was cooled to room temperature.The 2-aryl-1H-benzimidazoles 3 were isolated by using column chromatography over Silica gel using hexane-EtOAc as eluent as and when required.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1121-60-4, its application will become more common.

Reference:
Article; Harsh, Simran; Yusuf, Mohamad; Sharma, Rohit; Kumar, Yogesh; Kumar, Rupesh; Arkivoc; vol. 2018; 7; (2018); p. 119 – 130;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

72830-09-2, 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. 72830-09-2, name is 2-Chloromethyl-3,4-dimethoxypyridinium chloride, molecular formula is C8H11Cl2NO2, 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 I 2 Preparation of 5-chloro-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole 2-chloromethyl-3,4-dimethoxypyridine hydrochloride (896 mg, 0.004 mol) was dissolved in 25 ml MeOH and treated with NaOH (390 mg, 0.008 mol) dissolved in 1.5 ml H2 O. 5-chloro-2-mercapto-1H-benzimidazole (812 mg, 0.0044 mol) was added and the resulting mixture allowed to react for 2h at room temperature. The solvent was evaporated and the residue partitioned between 50 ml 2.5 % NaOH and 75 ml CH2 Cl2. The aqueous layer was separated and extracted twice with 25 ml CH2 Cl2. The organic layers were combined, washed with 25 ml H2 O, dried over MgSO4 and the solvent was evaporated. The crude product was triturated with approximately 5 ml of EtOAc saturated with NH3. The solid was collected and the mother liquor reprocessed furnishing 650 mg (48%) of the title compound as an off white powder.

The chemical industry reduces the impact on the environment during synthesis 72830-09-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aktiebolaget Hassle; US5019584; (1991); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 628-13-7, Pyridinehydrochloride, 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, 628-13-7, blongs to pyridine-derivatives compound. 628-13-7

This material was dissolved in methanol and 5 mL of saturated HCl in ethyl acetate was added and concentrated to give the hydrochloride salt. To 2 g of the above pyridine hydrochloride salt in 15 mL of methanol was added 0.225 g of platinum oxide and hydrogenated at 50 psi on the Parr shaker for 2 h. The catalyst was filtered off through a pad of celite and washed with methanol. The filtrate was concentrated to give 2.17 of the piperidine hydrochloride as a foam. STR123 The title compound was prepared from the compound made in Step A and Intermediate 3 as described previously. 1 H NMR (400 MHz, CD3 OD mixture of rotamers): 8.10 (t, 1H), 7.78 (dd, 1H), 7.50-7.00 (m, 8H), 4.90 (m, 1H), 4.55 (d, 1H), 3.94 and 3.90 (2 doublets, 1H), 3.85 (s, 3H), 3.80-3.60 (m, 1H), 3.05 (dt, 1H), 2.70-2.50 (m, 4H), 1.90-1.50 (m, 6H), 1.55 (s, 3H), 1.50 9s, 3H), 1.40 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,628-13-7, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US5492920; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem