Day: January 13, 2021

Synthetic Route of 102830-75-1, Adding some certain compound to certain chemical reactions, such as: 102830-75-1, name is 3-Bromo-5-chloro-2-methoxypyridine,molecular formula is C6H5BrClNO, 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 102830-75-1.

EXAMPLE 4 A solution of 4.0 g of 3-bromo-5-chloro-2-methoxypyridine in 75 ml of anhydrous ether was cooled to -70 C. under nitrogen. The resulting slurry was stirred rapidly and there was added 12.0 ml of 1.65M n-butyllithium/hexane dropwise over a period of about 5 minutes while keeping the temperature below -70 C. The reaction mixture became homogeneous and, after 15 minutes, a solution of 3.0 g of 4-chlorocinnamaldehyde in 35 ml of ether was added dropwise while keeping the temperature below -60 C. The cold mixture was then poured into aqueous saturated sodium bicarbonate solution and the resulting mixture was extracted with ether. The ether layer was washed with aqueous saturated sodium chloride solution, dried over potassium carbonate and concentrated under reduced pressure to give a white solid. This solid was recrystallized from a mixture of ethyl acetate/hexane to give (E)-5-chloro-alpha-[2-(4-chlorophenyl)ethenyl]-2-methoxy-3-pyridinemethanol as white needles melting at about 135-139.5

According to the analysis of related databases, 102830-75-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merrell Dow Pharmaceuticals Inc.; US4588733; (1986); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16133-25-8, 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 16133-25-8 as follows.

Example 64Pyridine-3-sulfonic acid [3-(4,4-dimethyl-6-trifluoromethyl-l,2,3,4-tetrahydro- quinolin-2-yl)-phenyl]-amideTo a stirred solution of 3-(4,4-dimethyl-6-trifluoromethyl-l,2,3,4-tetrahydro-quinolin-2-yl)- phenylamine (150 mg, 0.47 mmol) in pyridine (0.74 mg, 0.94 mmol) and dichloromethane (3 mL) at 0¡ãC was added dropwise a solution of pyridine-3-sulfonyl chloride (100 mg, 0.56 mmol) in dichloromethane (1 mL). The mixture was stired at room temperature overnight. Thin layer chomatography and LC-MS indicated that 3-(4,4,6-trimethyl-l,2,3,4-tetrahydro- quinolin-2-yl)-phenylamine was consumed completely. The mixture was quenched with water (5 mL) and extracted with dichloromethane (5 mL x 2). The combined organic layers were dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chomatography on silica gel to afford pyridine-3 -sulfonic acid [3-(4,4-dimethyl-6- trifluoromethyl-l,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-amide (170 mg, 78.7percent) as a white solid. MS (ESI+APCI) M+l=442.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16133-25-8, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FENG, Lichun; HUANG, Mengwei; LIU, Yongfu; WU, Guolong; ZHOU, Mingwei; WO2012/52372; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 61160-18-7 , The common heterocyclic compound, 61160-18-7, name is 3-(Benzyloxy)-2-methylpyridin-4(1H)-one, molecular formula is C13H13NO2, 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.

Synthesis of iron chelator-nanoparticle systems: The general synthesis of the chelator 1 is described in scheme 3.86 Scheme 3. R=Me, Et. a: benzylchloride/NaOH/. b: NH4OH. C: hexamethyldisilazane/chlorotrimethylsilane/(2-acetoxyethoxy)methyl bromide, trimethylsilyl trifluoromethanesulfonate in 1,2-dichloroethane. c: basic hydrolysis with NH4OH. d: tosyl chloride in pyridine. e: nanoparticles with amino functional groups. f: BBr3/CH2Cl2 at 4¡ã C. for 30 min. Instead of benzyloxyethoxymethylchloride, 2-acetoxyethoxy)methyl bromide is used and the synthetic method is the same as described herein. The acetyl protection group on the side chain is removed by basic hydrolysis in methanolic ammonia solution. The mixture is stirred at room temperature in a sealed flask for 24 h. After purification by silica gel chromatography using CHCl3-MeOH (8:1) as an eluent, the deprotected hydroxyl group is converted into P-toluene-sulphonyl (tosyl) ester by the reaction with tosyl chloride (1.1 moles per mole of chelator) in dry pyridine. After removal of the solvent, the crude ester is often used directly. Before conjugation, 1 mL (100 mg/mL) of amino-modified nanoparticles are washed in 10 mL of 0.1 M sodium phosphate buffer (pH 7.4). After second wash, resuspend pellet in 10 mL of tosyl activeted chelator solution, ensuring that the particles are completely suspended by vortexing. Allow to react at 37¡ã C. for 24 hours with continuous mixing. Separate the particles conjugated with chelators by centrifugation and wash with phosphate buffered saline (pH 7.4) four times. Then, deprotect OH on pyridinone ring by BBr3 in CH2Cl2 at 4¡ã C. with shaking for 30 min. The new chelator-particle system is obtained by centrifugation and wash four times with PBS buffer. Resuspend in 10 mL 25 mM Tris buffer (pH 7.4) and store at 4¡ã C. until used. As mentioned above, if the nanoparticles could be damaged during the deprotective step, we will use an altered method to conjugate the chelator. The toluene sulfonic group (Tosyl-O-group) may be changed into an amino group by nucleophilic displacement reaction. To obtain primary amines in reasonable yield, sufficient excess ammonia is used. After that, first, deprotection of the OH group on the pyridinone ring by using the same deprotective method as above, then conjugate the chelator to Sulfo-NHS(N-hydroxysulfosuccinimide) preactivited carboxylic acid functinal nanoparticles just like chelators 2, 3, and DFO do. The chelator concentrations of the reaction solution before and after conjugation are determined by using UV-visible spectroscopy or HPLC, thereby the amount of the chelator conjugated to nanoparticles can be obtained by simply multiplying the difference of the concentrations with the reaction volume.

The synthetic route of 61160-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Utah Research Foundation; US2006/30619; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 582325-22-2 ,Some common heterocyclic compound, 582325-22-2, molecular formula is C12H8FNO2, 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 6-(3-fluorophenyl)nicotinic acid (391 mg, 1.8 mmol ) in DMF (10 mL) at 0 C. was added HATU (753 mg, 1.98 mmol) and DIPEA (0.47 mL, 2.07 mmol ). After 15 min, cis-tert-butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate was added and the reaction stirred at room temperature for 5 hrs. The solvent was removed in vacuo and the residue diluted with ethyl acetate and water. The layers were separated and the organic layer washed with brine, dried (MgSO4) and the solvent removed to give an oil, which after chromatography (silica, 65% ethyl acetate:hex) to give the desired product, cis -tert-butyl-3-({[6-(3-fluorophenyl)pyridin-3-yl]carbonyl}amino)-4-hydroxypyrrolidine-1-carboxylate (420 mg, 58%). LC/MS (M+H)=401.9 observed, 402.18 expected.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,582325-22-2, its application will become more common.

Reference:
Patent; Blake, Tanisha D.; Hamper, Bruce C.; Huang, Wei; Kiefer, James R.; Moon, Joseph B.; Neal, Bradley E.; Olson, Kirk L.; Pelc, Matthew J.; Schweitzer, Barbara A.; Thorarensen, Atli; Trujillo, John I.; Turner, Steven R.; US2008/146569; (2008); 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. 18653-75-3, name is 2-(1H-Imidazol-2-yl)pyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C8H7N3

The synthetic routes for the ligand L1 (white color) were reported in our previous work [15]. The ligand L2 (white color) was obtained by refluxing 2-(pyridin-2-yl) imidazole (obtained commercially from Aldrich and used as received) with ethylchloroacetate under basic conditions (Supporting information, Scheme 1) [23]. Yield ca. 90%. M.p.: 120-121C. Elemental Analysis (%) for L2 (C11H13O2N3), calcd: C, 60.24; H, 5.97; N, 19.17. Found: C, 60.37; H, 5.84; N, 19.06%. IR (KBr, cm-1): 3050, 2978, 2375, 2289, 1580, 1564, 1530, 1486, 1345, 1266, 1240, 1150, 1060, 1025, 980, 969, 790, 740, 725. 1H NMR delta, ppm: 1.30 (m, 3H), 4.12 (m, 2H), 4.7 (2, 2H), 6.88 (d, 1H), 7.15 (d, 1H), 7.4-8.5 (m, 4H). 13C NMR delta, ppm: 14.6, 48.4, 62.1, 120.5, 124.3, 128.5, 131.4, 137.2, 149.2, 155.6, 162.7.

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, 18653-75-3, 2-(1H-Imidazol-2-yl)pyridine.

Reference:
Article; Luo, Yang-Hui; Wen, Gao-Ju; Gu, Lian-Shuai; Wang, Man-Ning; Sun, Bai-Wang; Polyhedron; vol. 121; (2017); p. 101 – 106;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 18368-64-4, 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. 18368-64-4, name is 2-Chloro-5-methylpyridine. A new synthetic method of this compound is introduced below.

2-Chloro-5-methyl-4-nitropyridine N-oxide () : Following the method of Z. Talik, A. Puszko, Roczniki Chemii Ann. Soc. Chim. Polonorum, 1976, 50, 2209, to a suspension of 2-chloro-5-methylpyridine (10 g, 0.078 mol) in acetic anhydride (25 mL), hydrogen peroxide 30% (25 mL) was added in small portions. This mixture was stirred at room temperature for 24 hours and then heated at 60 C for 30 hours. After removing the excess of acetic acid under reduced pressure, the residue was added in small portions to concentrated sulfuric acid (15 mL). The resulting solution was added to a mixture of concentrated sulfuric acid (15 mL) and fuming nitric acid (25 mL), and then heated at 100 C for 90 minutes. The reaction mixture was poured on ice, neutralized with solid ammonium carbonate and finally with aqueous ammonia until basic. A precipitate was then formed. After nitration, 10 was isolated as a pale yellow solid (9.4 g, 0. 050 mol, HPLC Rt 3.272 minutes, FIA ES+ 188.9, ES-188.0).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-64-4, 2-Chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2003/91246; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 586-95-8 ,Some common heterocyclic compound, 586-95-8, molecular formula is C6H7NO, 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.

(4) 4-pyridine methanol was reacted with thionyl chloride (26.18 g, 0.22 mol) in methanol solution, and traced by thin layer chromatography. After the reaction was completely converted to 4-chloromethylpyridine hydrochloride, the reaction was stopped. After suction filtration, the product was obtained in a yield of 26.9 g (yield: yield)

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. 586-95-8, 4-Pyridinemethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Danyang Ning David Fang To Detect Co., Ltd.; Wei Qian; (5 pag.)CN109761888; (2019); A;,
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. 897732-75-1, name is 2-Methyl-6-(methylsulfonyl)pyridin-3-amine, molecular formula is C7H10N2O2S, 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. HPLC of Formula: C7H10N2O2S

Example 84-[4-(6-Methanesulfonyl-2-methyl-pyridin-3-ylamino)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester; A mixture of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 50 mg, 0.15 mmol), 6-methanesulfonyl-2-methyl-pyridin-3-ylamine (Intermediate 4; 28 mg, 0.15 mmol), palladium acetate (0.33 mg, 0.01 equivalent), sodium tert-butoxide (34 mg, 0.36 mmol), and 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (Aldrich, 1 mg, 0.02 equivalents) in dimethylformamide (2 mL) was heated in the microwave oven at 160 C. for 10 min. Ethyl acetate and water were added, and the aqueous layer was extracted three times with ethyl acetate. The ethyl acetate layers were combined, evaporated, and purified by preparative C18 HPLC, eluting with 10-100% acetonitrile/water. Samples containing the product were extracted twice with dichloromethane and the solvent was evaporated under high vacuum to give 4-[4-(6-methanesulfonyl-2-methyl-pyridin-3-ylamino)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (34 mg, 46%) as a white powder. 1H NMR (300 MHz, DMSO-d6) delta 1.41 (s, 9H), 1.92-2.00 (m, 4H), 2.55 (s, 3H), 2.90-3.04 (m, 2H), 3.30 (water peak and SO2CH3 peak), 4.00-4.12 (m, 2H), 4.84-4.96 (m, 1H), 7.92 (d, 1H, J=8.5 Hz), 8.22-8.36 (m, 3H), 10.06 (br s, 1H). HRMS Calcd. for C22H30N7O4S (MH+): 488.2075. Found: 488.2073.

With the rapid development of chemical substances, we look forward to future research findings about 897732-75-1.

Reference:
Patent; Erickson, Shawn David; Gillespie, Paul; Guertin, Kevin Richard; Karnachi, Prabha Saba; Kim, Kyungjin; Ma, Chun; McComas, Warren William; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Tilley, Jefferson Wright; Zhang, Qiang; US2009/286812; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52718-95-3, 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 52718-95-3, name is Methyl 2-bromonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

Part D. Preparation of methyl 2-(3′-cyanophenyl)nicotinate. Methyl 2-bromonicotinate (2.0 g, 9.3 mmol) and 3-cyanophenylboronic acid (2.7 g, 18.4 mmol) were combined in 190 mL benzene. Sodium carbonate (19 mL of a 2 M aqueous solution), tetrabutylammonium bromide (152 mg, 0.5 mmol), and bis(triphenylphosphine)palladium(II) chloride (325 mg, 0.5 mmol) were added. The entire mixture was evacuated to remove dissolved gasses, then placed under argon. The reaction was refluxed for 14 hours, diluted with water and EtOAc, separated, dried over Na2 SO4, filtered, and evaporated. The resulting yellow solid was chromatographed on silica gel (30% EtOAc/hexanes) to yield a light yellow solid (1.70 g, 77%). 1 H NMR (CDCl3): delta 8.81 (dd, 1H, J=4.8, J’=1.8), 8.23 (dd, 1H, J=8.0, J’=1.9), 7.85 (s, 1H), 7.73 (m, 2H), 7.55 (t, 1H, J=7.7), 7.43 (m, 1H), 3.76 (s, 3H).

According to the analysis of related databases, 52718-95-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dupont Pharmaceuticals; US6060491; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 77992-44-0 , The common heterocyclic compound, 77992-44-0, name is (5-Bromopyridin-2-yl)hydrazine, molecular formula is C5H6BrN3, 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 mixture of [5-BROMO-PYRIDIN-2-YL-HYDRAZINE] (4.34 g, 23.1 [MMOL)] and isobutyryl chloride (21.8 mL, 0.208 mol) is refluxed gently for 3 hours. The mixture is then cooled to room temperature. Hexane (22.0 mL) is added and the resulting slurry stirred at room temperature for 15 minutes and filtered. The filtrate cake is washed with hexane (3x) and dried in a vacuum-oven (30-35 [C)] for 48 hours. The product (5.90 g, yield 92.3%) may be obtained as an off-white powder. A biphasic mixture of the product (5.87 g, 21.2 [MMOL),] water (12.0 mL) and dichloromethane (18.0 mL) is cooled to 5 to [10 C.] A 1N aqueous solution of [NAOH] (21.5 mL) is added over a period of 10 minutes. The mixture is stirred in the bath for 15 minutes. The organic layer is isolated and the aqueous layer extracted with [DICHLOROMETHANE] (2x). The combined organic extracts are washed with 1: 1 brine-water and dried [(MGS04).] Most of the [DICHLOROMETHANE] is removed in vacuo. Ethyl acetate (8.0 mL) is added. After removing about half of the solvent, hexane (32.0 mL) is added. The slurry is stirred in an ice-water bath for 2 hours and filtered. The cake is washed with 9: 1 hexane-ethyl acetate (3x) and dried in a vacuum-oven (30-35 [C)] for 18 hours. The title compound may be obtained as a sandy tan powder (4. 72g, 92.5%).

The synthetic route of 77992-44-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/20440; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem