Month: April 2022

Application of 79491-46-6, 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. 79491-46-6, name is 2,6-Dibromo-3-methoxy-5-nitropyridine, molecular formula is C6H4Br2N2O3, 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.

5.43 3-Methoxy-5-nitropyridine-2,6-diamine (33) A solution of 32 (0.5 g, 1.6 mmol) in aqueous ammonia (15 M, 12 mL, 180 mmol) was heated at 90 C for 1 h in a microwave oven. The reaction mixture was cooled, the yellow solid was collected by filtration, washed with a small amount of water, and dried under vacuum to afford 33 (230 mg, 78%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6, 393 K) delta = 7.48 (s, 1H), 7.35 (br, 2H), 6.81 (br, 2H), 3.80 (s, 3H); MS ES+ve m/z 185 (M+H)+.

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 79491-46-6, 2,6-Dibromo-3-methoxy-5-nitropyridine.

Reference:
Article; Miah, Afjal H.; Abas, Hossay; Begg, Malcolm; Marsh, Benjamin J.; O’Flynn, Daniel E.; Ford, Alison J.; Percy, Jonathan M.; Procopiou, Panayiotis A.; Richards, Steve A.; Rumley, Sally-Anne; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 4298 – 4311;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 33252-28-7, Adding some certain compound to certain chemical reactions, such as: 33252-28-7, name is 6-Chloronicotinonitrile,molecular formula is C6H3ClN2, 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 33252-28-7.

Example 29Step A6-Bromonicotinonitrile. 6-Chloronicotinonitrile (13.8 g, 100 mmol) was heated at 145 C in phosphorus tribromide (150 ml.) for 32 h. After cooling, the mixture was concentrated in vacuo. To the residue was added phosphorus tribromide (150 ml_), and the mixture was heated at 145 C for another 32 h. After cooling, the mixture was concentrated in vacuo, and an ice-water mixture (500 ml.) was added. Sodium bicarbonate was added to neutralize the mixture, and the product was extracted with ethyl acetate (3 chi 250 ml_). The combined organic extracts were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo, and the residue was chromatographed (hexanes-ethyl acetate) to give 14.9 g (81 %) of 6-bromonicotinonitrile as a white solid: 1 H NMR (400 MHz, CDCI3) S 7.66 (d, J = 1 1.0 Hz, 1 H), 7.80 (dd, J = 3.1 , 1 1.0 Hz, 1 H), 8.67 (d, J = 3.1 Hz, 1 H); MS (M+H)+ m/z=183.0, 185.0.

According to the analysis of related databases, 33252-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; BURGESS, Gary; WO2012/114223; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1256789-09-9, Adding some certain compound to certain chemical reactions, such as: 1256789-09-9, name is Methyl 6-chloro-2,4-dimethylnicotinate,molecular formula is C9H10ClNO2, 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 1256789-09-9.

a) Synthesis of 2-(methoxymethyl)-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid methylesterTo a solution of 710 mg, (3.6 mmol) 6-chloro-2,4-dimethyl-pyridine-3-carboxylic acid methylester in CCI4 (16 ml) were added 688 mg (3.90 mmol) N-bromosuccinimide, 59 mg (0.36 mmol) AIBN and 210 muIota (3.72 mmol) acetic acid . The reaction mixture was irradiated with a 200W Wolfram lamp at 60 C for 24 h. The mixture was then filtered through celite, washed with CCI4 and concentrated in vacuo. After CC (hexane/EtOAc 97:3) of the residue a mixture of 6-chloro-2,4-dimethyl-pyridine-3-carboxylic acid methylester, 4-(bromomethyl)-6- chloro-2-methyl-pyridine-3-carboxylic acid methylester and 2-(bromomethyl)-6-chloro-4- methyl-pyridine-3-carboxylic acid methylester was obtained. This mixture was dissolved in dioxane (10 ml) and added at 0 C to a solution prepared by dissolving 594 mg (25.8 mmol) sodium in MeOH (11 ml) at 0 C. This reaction mixture was stirred at RT for 3 h. Then the reaction solution was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. After CC (hexane/EtOAc 97:3) of the residue again a mixture of 6-chloro-4-(methoxymethyl)-2-methyl- pyridine-3-carboxylic acid methylester and 6-chloro-2-(methoxymethyl)-4-methyl-pyridine-3- carboxylic acid methylester was obtained. This material was dissolved in NMP (7.8 ml) and 860 muIota (9.85 mmol) morpholine and 1.36 g (9.85 mmol) K2C03 were added followed by heating at 100 C for 5 h. Then the mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 9:1) provided 90 mg (0.32 mmol, 9%) 2-(methoxymethyl)-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid methylester.

According to the analysis of related databases, 1256789-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; KUeHNERT, Sven; BAHRENBERG, Gregor; KLESS, Achim; SCHROeDER, Wolfgang; LUCAS, Simon; WO2012/52167; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 693286-31-6, Adding some certain compound to certain chemical reactions, such as: 693286-31-6, name is 4,6-Dichloro-2-methylnicotinic acid,molecular formula is C7H5Cl2NO2, 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 693286-31-6.

To a solution of 4, 6-dichloro-2-methyl-nicotinic acid (8. 5 g, 41.3 mmol) in anhydrous tetrahydrofuran (85 mL), 1,3-dicyclohexyl-carbodiimide (9.27 g, 44.9 mmol), 4- (DIMETHYLAMINO)-PYRIDINE (140 mg, 1.14 mmol), and cyclopentanol (5.1 mL, 4. 83 g, 56.2 mmol) are added in succession. The mixture is stirred for 15 minutes at room temperature and brought to reflux at which it is maintained for 1 hour. The reaction is cooled to ambient temperature and all volatiles are removed in vacuo. The residue is dissolved in a mixture of ethyl acetate and hexane (1: 12,200 mL) and the resultant suspension is filtered over a small pad of silica gel (45 g), which is subsequently rinsed with additional 200 mL of the same mixture of hexane and ethyl acetate. The obtained solution is concentrated in vacuo and the residue chromatographed on silica gel (hexane: ethyl acetate 15: 1) to afford 4, 6-dichloro-2- methyl-nicotinic acid cyclopentane ester as colorless oil.

According to the analysis of related databases, 693286-31-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROGEN CORPORATION; WO2004/43925; (2004); 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.39774-26-0, name is 2-Bromo-6-phenylpyridine, molecular formula is C11H8BrN, molecular weight is 234.09, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Bromo-6-phenylpyridine

To a solution of 21-1 (2.70 g, mixture from previous step) in tetrahydrofuran (50 mL) cooled to -78 C. under nitrogen, n-butyllithium (2.5 M in hexanes, 5.8 mL, 14.5 mmol) was added dropwise. The mixture was stirred for 45 minutes then N,N-dimethylformamide (1.80 mL, 23 mmol) was added. The mixture was stirred at -78 C. for 1 hour, warmed to room temperature, quenched with water, and extracted with ethyl acetate. The organic layer was washed three times with water, once with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography, eluting with 2.5% followed by 5% ethyl acetate in hexanes to give 6-phenylpicolinaldehyde (21-2, 1.24 g) as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39774-26-0, 2-Bromo-6-phenylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Hardy, Lindsay Bonner; Boyd, Vincent A.; Market, Robert V.; Thrash, Thomas P.; Young, Brandon M.; (83 pag.)US2018/312523; (2018); 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, 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. Computed Properties of C6H5F3N2

The compound of Example 36A(1 g, 6.2 mmol), trifluoroacetic anhydride (1.30 g, 6.2 mmol) and pyridine(0. 54 g, 6.8 mol) are dissolved in tetrahydrofuran (20ml) under an argon atmosphere. The solution is cooled to-78 C with stirring and lithium diisopropylamide (3.0 ml of a 2 M solution in THF/heptane, 6.0 mmol) is added dropwise. The reaction mixture is allowed to warm to room temperature, and then stirred at room temperature overnight. The reaction is quenched with water and extracted with ethyl acetate (3 x 100 ml). The ethyl acetate phase is washed with brine, dried with magnesium sulphate monohydrate, filtered and concentrated to give a yellow oil. The oil is purified by flash chromatography on silica gel with cyclohexane/ethyl acetate mixtures as eluent. Yield: 1.05 g (66%of th.) HPLC (method 8): Rt = 4.23 min MS(EI) :m/z = 259(M+H)”IHh R (300 MHz, DMSO-d6) :8 = 8. 46 (s, 1H) ; 8.84 (s, 1H) ; 9.10 (s, 1H) ;11. 80 (s,1H) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 112110-07-3.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/20412; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 33252-28-7, Adding some certain compound to certain chemical reactions, such as: 33252-28-7, name is 6-Chloronicotinonitrile,molecular formula is C6H3ClN2, 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 33252-28-7.

Triethylamine (4.13 g, 3 niL, 40.8 mmol, 4 eq) is added to a solution of 6-chloro- nicotinonitrile (1.38 g, 10 mmol, leq), (S)-2-methyl- piperazine (1.0Og, 10 mmol, leq) in DMF (15 niL), and the resulting solution is stirred at rt for 14 h. A white precipitate of triethylamine hydrochloride forms in the course of the reaction. Water (15 mL) and EtOAc (100 mL) are added, the organic layer is separated, dried over sodium sulfate and concentrated under reduced pressure to a white residue. The solid is further dried under high vacuum to yield the desired product as a white solid (1.4 g, 69%). 1H NMR (400 MHz, CHLOROFORM-cf) delta ppm 8.38 (s, 1 H), 7.58 (d, J=9.60 Hz, 1 H), 6.59 (d, J=9.09 Hz, 1 H), 4.19 – 4.31 (m, 2 H), 3.08 – 3.15 (m, 1 H), 2.92 – 3.04 (m, 1 H), 2.81 – 2.91 (m, 2 H), 2.57 – 2.65 (m, 1 H), 1.15 (d. J=6.32 Hz, 3 H).

According to the analysis of related databases, 33252-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 16727-47-2, 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.16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, molecular formula is C19H16BrNO2, molecular weight is 370.2398, as common compound, the synthetic route is as follows.

To the stirred solution of (2,6-dibenzyloxy-3-bromo-pyridine) 43-1 (5 g, 13.50 mmol)in dry THF (30 mL), 2.5 M BuLi in Hexane (7.08 g, 20.26 mmol) was added at -78C under inertatmosphere and stirred for 1 hour at rt. After that, dry DMF (1.5 mL) was added to the reactionmixture dropwise at -78C and stirring was continued for further 2 hours at room temperature. After completion of reaction, as evidenced from TLC, reaction mixture was quenched withsaturated ammonium chloride solution. The aqueous phase was extracted with ethyl acetate.Combined organic layer was separated, dried over anhydrous sodium sulfate and concentratedunder vacuum. The crude reaction mass was purified by column chromatography to obtain5 desired compound 43-2 (2,6-dibenzyloxypyridine-3-carbaldehyde) (2.8 g, 8.77 mmol, 64.92%yield) as sticky solid. ES (M+H): 320.

Statistics shows that 16727-47-2 is playing an increasingly important role. we look forward to future research findings about 2,6-Bis(benzyloxy)-3-bromopyridine.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Christoper, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; DUPLESSIS, Martin; CHEN, Chi-Li; (791 pag.)WO2018/237026; (2018); A1;,
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. 639091-75-1, name is Methyl 2-(Boc-amino)isonicotinate, the common compound, a new synthetic route is introduced below. Safety of Methyl 2-(Boc-amino)isonicotinate

Step 1. Preparation of methyl 2-[(tert-butoxycarbonyl(methyl)amino]isonicotinate A slurry of methyl 2-[(tert-butoxycarbonyl)amino]isonicotinate (5.0 g, 2.0E1 mmol) in DMF (75 mL) was cooled to ?0 C. (ice/NaCl) and treated with a 1.0 M solution of sodium hexamethyldisilazane in THF (24 mL, 24 mmol) dropwise over 25 min to afford a clear, yellow/brown solution. The reaction mixture was stirred for 30 min at 0 OC and treated with methyl iodide (1.4 mL, 22 mmol). The reaction mixture was stirred for 20 min, the cold bath was removed, and the reaction mixture stirred at rt for 2 h; HPLC/LC MS indicated complete conversion to product. The reaction mixture was cooled to ?0 C. and the reaction was quenched by the addition of saturated aqueous NH4Cl (25 mL). The mixture was allowed to warm to rt and was extracted with Et2O (3*50 mL). The combined organics were washed with saturated aqueous NaHCO3 (1*50 mL) and 10% aqueous LiCl (2*50 mL), dried (Na2SO4), and concentrated in vacuo to afford a bright yellow oil with precipitate. The crude material was further dried on high vacuum overnight to afford the crude title compound as a light colored solid/yellow oil (5.29 g). MS (ESI+) for C13H18N2O4LC m/z 267.1 (M+H)+; HPLC retention time: 3.78 min (Method B).

The synthetic route of 639091-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXITHERA PHARMACEUTICALS INC.; Chrusciel, Robert A.; Gadwood, Robert C.; Hayward, Neil J.; Melnick, Michael J.; Navia, Manuel A.; Poel, Toni J.; Stassen, Frans L.; Stewart, Catherine A.; US2015/225389; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 823-39-2, 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. 823-39-2, name is 3,4-Dimethylpyridin-2-amine. A new synthetic method of this compound is introduced below.

G. (L)-N-Boc-6-methanesulfonylnorleucine allyl ester (11b) As an alternative approach, to a cooled (0 C. bath) solution of (L)-N-Boc-6-hydroxynorleucine allyl ester (10) from E above (80 mg, 0.28 mmol), triethyl amine (80 muL, 0.57 mmol), dimethyl amino pyridine (DMAP) (cat) in anhydrous CH2 Cl2 (1 mL) under N2 was added methane sulfonyl chloride (27 muL, 0.34 mmol). The contents were warmed (rt) and the mixture was concentrated under reduced pressure and purified by flash chromatography (silica gel; EtOAc/hexane, (1:19, v/v)) to provide a light yellow oil identified as (L)-N-Boc-6-methanesulfonylnorleucine allyl ester (11 b) (81 mg, 79%): TLC (SiO2, EtOAc/hexane (1:1, v/v)) Rf =0.36; 1 H NMR (360 MHz, CDCl3) delta5.98-5.84 (m, 1 H), 5.38-5.24 (m, 2 H), 5.08-4.96 (m, 1 H), 4.70-4.58 (m, 2 H), 4.38-4.26 (m, 1 H), 4.21 (t, J=6.4 Hz, 2 H), 2.99 (s, 3 H), 1.95-1.35 (m, 15 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,823-39-2, its application will become more common.

Reference:
Patent; Keystone Biomedical, Inc.; US5952492; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem