Tag: M.W:100-200

Electric Literature of 717106-69-9 , The common heterocyclic compound, 717106-69-9, name is Methyl 2-(6-chloropyridin-3-yl)acetate, molecular formula is C8H8ClNO2, 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.

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed methyl 2-(6-chloropyridin-3-yl)acetate (1.86 g, 10.0 mmol, 1.00 equiv), toluene (50 mL), Cs2CO3 (10.0 g, 30.0 mmol, 3.00 equiv), 1-benzylpiperazine (2.11 g, 12.0 mmol, 1.2 equiv), and RuPhosPd (0.39 g, 0.05 equiv). The resulting solution was stirred for 10 hours at 100 C. in an oil bath. The reaction mixture was cooled to room temperature. The reaction was then quenched by the addition of water (50 mL). The resulting solution was extracted with ethyl acetate (100 mL*2), and the organic layers were combined. The resulting mixture was washed with brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (v:v=1/3). This resulted in 1.1 g (32%) of methyl 2-[6-(4-benzylpiperazin-1-yl)pyridin-3-yl]acetate as a yellow solid.

The synthetic route of 717106-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arvinas Operations, Inc.; Genentech, Inc.; Crew, Andrew P.; Wang, Jing; Berlin, Michael; Dragovich, Peter; Chen, Huifen; Staben, Leanna; US2019/300521; (2019); 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.37669-64-0, name is 5-Bromo-3-pyridinemethanol, molecular formula is C6H6BrNO, molecular weight is 188.02, as common compound, the synthetic route is as follows.category: pyridine-derivatives

To a solution of (5-bromopyridin-3-yl)methanol (3 g, 16.0 mmol) in DCM (15 mL) cooled to 0 C. was added thionylchloride (7.59 g, 63.8 mmol) dropwise and the reaction mixture was stirred at room temperature over night. The mixture was poured onto ice/water (20 mL), basified with NaOH conc. (8 mL) and extracted with EtOAc (2×50 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40% EtOAc-Heptane gradient to give the title compound (3.08 g, 93%) as a white solid. MS: 206.0, 207.9 (M+H+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,37669-64-0, 5-Bromo-3-pyridinemethanol, and friends who are interested can also refer to it.

Reference:
Patent; Aebi, Johannes; Amrein, Kurt; Hornsperger, Benoit; Knust, Henner; Kuhn, Bernd; Liu, Yongfu; Maerki, Hans P.; Mayweg, Alexander V.; Mohr, Peter; Tan, Xuefei; Zhou, Mingwei; US2013/72679; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74409-42-0 ,Some common heterocyclic compound, 74409-42-0, molecular formula is C8H11NO, 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.

2,3,5-trimethylpyridine 1-oxide (1.38 kg, 10.1 mol) was charged into 98% sulfuric acid (4.93 kg, 49.3 mol). 97% nitric acid (1.44 kg) was added dropwise to the solution over 50 minutes, and the solution was then heated for 4 hours at 85C. The reaction solution was charged into a mixture of ammonium hydrogencarbonate (10.6 kg) and water (9.0 L), and the resultant mixture was extracted with ethyl acetate (3.0 L × 3). The resultant organic layer was concentrated and then dried overnight under vacuum to obtain 1.50 kg of the title compound.

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. 74409-42-0, 2,3,5-trimethylpyridine 1-oxide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1875911; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 271-47-6, 1H-Pyrazolo[3,4-c]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, HPLC of Formula: C6H5N3, blongs to pyridine-derivatives compound. HPLC of Formula: C6H5N3

To a solution of 1H-pyrazolo[3,4-c]pyridine (4.0 g, 33.6 mmol, 1.0 eq.) in DMF(40 mL) were added K2C03 (9.3 g, 100.8 mmol, 3.0 eq.), ?2 (7.9 g, 33.6 mmol, 1.0 eq.). Theresulting mixture was stirred at r.t. for 3 hr, then diluted by H20 and filtered. The collectedsolid was dried to give 3-iodo-1H-pyrazolo[3,4-c]pyridine (6.0 g, 73.0 %).

The synthetic route of 271-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIFESCI PHAMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (241 pag.)WO2017/98328; (2017); A2;,
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. 17874-79-2, name is 5-(Methoxycarbonyl)picolinic acid, the common compound, a new synthetic route is introduced below. name: 5-(Methoxycarbonyl)picolinic acid

Reference Example 2 N-(2-t-Butoxycarbonylaminophenyl)-5-methoxycarbonylpyridine-2-carboxylic acid amide (Reference Compound No.2-1) HATU (21 g, 55 mmol) was added to a solution of 2-aminophenylcarbamic acid t-butyl ester (Reference Compound No.1-1, 10 g, 50 mmol), 5-methoxycarbonylpyridine-2-carboxylic acid (10 g, 55 mmol), and N-methylmorpholine (11 mL, 100 mmol) in DMF (100 mL), and then the reaction mixture was stirred at room temperature for 20 hours. Water (300 mL) was added thereto, and then the whole was extracted with ethyl acetate (300 mL) three times. The organic layer was washed with brine (200 mL), and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the obtained solid was collected by filtration to give 15 g of the title reference compound as a pale brown solid. (Yield 79%) 1H-NMR (400 MHz, CDCl3) delta 1.53 (s, 9H), 4.01 (s, 3H), 6.90 (br s, 1H), 7.20-7.25 (m, 2H), 7.51 (m, 1H), 7.82 (m, 1H), 8.38 (dd, J = 8.1, 0.7 Hz, 1H), 8.50 (dd, J = 8.1, 2.1 Hz, 1H), 9.18 (dd, J = 2.1, 0.7 Hz, 1H), 10.28 (br s, 1H)

The synthetic route of 17874-79-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Santen Pharmaceutical Co., Ltd; EP2133339; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 180748-30-5, name is (4-Chloropyridin-2-yl)methanamine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 180748-30-5

[0411] To (4-chloro-2-pyridyl)methanamine (59, 0.51 g, 3.58 mmol) in dichloromethane (50 mL) was added l-isothiocyanato-4-nitro-benzene (65, 0.66 g, 3.65 mmol). The reaction mixture was stirred at room temperature for about 1 hour. LCMS showed the reaction was complete. The reaction was concentrated, and washed with ethyl acetate and hexane to give product (63).

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, 180748-30-5, (4-Chloropyridin-2-yl)methanamine.

Reference:
Patent; PLEXXIKON INC.; ZHANG, Jiazhong; POWERS, Hannah; ALBERS, Aaron; PHAM, Phuongly; WU, Guoxian; BUELL, John; SPEVAK, Wayne; GUO, Zuojun; WALLESHAUSER, Jack; ZHANG, Ying; (229 pag.)WO2019/183145; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 42753-71-9, name is 2-Amino-5-bromo-6-methylpyridine. A new synthetic method of this compound is introduced below., Computed Properties of C6H7BrN2

Example A3 A 0 C. solution of sulfuric acid (125 mL) was treated drop-wise with H2O2(30%, 63.1 mL, 2058 mmol), stirred for 15 min, treated drop-wise with a cold solution of 6-amino-3-bromo-2-picoline (35 g, 187 mmol) in sulfuric acid (125 mL), allowed to warm to RT and stirred for 4 h. The mixture was poured onto ice (1.2 kg) and the resulting solid collected via filtration, dissolved in DCM, washed with brine, dried over Na2SO4 and concentrated to dryness. The aqueous filtrate and washes were combined, extracted with DCM (2*) and the combined organics were dried over Na2SO4, concentrated to dryness, purified via silica gel chromatography (EtOAc/Hex) and combined with the above-isolated solid to afford 3-bromo-2-methyl-6-nitropyridine (25.59 g, 63%). MS (ESI) m/z: 218.9 (M+H+).

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, 42753-71-9, 2-Amino-5-bromo-6-methylpyridine.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Kaufman, Michael D.; Patt, William C.; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Yates, Karen M.; US2014/275080; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3939-13-7, 2-Fluoronicotinonitrile, 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 C6H3FN2, blongs to pyridine-derivatives compound. Computed Properties of C6H3FN2

Synthesis of intermediate VX001: Isoxazolo[5,4-b]pyridin-3-amine 909 mg (8.1 mmol) of KO-t-Bu were added, with vigorous stirring, to a suspension of 668 mg (8.9 mmol) of acethydroxamic acid in DMF (20 ml), and the mixture was stirred for 30 min at RT. 990 mg (8.1 mmol) of 2-fluoro-nicotinonitrile were then added, and stirring was carried out for a further 5 h at 50 C. The mixture was then extracted with EA and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 7:3) of the residue yielded 305 mg (2.3 mmol, 28%) of isoxazolo[5,4-b]pyridin-3-amine.

The synthetic route of 3939-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUNENTHAL GMBH; US2010/234419; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 139022-25-6, 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. 139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid, molecular formula is C8H6N2O2, 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.

(5-((3-bromophenoxy)methyl)-4,5-dihydroisoxazol-3-yl)methanamine hydrochloride (±) (0.300 g, 0.932 mmol) was reacted with imidazo[l,2-a]pyridine-6-carboxylic acid (0.181 g, 1.119 mmol) in the presence of BOP reagent (0.452 g, 1.025 mmol) and Nu,Nu- diisopropylethylamine (0.359 g, 2.790 mmol) in Nu,Nu-dimethylformamide (10 mL) at room temperature for 16 h. The reaction mixture was diluted with water (10 mL) extracted with ethyl acetate (50 mL) and washed with water (4 x 50 mL). The organic phase was dried over sodium sulfate and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel (methanol/dichloromethane = 2/98) to give titled compound (0.250 g, 62 %) as a solid. LCMS: m/z 429.3 [M+H] +; lU NMR (300 MHz, Chloroform-d) delta 8.83 (m, 1H), 7.73 – 7.62 (m, 3H), 7.44 (dd, / = 9.4, 1.8 Hz, 1H), 7.15 – 7.04 (m, 2H), 6.90 – 6.79 (m, 2H), 5.07 – 4.98 (m, 1H), 4.43 (d, / = 5.3 Hz, 2H), 4.06 (d, / = 4.7 Hz, 2H), 3.25 (dd, / = 17.3, 10.7 Hz, 1H), 3.09 (dd, / = 17.3, 7.2 Hz, 1H).

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 139022-25-6, Imidazo[1,2-a]pyridine-6-carboxylic acid.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; PANIGRAHI, Sunil Kumar; WO2014/111871; (2014); 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.58584-63-7, name is (6-Methoxypyridin-3-yl)methanol, molecular formula is C7H9NO2, molecular weight is 139.15, as common compound, the synthetic route is as follows.Quality Control of (6-Methoxypyridin-3-yl)methanol

To a stirred solution of (6-methoxypyridin-3-yl)methanol (49.8 mg, 0.358 mmol) in DMF (0.5 ml.) at 0 C was added sodium hydride (60% dispersion in mineral oil) (10.73 mg, 0.447 mmol) and the reaction mixture stirred for 15 min prior to the addition of 4- methylbenzene-l-sulfonyl chloride (85 mg, 0.447 mmol). The reaction was stirred for a further 30 min at this temperature. In a separate flask, 5-(4-chloro-lH-imidazol-2-yl)-l,3- dimethylpyridin-2(lH)-one (for an example preparation, see Intermediate 12, 40 mg, 0.179 mmol) was dissolved in DMF (0.5 ml.) at 0 C, to which sodium hydride (60% dispersion in mineral oil) (8.58 mg, 0.358 mmol) was added and the reaction stirred for a further 30 min. The solution containing the tosylated pyridine was added dropwise to the flask containing the imidazole, and the reaction stirred for a further 16 h. The solvent was removed in vacuo and the crude product was purified by MDAP (Method A) to afford the title compound as a colourless film (16 mg, 0.04 mmol, 23%). LCMS (System A): tRET = 0.79 min; MH+ 345.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58584-63-7, (6-Methoxypyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BAXTER, Andrew; BIT, Rino, Antonio; BROWN, John, Alexander; HIRST, David; HUMPHREYS, Philip; JONES, Katherine, Louise; PATEL, Vipulkumar, Kantibhai; (124 pag.)WO2018/41964; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem