Month: April 2022

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. 884494-52-4, name is 3-Bromo-2-fluoro-4-iodopyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-2-fluoro-4-iodopyridine

Isopropylmagnesium chloride, 2 M solution in THF (0.814 mL, 1.63 mmol) was added dropwise over 15 minutes to a degassed solution of 3-bromo-2-fluoro-4-iodopyridine (0.468 g, 1.55 mmol) in Et2O (0.150 mL) and THF (0.850) cooled at -78 0C. The solution was stirred for 0.5 h. Zinc chloride, 1.0 M solution in diethyl ether (0.776 mL, 0.776 mmol) was then added dropwise to the reaction over 10 minutes. The reaction was allowed to reach room temperature. The reaction warmed to room temperature within 15 min. A solution of compound 238 (0.150 g, 0.517 mmol) and tetrakis(triphenylphosphine)palladium (0.0418 g, 0.0362 mmol) in THF (0.50 mL) was added to the reaction. The reaction was equipped with a reflux condenser and stirred in a 60 0C oil bath. After 2 h the reaction was removed from heat and allowed to stand overnight. Saturated NH4Cl (0.5 mL) and 12% 2-propanol in CH2Cl2 (2 mL) were added. The organics were sequestered and the aqueous was extracted with 12% 2- propanol in CH2Cl2 (4 x 4 mL). The combined organics were washed with brine, dried over MgSO4, and concentrated in vacuo. Silica gel chromatography (elution 3% methanol in DCM with 0.175 % NH4OH additive) afforded compound 240 (0.140 g, 80.1% yield). 1H NMR (500 MHz, CDCl3) delta ppm 0.22 (d, J= 4.40 Hz, 2 H) 0.46 – 0.59 (m, 2 H) 0.96 – 1.07 (m, 1 H) 3.21 – 3.36 (m, 2 H) 4.51 (br. s., 1 H) 5.11 (br. s., 2 H) 7.16 (d, J= 4.89 Hz, 1 H) 7.69 (s, 1 H) 8.22 (d, J= 4.89 Hz, 1 H) ppm.

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, 884494-52-4, 3-Bromo-2-fluoro-4-iodopyridine.

Reference:
Patent; AMGEN INC.; WO2009/85185; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 4684-94-0 , The common heterocyclic compound, 4684-94-0, name is 6-Chloropicolinic acid, molecular formula is C6H4ClNO2, 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.

DMF (200 ml) was added to a 500 mL three-necked flask equipped with a thermometer, followed by the addition of m-trifluoromethylphenol.(0.26 mol, 42.2 g), potassium carbonate (0.266 mol, 37.2 g), 2-chloro-6-carboxypyridine (0.2 mol, 31.6 g) andCuprous chloride (1.0 g), warmed to 140 C, reacted for 8.0 h, cooled to room temperature, and poured into 600 ml of ice water.The pH of the brine was adjusted to 3, and the solid was precipitated, suction filtered, washed with water, and dried to give a white solid. Yield: 75%.

The synthetic route of 4684-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hebei University; Li Wan; Yang Zihui; Yang Fenglin; (6 pag.)CN108794390; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 38427-94-0, 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.38427-94-0, name is tert-Butyl pyridin-2-ylcarbamate, molecular formula is C10H14N2O2, molecular weight is 194.23, as common compound, the synthetic route is as follows.

(3-Formyl-pyridin-2-yl)-carbamic Acid tert-Butyl Ester (5-2) tert-Butyllithium (1.7 M, 14.5 mL, 24.6 mmol, 2.39 equiv) was added to a solution of pyridin-2-yl-carbamic acid tert-butyl ester (5-1, 2.00 g, 10.3 mmol, 1 equiv) in ethyl ether (100 mL) at -78 C., and the resulting mixture was warmed to 0 C. and stirred for 1 h. N,N-Dimethylformamide (8.00 mL, 103 mmol, 10.0 equiv) was added with rapid stirring. The mixture was stirred at 0 C. for 10 min, then partitioned between half-saturated aqueous ammonium chloride solution (100 mL). The aqueous layer was further extracted with ethyl acetate (100 mL), and the combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (40% ethyl acetate in hexanes) to afford (3-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (5-2) as a white solid. 1H NMR (300 MHz, CDCl3) delta 10.18 (br s, 1H), 9.91 (s, 1H), 8.64 (dd, 1H, J=4.9, 2.9 Hz), 7.98 (dd, 1H, J=7.6, 2.0 Hz), 7.12 (dd, 1H, J=7.6, 4.9 Hz), 1.55 (s, 9H); TLC (40% EtOAc/hexanes), Rf=0.41.

The chemical industry reduces the impact on the environment during synthesis 38427-94-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck & Co., Inc.; US6479512; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 915107-31-2, name is Methyl 6-chloro-5-methoxynicotinate. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Methyl 6-chloro-5-methoxynicotinate

Example 3. 3-Cyano-1-[6-(3,3-difluoro-pyrrolidin-1-yl)-5-methoxy-pyridin-3-ylmethyl]-1 H-pyrazole-4-carboxylic acid {l-amino-isoquinolin-6-ylmethyl)-amide {6-Chloro-S-methoxy-pyridin-3-yl)-methanol To a stirred solution of 6-chloro-5-methoxy-nicotinic acid methyl ester (0.5 g, 2.48 mmol) in anhydrous THF (20 mL) cooled to 0 C under nitrogen, was added UAIH4 (104 mg, 2.73 mmol). The reaction was allowed to warm to rt. The reaction was cooled to 0 C and quenched with water. Potassium sodium tartrate (Rochelle’s salt) was added and the mixture was filtered through Celite and washed with EtOAc (20 mL). The filtrate was separated and the aqueous extracted with EtOAc (20 mL). The combined organic layers were washed with brine (50 ml), dried over MgSO and the solvent removed in vacuo. The residue was purified by automated FC (EtOAc/petrol) to afford (6-chloro-5-methoxy-pyridin-3-yl)- methanol (710 mg, 82% yield) [MuEta]+ = 173.7

With the rapid development of chemical substances, we look forward to future research findings about 915107-31-2.

Reference:
Patent; KALVISTA PHARMACEUTICALS LIMITED; SMITH, Alun John; NOVAK, Andrew Richard; EVANS, David Michael; EDWARDS, Hannah Joy; STOCKS, Michael John; DAVIE, Rebecca Louise; MARSH, Sally Louise; HODGSON, Simon Teanby; (0 pag.)WO2016/83816; (2016); 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.1132-37-2, name is Dipyridin-2-ylmethane, molecular formula is C11H10N2, molecular weight is 170.2105, as common compound, the synthetic route is as follows.Computed Properties of C11H10N2

General procedure: In a dry flamed Schlenk tube under argon atmosphere, iridium dimers (1 eq.) and N^N ligands (2.2 eq.)were introduced in degassed 2:1 mixture of dichloromethane/methanol (8 mL). The reaction mixturewas stirred at 50 C for 6 h. After cooling down the solution to room temperature, excess of KPF6 (10eq.) was added affording a precipitate. The inorganic solid was filtered off and the filtrate wasevaporated. The solid was washed on a frit with diethyl ether (3×5 ml) and dried under vacuum to affordpure cationic iridium [Ir(C^N)2(N^N)][PF6] complexes.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1132-37-2, Dipyridin-2-ylmethane, and friends who are interested can also refer to it.

Reference:
Article; Sauvageot, Elodie; Lafite, Pierre; Duverger, Eric; Marion, Ronan; Hamel, Matthieu; Gaillard, Sylvain; Renaud, Jean-Luc; Daniellou, Richard; Journal of Organometallic Chemistry; vol. 808; (2016); p. 122 – 127;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 123853-39-4 ,Some common heterocyclic compound, 123853-39-4, molecular formula is C16H15Cl2NO4, 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.

Example 2 – Purification of 5-methoxycarbonyl-4-(2,3-dichlorophenyl)-2,6- dimethyl-1 ,4-dihydropyridine-3-carboxylic acid[0021] The crude carboxylic acid 2 from Example 1 (126g, 0.35 mol) was dissolved in a mixture of methanol (230ml_) and a solution of NaOH (34. Og, 0.85 mol) in water (230ml_). The solution was extracted with dichloromethane, and brine was added to the aqueous layer. The solids were collected by filtration and then re-suspended in water and stirred vigorously for 2h, after which the reaction mixture was cooled in an ice-water bath and phosphoric acid (85%, 21 ml_) was added. The solids were collected by filtration and washed with water. After drying under vacuum at 40C, compound 2 was suspended in a 1 : 1 mixture of acetone and heptane and vigorously stirred for 2h. The solids were collected by filtration and washed with heptane. Drying under high vacuum at 40C gave carboxylic acid 2 as a beige powder (95 g, 75% yield, 46%overall yield). Analysis by HPLC indicates a purity of 97.28%, with 0.13% of diacid 5 present.

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. 123853-39-4, 4-(2,3-Dichlorophenyl)-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALPHORA RESEARCH INC.; SOUZA, Fabio; PAN, Ming; WO2011/130852; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 71670-70-7, 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. 71670-70-7, name is 2-(Chloromethyl)-5-methylpyridine hydrochloride, molecular formula is C7H9Cl2N, 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.

A mixture of 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (Intermediate 17), (270 mg), 2-(chloromethyl)-5-methylpyridine hydrochloride (180 mg) and cesium carbonate (689 mg) in DMF (3 mL) was stirred at rt overnight. The crude product was purified by prep. LCMS then azeotroped with DCM to remove the residual AcOH to give the desired compound (141 mg). LCMS: m/z 399.20 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.04-1.67 (m, 4H) 1.79 (d, J=9.2 Hz, 2H) 1.97-2.21 (m, 2H) 2.32 (s, 3H) 3.56 (td, J=9.9, 4.5 Hz, 1H) 3.79-4.00 (m, 1H) 5.61-5.98 (m, 2H) 6.69 (d, J=8.0 Hz, 1H) 7.17 (d, J=5.1 Hz, 1H) 7.41 (d, J=7.7 Hz, 1H) 8.14 (s, 1H) 8.35 (d, J=5.1 Hz, 1H) 8.41 (s, 1H) 9.04 (d, J=6.5 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 71670-70-7, 2-(Chloromethyl)-5-methylpyridine hydrochloride.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; PAYNE, Andrew; CASTRO PINEIRO, Jose Luis; BIRCH, Louise Michelle; KHAN, Afzal; BRAUNTON, Alan James; KITULAGODA, James Edward; SOEJIMA, Motohiro; WO2015/49574; (2015); 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. 15862-50-7, name is 3-Bromo-2-methoxy-5-nitropyridine, molecular formula is C6H5BrN2O3, 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: 3-Bromo-2-methoxy-5-nitropyridine

Under 2 atmosphere, to a suspension of 3-bromo-2-methoxy-5- nitropyridine (5.00 g, 21.5 mmol, 1.00 equiv) and 5% Rh/C (0.123 g, 0.30 mol% Rh) in THF (107 mL, 0.200 M) hydrazine monohydrate (1.56 g, 25.8 mmol, 1.20 equiv) was added dropwise. The reaction mixture was monitored via TLC using EtOAc : hexanes 1:1 (v/v) as an eluent 15 until the disappearance of the starting 3-bromo-2-methoxy-5- nitropyridine (R/ = 0.90 (EtOAc : hexanes 1:1 (v/v)) and the appearance of the hydroxylamine intermediate (Rf = 0.61 (EtOAc : hexanes 1:1 (v/v)). Subsequently, sodium bicarbonate (2.14 g, 25.8 mmol, 1.20 equiv) was added to the reaction mixture followed by a solution of 20 methyl chloroformate (2.42 g, 25.75 mmol, 1.20 equiv) in THF (6.58 mL, 0.200 M) via a syringe pump (at a rate of 10.0 mL/h) . After the addition was complete, the reaction mixture was filtered through a short pad of celite and the celite was washed with EtOAc. The organic layers were combined and concentrated in vacuo. The residue was 25 purified by chromatography on silica gel, eluting with EtOAc : hexanes (3:7 to 1:1 (v/v)), to afford the title compound as a slightly light yellow solid (3.82 g, 13.8 mmol, 64% yield). Ri = 0.54 (EtOAc: hexanes 1:1 (v/v) ) . NMR Spectroscopy: XH NMR (500 MHz, (CD3)2SO, 25 C, delta) : 10.60 (s, 1H) 8.29 (d, J= 2.44 Hz, 1H) 8.13 (d, J = 2.44 Hz, 1H) 3.93 (s, 3H) 3.74 (s, 3H) . 13C NMR (125 MHz, (CD3)2SO, 25 C, delta) : 156.97, 155.40, 138.89, 135.74, 134. 47, 105.44, 5 55.01, 53.67. Mass Spectrometry: HRMS (ESI-TOF) (m/z) : calcd for C8Hi0BrN2O4 ([M + H]+), 276.9818, found, 276.9821.

With the rapid development of chemical substances, we look forward to future research findings about 15862-50-7.

Reference:
Patent; THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK; NGAI, Ming-Yu; HOJCZYK, Katarzyna, N.; (214 pag.)WO2016/57931; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 26163-03-1, 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. 26163-03-1, name is 3-Bromo-5-chloropyridin-2-amine. A new synthetic method of this compound is introduced below.

A mixture of 3-bromo-5-chloropyridin-2-amine (10 g, 49 mmol) and chloroacetaldehyde (50% in H2O, 12 mL, 98 mmol) in ethanol (100 mL) was heated at 50 C. overnight. It was then cooled to room temperature and concentrated. Acetone (30 mL) was added to the residue and the resulting mixture was stirred rapidly for 2 h. The resulting solid was collected through filtration and dried to afford 101a as a yellow solid (10.0 g, 89%). MS: [M+H]+231. 1H NMR (500 MHz, DMSO) delta 9.20 (s, 1H), 8.33 (s, 1H), 8.29 (s, 1H), 8.09 (s, 1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,26163-03-1, 3-Bromo-5-chloropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Young, Wendy B.; US2013/116262; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 60781-83-1, 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 60781-83-1, name is 4-Phenylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Compound chloroacetate (Chloroacetic acid) 8.88 g (93.9 mmol), dissolved in 17mL H2O and then triethylamine (Triethylamine) 17mL was added slowly and then the 2-amino-4-phenyl pyridine (2-Amino-4-phenylpyridine) 20 g ( put 117 mmol) was 5 hours at 90 . After cooling to room temperature, ethyl alcohol (Ethyl alcohol) into a 20mL 2 hours of reaction at 0 and filtered (Filter) 19.5 g to give the title compound 76-6 (73%).

According to the analysis of related databases, 60781-83-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hee Sung Material Co., Ltd; Kim, Ji Hee; Jang, So Hyun; Kim, Yeong Woo; Kim, Hyun Dong; Uhm, Song Jin; Lee, Ju Dong; (50 pag.)KR2016/1508; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem