Day: February 24, 2021

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

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

Application of 5470-17-7, 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.5470-17-7, name is 3-Bromo-2-chloro-5-nitropyridine, molecular formula is C5H2BrClN2O2, molecular weight is 237.44, as common compound, the synthetic route is as follows.

Example 16: Representative synthesis of Compound 201 Summary Compound 201 was synthesized via a seven-step route depicted below.Scheme: 36Ref: 1) Justus Liebigs Annalen tier Chemie, 1937, 529, 291 Experimental Step 1 To a solution of 3-bromo-2-chloro-5-nitropyridine (23.5g, 100 mmol ) in 200 mL of CH3OH was added CFbONa ( 54g , 1.0 mol ) with stirring in an ice bath. The resulting solution was heated at 80 C for 12 hrs and cooled to room temperature .The reaction mixture was diluted with 200 mL of H20 and extracted with ethyl acetate (3 x 250 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated to give a residue, which was purified by column chromatography over silica gel (50: 1 , petroleum ether/ EtOAc ) to afford a( 6.8 g, 34% ) as a yellow oil.

Statistics shows that 5470-17-7 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-2-chloro-5-nitropyridine.

Reference:
Patent; GENZYME CORPORATION; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; MAZITSCHEK, Ralph; CLARDY, Jon, C.; WIRTH, Dyann; WIEGAND, Roger; URGAONKAR, Sameer; BANIECKI, Mary, Lynn; CORTESE, Joseph; CELATKA, Cassandra; XIANG, Yibin; SKERLJ, Renato; BOURQUE, Elyse, M.j.; WO2011/53697; (2011); 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

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

Electric Literature of 39856-50-3 ,Some common heterocyclic compound, 39856-50-3, molecular formula is C5H3BrN2O2, 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.

1) 5-Bromo-2-nitropyridine (1 mol, 203 g) was dissolved in 1.5 L of dimethyl sulfoxide, and then an organically modified hectorite-supported ionic liquid material MHIL (40.6 g, 20 wt%) was added. Agitating and dispersing uniformly to obtain a first mixed liquid;2) Piperazine (129.2 g, 1.5 mol) was dissolved in 800 ml of dimethyl sulfoxide to form a piperazine solution, and then the piperazine solution was added dropwise to the first mixture to carry out a condensation reaction at 80 C;3) After 5 hours, the reaction solution was taken for HPLC detection (the percentage of 5-bromo-2-nitropyridine in the reaction solution was 0.08%, and the target product 1-(6-nitropyridin-3-yl)piperazine was 99.68%. Double condensation by-product 0.17%, the balance is unknown impurities), stop the reaction, use an organic microporous membrane with a pore size of 0.5 mum to filter and remove the organic modified hectorite-loaded ionic liquid material to obtain a filtrate;4) The filtrate is warmed to 60-65 C, and then the aqueous solution of methylamine at a concentration of 3 V% is added dropwise. When the turbidity occurs in the system, the dropwise addition is stopped, the mixture is kept warm for 20-30 min, and then the aqueous solution of methylamine having a concentration of 3 V% is continuously added dropwise. The concentration of 1-(6-nitropyridin-3-yl)piperazine in the solution was no longer decreased, and the temperature was naturally lowered to room temperature, filtered, and dried under vacuum at 45 C to obtain 197.4 g of a solid. The yield was 94.8%. 99.92% (external standard method); LC-MS: m/z = 209.1 [M+H].The ionic liquid material supported by the organic modified hectorite filtered by filtration was air-dried by acetone and recovered, and the yield of 1-(6-nitropyridin-3-yl)piperazine was 94.2%, and the content was 99.89%. Compared with the catalytic effect of fresh preparation, the catalytic material prepared by the invention can be recycled and used to reduce the production cost of the condensation step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,39856-50-3, its application will become more common.

Reference:
Patent; Zheng Chuanhua; Lu Xueling; Zhang Lei; (10 pag.)CN109369517; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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,
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.72587-15-6, name is 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine, molecular formula is C6H2ClF3N2O2, molecular weight is 226.54, as common compound, the synthetic route is as follows.COA of Formula: C6H2ClF3N2O2

2-Chloro-3-nitro-5-trifluoromethylpyridine (4.25 g, 18.8 mmol) was cooled to00C and diluted with ethyl 4-bromozincbutanoate (45 ml, 22.5 mmol, 0.5M in THF) under an atmosphere of nitrogen. PEPPSI-IPr (637 mg, 0.94 mmol) was added and the reaction was stirred at room temperature for 20 hours. The reaction was concentrated by evaporation and the dark residue was diluted with NH4Cl (20 ml, sat aq) and water (40 ml). Resulting suspension was extracted with EtOAC (4*25 ml) and combined organics were dried over MgSO4 and evaporated. The product was purified by flash chromatography using Pet. Ether/EtOAc (2/1) as eluent to give 850 mg (15 %) of ethyl 4-(3-nitro-5-(trifluoromethyl)pyridin-2-yl)butanoate as a brown oily mass.1H NMR (CDCl3): delta 9.01 (s, IH), 8.46 (s, IH), 4.13 (m, 3H), 3.22 (t, 2H, J= 7 Hz), 2.42 (t, 2H, J= 7Hz), 2.17 (m, 2H), 1.22 (m, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72587-15-6, 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Respiratorius AB; WO2009/7418; (2009); 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. 110651-92-8, name is 7-Chloro-6-nitrothieno[3,2-b]pyridine. A new synthetic method of this compound is introduced below., SDS of cas: 110651-92-8

A mixture of 1,4-dioxaspiro[4.5]decan-8-amine (from J&W PharmLab, 0.40 g, 2.5 mmol), 7-chloro-6-nitrothieno[3,2-b]pyridine (0.29 g, 1.4 mmol) and triethylamine (0.38 mL, 2.7 mmol) in isopropyl alcohol (4.4 mL) was stirred at 90 C. for 2 h. The mixture was concentrated to give the desired product to be used in the next step directly. LCMS calculated for C15H18N3O4S (M+H)+: m/z=336.1. Found: 336.0.

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, 110651-92-8, 7-Chloro-6-nitrothieno[3,2-b]pyridine.

Reference:
Patent; Incyte Corporation; Li, Yun-Long; Zhu, Wenyu; Mei, Song; Glenn, Joseph; US2014/121198; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 15862-37-0 ,Some common heterocyclic compound, 15862-37-0, molecular formula is C5H2Br2N2O2, 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: Methyl 4-(5-bromo-3-nitropyridin-2-yl)-3-fluorobenzoateTo a solution of (2-fluoro-4-(methoxycarbonyl)phenyl)boronic acid (0.5 00 g, 2.53mmol) and 2,5-dibromo-3-nitropyridine (0.7 12 g, 2.53 mmol) in THF (8.42 mL) wasadded aq. tripotassium phosphate (2M, 2.53 ml, 5.05 mmol). The reaction was degassedwith bubbling nitrogen, then PdC12(dppf)-CH2C12 adduct (0.124 g, 0.152 mmol) wasadded and the reaction was heated to 70 C for 2 h. The reaction was cooled, diluted withwater, and extracted 3 times with EtOAc. The combined organics were concentrated.The residue was purified via ISCO silica gel chromatography (40 g column; Hex/EtOAc;0 to 100%) to give methyl 4-(5-bromo-3-nitropyridin-2-yl)-3-fluorobenzoate (0.6 10 g,68%). ?H NMR (400MHz, CDC13) oe 9.01 (d, J2.1 Hz, 1H), 8.54 (d, J=2.1 Hz, 1H), 8.02(dd, J8.0, 1.5 Hz, 1H), 7.84-7.73 (m, 2H), 3.97 (s, 3H); LCMS (M+H) = 355.1; HPLC RT = 1.15 mm. Analytical HPLC Method 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15862-37-0, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem