Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 1086381-28-3, 4-Bromo-2-cyclopropylpyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a stirred solution of aryl bromide (4.42 mmol) in anhydrous DMF (16 mL) was added ethyl acrylate (5.75 mmol), Pd(OAc)2 (0.44 mmol), DABCO (8.84 mmol) and potassium carbonate (8.84 mmol). The solution was degassed under nitrogen for 15 min before heating to 125C for 17 h. The mixture was cooled, diluted with H2O (30 mL) and extracted into DCM (2 x 30 mL). The organic layers were washed with H2O (3 x 50 mL) and brine (2 x 50 mL), passed through a phase separator and concentrated. Following method D from 4-bromo-2-(cyclopropyl)pyridine (1 .00 g, 5.05 mmol). Purification by flash silica column chromatography (gradient elution /’-hex to 10% EtOAc in /-hex) gave the title compound as a white solid (530 mg, 48%). LCMS (ES+) 218 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1086381-28-3, 4-Bromo-2-cyclopropylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; CHDI FOUNDATION, INC.; LUCKHURST, Christopher A.; HAUGHAN, Alan F.; BRECCIA, Perla; STOTT, Andrew J.; BURLI, Roland W.; HUGHES, Samantha J.; MUNOZ-SANJUAN, Ignacio; DOMINGUEZ, Celia; MANGETTE, John E.; WO2012/103008; (2012); A1;,
Pyridine – Wikipedia,
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Related Products of 393-53-3 ,Some common heterocyclic compound, 393-53-3, molecular formula is C6H4FNO2, 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.

A 50 mL flask was charged with 5.0 g (0.0354 mol) 3-fluoroisonicotinic acid and thionyl chloride (3.88 mL, 0.053 mol). The mixture was heated to reflux for 1 h, then the excess thionyl chloride was evaporated under vacuum. Anhydrous methanol was added to the residue and the mixture was heated to reflux for one hour. The reaction mixture was poured into sodium bicarbonate solution and pH was adjusted to 7.0. The mixture was extracted with EtOAc and the organic layer was dry over sodium sulfate. The organic solvent was evaporated yielding the product (4.80 g, 88%). A 50 mL dry flask was charged with methyl 3-fluoroisonicotinitate (3.50 g, 0.0227 mol), 4-methoxyacetophenone (3.60 g, 0.024 mol) and 10 mL dry DMF under nitrogen. Sodium hydride (1.82 g, 60% in oil) was added and the reaction was stirred for 30 min, then poured into ammonium chloride solution and extracted with EtOAc and dried over sodium sulfate. The solution was concentrated and the residue was pass through a column (EtOAc:hexane 1:3) to give the product (3.50 g, 54.0%). A 50 mL flask was charged with this product (0.5 g, 1.75 mmol) and pyridine hydrogen chloride (2.02 g, 17.5 mmol) and heat to 190 C. for 4 h. The mixture was poured into a sodium bicarbonate solution and the solid was collected by filtration, washed with EtOAc and methanol to give 2-(4-hydroxyphenyl)-pyrano[2,3-c]pyridin-4-one as a yellow product (0.36 g, 86%). MS (ES) m/z: 240.90 (M+1), 239.89 (M); Mp. 294-296 C.

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. 393-53-3, 3-Fluoroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281396; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88312-64-5, Methyl 2-amino-5-nitronicotinate, 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, COA of Formula: C7H7N3O4, blongs to pyridine-derivatives compound. COA of Formula: C7H7N3O4

DMAP (0.744 g, 6.09 mmol, 0.1 equiv) and Boc2O (29.2 g,134 mmol, 2.2 equiv) were successively added portionwise toa suspension of 22 (12.0 g, 60.9 mmol) in freshly distilled THF (200 mL) at room temperature. The solution was stirred at room temperature for 4 h and evaporated in vacuo. The crude product was purified by flash chromatography using PE/DCM/Et3N (86:13:1,v/v/v) to give 23 (22.5 g, 93%) as a colourless solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88312-64-5, Methyl 2-amino-5-nitronicotinate, and friends who are interested can also refer to it.

Reference:
Article; Hedou, Damien; Deau, Emmanuel; Harari, Marine; Sanselme, Morgane; Fruit, Corinne; Besson, Thierry; Tetrahedron; vol. 70; 35; (2014); p. 5541 – 5549;,
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. 13603-44-6, name is 2,6-Dimethylpyridin-4-ol. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H9NO

2,6-Dimethyl-pyridin-4-yl trifluoromethanesulfonate (91)A suspension of pyridone 90 (5.0 g, 40.6 mmol) in DCM (100 mL) at 0C is treated with triethylamine (8.50 mL, 60.9 mmol) followed by trifluoromethane-sulfonic anhydride (10.2 mL, 60.9 mmol), added dropwise via syringe over 5 minutes. After warming to RT and stirring 2 h, the reaction mixture is washed with aqueous NaHCO3 (3 x 100 mL) and reduced in vacuo to afford the title compound. Yield: 9.25 g (quant.). LC/MS U 0.96 min. MS(ES+) m/z 256 (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, 13603-44-6, 2,6-Dimethylpyridin-4-ol.

Reference:
Patent; CURIS, INC.; WO2008/57497; (2008); A2;,
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.14667-47-1, name is Methyl 2-aminonicotinate, molecular formula is C7H8N2O2, molecular weight is 152.15, as common compound, the synthetic route is as follows.Computed Properties of C7H8N2O2

Preparation Example A-3 2-Amino-5-nitro-nicotinic acid methyl ester 2-Amino-nicotinic acid methyl ester (1.00g, 6.57mmol) described in Preparation Example A-2 was dissolved at 0C in a mixed solution of nitric acid (0.7mL) and sulfuric acid (2.6mL), which was stirred at 0C for 40 minute and at room temperature for 19 hours, then, further stirred at 70C for 4 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution at 0C, which was extracted with ethyl acetate and tetrahydrofuran, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo. Methanol was added to the residue, the precipitated solid was filtered to obtain the title compound (459mg, 2.33mmol, 35%) as a white solid. 1H-NMR Spectrum (DMSO-d6) delta (ppm): 3.86 (3H, s), 8.14 (1 H, brs), 8.62 (1 H, brs), 8.68 (1 H, d, J=2.7Hz), 9.04 (1 H, d, J=2.9Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14667-47-1, Methyl 2-aminonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1782811; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 15871-85-9, 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. 15871-85-9, name is 2-Methoxypyridine-5-carbonitrile. A new synthetic method of this compound is introduced below.

Step A: Preparation of 2-(6-Methoxypyridin-3-yl)propan-2-amine. fMethod Ll To a flame dried flask containing cerium(III) chloride (4.59 g, 18.64 mmol) was addedTHF (60 mL) under nitrogen atmosphere. The suspension was stirred at room temperature for 2 h, cooled down below -50 0C, then added methyllithium (11.65 mL, 18.64 mmol) in hexanes. The whole reaction mixture was stirred for 30 min at that temperature, and 6- methoxynicotinonitrile (0.5 g, 3.73 mmol) in THF (2 mL) was added. The cooling bath was removed, and the reaction was stirred at room temperature for 18 h, quenched with concentrated NH4OH (15 mL) at below -40 0C. The mixture was brought to 25 0C and filtered through Celite. The solid was washed with 10% MeOH/CH2Cl2. The combined filtrates were concentrated, and the residue was purified by HPLC. The fractions collected were neutralized with saturated NaHCO3, then extracted with 1:4 iPrOH/CH2Cl2. The organics were dried and concentrated to give the title compound (180 mg). LCMS mlz = 167.3 [M+H]+; 1H NMR (400 MHz, CDCl3) delta ppm 1.50 (s, 6H), 3.92 (s, 3H), 6.71 (d, J= 8.7 Hz, IH), 7.75 (ddd, J= 1.4, 2.6 and 8.7 Hz, IH), 8.29 (dd, J= 1.4 and 2.6 Hz, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15871-85-9, its application will become more common.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; THORESEN, Lars; JUNG, Jae-Kyu; STRAH-PLEYNET, Sonja; ZHU, Xiuwen; XIONG, Yifeng; YUE, Dawei; WO2011/25541; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 131747-45-0, 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.131747-45-0, name is (4-Bromopyridin-2-yl)methanol, molecular formula is C6H6BrNO, molecular weight is 188.02, as common compound, the synthetic route is as follows.

General procedure: Freshly prepared Ag2O (2.20 mmol) was added at room temperature to a solution of pyridin-2-ylmethanol (1.00 mmol) and 2-iodopropane (2.20 mmol) in 1,4-dioxane (10 mL) and stirred for 24 h. The reaction mixture was filtered through a Celite bed and washed with ethyl acetate. Filtrate was concentrated under vacuum.The resulting material was purified by flash chromatography on a Biotage instrumentusing 4-g flash cartridge and eluted with 12-15% ethyl acetate in hexane to give isopropyl picolinate (2) (65% yield).

The chemical industry reduces the impact on the environment during synthesis 131747-45-0, I believe this compound will play a more active role in future production and life.

Reference:
Article; Patil, Vikas S.; Reddy, M. Rajendar; Pal, Shyam Sundar; Sharma, Somesh; Reddy, L. Krishnakanth; Synthetic Communications; vol. 44; 14; (2014); p. 2121 – 2127;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 84249-14-9 , The common heterocyclic compound, 84249-14-9, name is 2-Amino-4-bromopyridine, molecular formula is C5H5BrN2, 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.

To a solution of potassium 2-chloro-3 -ethoxy-3 -oxoprop-l-en-l-olate (13.0 g, 68.9 mmol) and 4-bromopyridin-2-amine (3.00 g, 17.3 mmol) in ethanol (60 mL) was added cone. H2SO4 (2 mL). The reaction mixture was stirred at 90 C for 18 h and concentrated in vacuo. The residue was adjusted to pH = 10 with a saturated NaHCO, aqueous solution, and extracted with EtOAc (200 mL x 3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2S04, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/PE (v/v) = 1/4) to give the title compound as a white solid (4.6 g, 99%).MS (ESI, pos. ion) m/z: 269.1 [M+H]+;1H NMR (400 MHz, CDCb): d (ppm) 9.17 (d, J= 7.3 Hz, 1H), 8.26 (s, 1H), 7.92 (d, 7= 1.1 Hz, 1H), 7.14 (dd, J= 7.3, 1.6 Hz, 1H), 4.41 (q, J= 7.1 Hz, 2H), 1.42 (t, J= 7.1 Hz, 3H).

The synthetic route of 84249-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 929617-35-6, 5-Bromo-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, 929617-35-6, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a solution of (R)-5-(2-hydroxy-l-phenylethyl)-amino)-pyridin-3-yl)-boronic acid (149 mg, 0.75 mmol) in DME/H20 (5: 1, 6 mL) was added Pd(PPh3)4 (173 mg, 0.15 mmol), K2C03 (207 mg, 1.5 mmol) and 5-bromo-lH-pyrazolo[3,4-c]pyridine (193.5 mg, 0.75 mmol). The resulting mixture was degassed and then stirred for 10 hours at 95 C under an Ar atmosphere. After cooling, the mixture was diluted with water (30 mL) and then extracted with EtOAc (2 x 50 mL). The combined organic layers were washed with water and brine, and then dried. The solvent was concentrated and the residue was purified by Prep-HPLC to give (R)-2-phenyl-2-[5- (lH-pyrazolo[3,4-c]pyridin-5-yl)-pyridin-3-ylamino]-ethanol (8 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,929617-35-6, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; YANG, Song; ZHOU, Chengang; WO2014/90692; (2014); 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. 131747-63-2, name is 4-Bromopicolinaldehyde. A new synthetic method of this compound is introduced below., Safety of 4-Bromopicolinaldehyde

Example 30i 4-Bromo-2-(difluoromethyl)pyridine Diethylaminosulphur trifluoride (4.08 mL, 33.31 mmol) was added to 4-bromopicolinaldehyde (0.267 M in chloroform) (100 mL, 26.7 mmol) at 0 C. under an atmosphere of argon. The reaction mixture was stirred over night while the temperature was raised to room temperature. The reaction was quenched by addition of aqueous sodium bicarbonate (sat.) and was further diluted with dichloromethane. The solids were filtered off through a pad of Celite. The organic layer was collected and the water phase was extracted with dichloromethane (*3). The organic layers were pooled, dried (Na2SO4), filtered and concentrated. Purification by silica chromatography using 0 to 60% diethyl ether in pentane gave the title compound (1.78 g, 32%). 1H NMR (400 MHz, DMSO-d6) delta ppm 8.59 (d, 1H) 7.98 (d, 1H) 7.90 (dt, 1H) 6.98 (t, 1 H); MS (APCI+) m/z 208, 210 [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, 131747-63-2, 4-Bromopicolinaldehyde.

Reference:
Patent; ASTRAZENECA AB; US2010/125082; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem