Tag: M.W:100-200

Reference of 55876-82-9, 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. 55876-82-9, name is Ethyl 5-methylpicolinate. A new synthetic method of this compound is introduced below.

To a solution of methyl 5-methylpyridine-2-carboxylate [Example 2, Step 1] (3 g, 18.3 mmol, 1.00 equiv) in ethanol (20 mL) and tetrahydrofuran (20 mL) was added CaCl2 (8.125 g, 549 mmol 4.00 equiv) and NaBH4 (1.38 g, 36.6 mmol, 2.00 equiv). The resulting solution was stirred overnight at 50 C. The solids were filtered out. The filtrate was concentrated under vacuum. The resulting solution was diluted with ethyl acetate (50 mL). The solids were filtered out. The filtrate was concentrated under vacuum to afford 2.6 g (88.9%) of (5-methylpyridin-2-yl)methanol as light yellow oil. LC-MS: m/z=124[M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55876-82-9, Ethyl 5-methylpicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Auspex Pharmaceuticals, Inc.; ZHANG, Chengzhi; (94 pag.)US2018/79742; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 134363-45-4, 2-(Pyridin-3-yl)benzoic 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, HPLC of Formula: C12H9NO2, blongs to pyridine-derivatives compound. HPLC of Formula: C12H9NO2

To a solution of 4-(4-Amino-2-fluoro-phenyl)-piperazine-1 -carboxylic acid te/t-butyl ester (1.00 g, 3.4 mmol) and 2-pyhd-3-yl benzoic acid (0.70 g, 3.7 mmol) in DMF (10 ml_) was added HATU (1.42 g, 3.7 mmol) and diisopropylamine (0.65 ml_, 3.7 mmol). After stirring at room tempertaure for 18 h, the reaction mixture was diluted with EtOAc (100 ml_) and washed with H2O (4×50 ml_). The organic extracts were combined, dried (Na2SO4), and the solvent was evaporated under reduced pressure. Chromatography of the resulting residue (SiO2: EtOAc:Hex) yielded 4-[2-fluoro-4-(2-pyridin-3-yl- benzoylamino)-phenyl]-piperazine-1 -carboxylic acid te/t-butyl ester which was further dissolved in MeOH (20 ml_) and 4N HCI in dioxanes. After stirring for 5 h, the reaction mixture was concentrated down, neutralized with 1 N NaOH, and extracted with EtOAc (3x75ml_). The organic extracts were combined, dried (Na2SO4), and the solvent was evaporated under reduced pressure to yield the title compound.MS: mass calcd. for C22H21FN4O, 376.17; m/z found, 378.4 [M+H]+

The synthetic route of 134363-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2009/6185; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 61494-55-1, 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid. A new synthetic method of this compound is introduced below.

Acetyl chloride (0.651 mL, 9.18 mmol) was added to a suspension of (2- chloropyridin-3-yi)acetic acid (1117) (1.048 g, 6.108 mmol) in MeOH (30 mL). The mixture was heated at reflux for 20 hours. The voiatiles were removed in vacuo and the residue partitioned between DCM (100 mL) and sat. NaHC03 (100 mL). The layers were separated and the aqueous layer extracted with DCM (2×100 mL). The combined organic layers were washed with brine (100 mL), dried (Na2S04) and the solvent removed under reduced pressure to yield an oil which was purified by column chromatography on silica gel (0-40% EtOAc in petroleum benzine 40-60 C) to afford the title compound (1118) (0.863 g, 76%) as a pale yellow oil; 1H NMR (400 MHz, d6~ DMSO) delta 8.34 (dd, J = 4.8, 1.9 Hz, 1 H), 7.83 (dd, J = 7.5, 1.9 Hz, 1 H), 7.43 (dd, J = 7.5, 4.8 Hz, 1 H), 3.86 (s, 2H), 3.65 (s, 3H). LC S Method C: rt 5.04 min; m/z 186 [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,61494-55-1, its application will become more common.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; DEVLIN, Mark Graeme; STREET, Ian Philip; TONG, Warwick Bonner; WO2014/27199; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 898746-42-4, 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. 898746-42-4, name is 6-Fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5FN2, 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.

Preparation 17Synthesis of l-cyclopropyl-6-fluoro-lH-pyrrolo[2,3-b]pyridine.To a solution of 6-fluoro-lH-pyrrolo[2,3-b]pyridine (6.2 g, 45.55 mmol) in dryDCM (250 mL) is added cyclopropylboronic acid (7.82 g, 91.09 mmol), followed by cupric acetate (8.36 g, 45.55 mmol), sodium carbonate (9.65 g, 91.09 mmol) and 2,2′- bipyridine (7.1 1 g, 45.55 mmol). The resulting mixture is stirred and heated at 50C for 15h. The mixture is cooled to room temperature and further cupric acetate (4.18 g, 22.77 mmol) and sodium carbonate (2.41 g, 22.77 mmol) are added, followed bycyclopropylboronic acid (1.96 g, 22.77 mmol). The mixture is stirred and heated at 50C for a further 15h when further cupric acetate (1.5 g, 8.25 mmol) and cyclopropylboronic acid (1.49 g, 17.34 mmol) are added. The mixture is stirred at room temperature for 4 days and then poured onto sat. aq. NH4C1, diluted with water and extracted with DCM. The organic layers are combined, washed with brine, dried (magnesium sulphate) and concentrated in vacuo to give a green oil, which is purified by column chromatography on silica, eluting with DCM, to give the title compound (2.03 g, 11.52 mmol). MS (m/z): 177 (M+l). Unreacted 6-fluoro-lH-pyrrolo[2,3-b]pyridine is also recovered (3.012g, 22.1 mmol). MS (m/z): 137 (M+l).

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 898746-42-4, 6-Fluoro-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; ELI LILLY AND COMPANY; LAMAS-PETEIRA, Carlos; RICHARDS, Simon, James; SAPMAZ, Selma; WALTER, Magnus, Wilhelm; WO2012/74769; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89488-30-2, 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. 89488-30-2, name is 5-Bromo-3-methylpyridin-2(1H)-one, 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.

EXAMPLE 11B 5-bromo-2-chloro-3-methylpyridine The product from Example 11A (4.1 g, 221.8 mmol) in DMF (40 mL) was treated with phosphorus oxychloride (10 g, 65.4 mmol) dropwise at 0 C. After heating at 120 C. for 2 hours, the mixture was cooled and poured onto ice/water. The mixture was made basic with NH4OH, filtered, and the filtercake washed with ice water. The obtained solid was dissolved in dichloromethane (100 mL), washed with brine, and dried (MgSO4). The dried solution was filtered through a pad of silica using dichloromethane and the filtrate concentrated to provide the title compound as a white solid (3.48 g, 78% yield): 1H NMR (CDCl3, 300 MHz) delta 2.39 (s, 3H), 7.70 (m, 1H), 8.31, d, J=3 Hz, 1H).

According to the analysis of related databases, 89488-30-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schrimpf, Michael R.; Tietje, Karin R.; Toupence, Richard B.; Ji, Jianguo; Basha, Anwer; Bunnelle, William H.; Daanen, Jerome F.; Pace, Jennifer M.; Sippy, Kevin B.; US2002/19388; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 72600-67-0, name is 2-Chloro-3-fluoro-5-(trifluoromethyl)pyridine, molecular formula is C6H2ClF4N, 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. COA of Formula: C6H2ClF4N

(c) 47.7 g (0.82 mol) of potassium fluoride and 10.0 g (0.065 mol) of caesium fluoride are suspended in 300 ml of sulfolane and the suspension is heated to 140 C. 60 ml of sulfolane are distilled off by decreasing the pressure and subsequently 65.6 g (0.329 mol) of 2-chloro-3-fluoro-5-trifluoromethylpyridine and 1.3 g (0.004 mol) of 18-crown-6 are added. The reaction mixture is stirred for 48 hours at 140 C. and subsequently distilled by introducing steam. The oil is separated and the aqueous phase is extracted twice with a small amount of ether. The organic phases are purified, dried with a small amount of magnesium sulfate and filtered. Distillation affords 54.8 g (91% of theory) of 2,3-difluoro-5-trifluoromethylpyridine, b.p. 100-102 C. (980 mbar).

With the rapid development of chemical substances, we look forward to future research findings about 72600-67-0.

Reference:
Patent; Ciba-Geigy Corporation; US4831148; (1989); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 184416-84-0, 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.184416-84-0, name is 2,3-Dichloroisonicotinic acid, molecular formula is C6H3Cl2NO2, molecular weight is 192, as common compound, the synthetic route is as follows.

Thionyl chloride (92 mu, 1.25 mmol) is added to a mixture of 2,3-dichloro- pyridine-4-carboxylic acid (200 mg, 1.04 mmol), DCM (2 ml) and DMF (20 mu). The mixture is heated to 100C for 10 minutes in a microwave. The mixture is concentrated in vacuo. DCM (2.5 ml) and 1 ,2-dimethylhydrazine dihydrochloride (207 mg, 1.55 mmol) is added before DIPEA (1.35 ml, 7.77 mmol) in DCM (2.5 ml) is added dropwise at RT. Stirring is continued for 1 hour. The mixture is diluted with DCM and extracted with water. The combined organic layers are dried over Na2S04 and concentrated in vacuo. NMP (1 ml) and triethylamine (200 mu, 1.5 mmol) is added and the mixture heated to 190C for 25 minutes in a microwave. At RT water is added (500 mu) and the product purified by RP HPLC. Yield: 50 mg (24%). HPLC-MS: M+H=198; tR=0.44 min (METHOD l).

Statistics shows that 184416-84-0 is playing an increasingly important role. we look forward to future research findings about 2,3-Dichloroisonicotinic acid.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; WO2015/25018; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19230-59-2, 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 19230-59-2, name is 2-Methoxy-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

(lb) 2-Methoxy-3-methyl-5-nitropyridine [Formula 9]; Concentrated sulfuric acid (5 ml) and fuming nitric acid (5 ml) were added to 2-methoxy-3- methylpyridine (1.61 g, 13.1 mmol) under ice cooling, and stirred at 0C for 1 hour and further stirred at room temperature overnight. The reaction mixture was poured onto ice, neutralized with ammonia solution, extracted with ethyl acetate, dried over magnesium sulfate, the solvent was evaporated, thereby yielding the title compound (1.63 g, 9.71 mmol, and 74%). ¹H NMR(400MHz, DMSO-d6) 8 ppm; 2.25(3H, s), 4.04(3H, s), 8.37-8.40(lH, m), 8.92-8.95 (1H, m).

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 19230-59-2, 2-Methoxy-3-methylpyridine.

Reference:
Patent; EISAI CO., LTD.; WO2005/103049; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 59290-81-2, 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. 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid. A new synthetic method of this compound is introduced below.

A solution of 2-methyl-5-nitronicotinic acid 1 (50 mg, 0.27 mmol), intermediate III (90 mg, 0.41 mmol), PyBOP (281 mg, 0.54 mmol) and DIEA (0.14 ml, 0.81 mmol) in DCM/DMF (6 ml, 5:1) was stirred at 20C for 16 hr. The mixture was washed with sat. aq. NaHCO3, H2O, dried over MgSO4, evaporated and the brown residue was chromatographed on reverse phase HPLC (10-95% AcN in H2O) to give 8 (100 mg) as a brown solid. (Calculated mass: 386.4, observed mass: 386.5).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59290-81-2, 2-Methyl-5-nitro-3-pyridinecarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; KEMIA, INC.; WO2007/56016; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1079179-12-6, name is 2-Chloro-3-fluoro-5-nitropyridine, molecular formula is C5H2ClFN2O2, 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. name: 2-Chloro-3-fluoro-5-nitropyridine

To the reaction mixture of crude Compound 131 above was added 2- chloro-3-fluoro-5-nitropyridine (6 eq, 412 mg, 2.34 mmol) and CS2CO3 (6 eq, 763 mg, 2.34 mmol). The mixture was stirred at room temperature overnight and then partitioned between water and EtOAc. The organic phase was washed with aq saturated NaCl and concentrated. The residue was purified by silica gel column to give Compound 132.

With the rapid development of chemical substances, we look forward to future research findings about 1079179-12-6.

Reference:
Patent; EXELIXIS, INC.; BANNEN, Lynne Canne; BUI, Minna; JIANG, Faming; WANG, Yong; XU, Wei; (235 pag.)WO2019/148043; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem