Day: April 14, 2022

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

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 13958-93-5, name is 3,5-Dichloroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3,5-Dichloroisonicotinic acid

Step A N-(BOC)-4-((3′,5′-dichloroisonicotinoyl)amino)-(L)-phenylalanine, methyl ester A slurry of 3,5-dichloroisonicotinic acid (3.1 g, 16.11 mmol) in 10 mL of CH2Cl2 was treated with DMF (50 muL) and thionyl chloride (1.23 mL, 16.91 mmol) and heated to reflux for 5 h. The reaction was concentrated to give a yellow oil. This oil was dissolved in 5 mL of CH2Cl2 and added to N-(BOC)-4-amino-(L)-phenylalanine, methyl ester (4.00 g, 14.39 mmol) and 4-methylmorpholine (2.7 mL, 24.21 mmol) in 25 mL of CH2Cl2 at 0 C. After stirring for 2 h at this temperature, the reaction was quenched with water (50 mL) and extracted into CH2Cl2 (3*100 mL). The combined organics were combined, dried over anhydrous MgSO4 and concentrated in vacuo to give a yellow solid. Trituration with CH2Cl2 gave 5.5 g of a while solid 1H NMR (500 MHz, CDCl3): delta 8.63 (s, 2H); 7.58 (d, J=8.2 Hz, 2H); 7.23 (d, J=8.2 Hz, 2H); 6.91 (d, J=8.4 Hz, 1H); 4.39 (m, 1H); 3.70 (s, 3H); 3.11 (m, 1H); 2.91 (m, 1H); 2.00 (s, 9H); MS m/e 468.20 (M+).

With the rapid development of chemical substances, we look forward to future research findings about 13958-93-5.

Reference:
Patent; Lin, Linus S.; Doherty, George; Shah, Shrenik K.; Chang, Linda L.; Hagmann, William K.; Mumford, Richard A.; US2003/8861; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 67058-77-9 ,Some common heterocyclic compound, 67058-77-9, molecular formula is C7H5N3O2, 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 3-nitro-1H-pyrrolo[2,3-c]pyridine (250 mg, 1.53 mmol) in DMF (5 mL) was added NaH (60% dispersion in mineral oil, 61 mg, 1.53 mmol). After stirred at 0 C for 10 mi dimethylsulfate (193 mg, 1.53 mmol) was added dropwise. After stirred at 0 C for 3 hrs, the mixture was partitioned in a mixture of ethyl acetate (50 mL) and H20 (50 mL) and the aqueous phase was extracted by ethyl acetate (50 mL x 2). Organic phase was combined, dried over anhydrous Na2SO4, and evaporated in vacuum. The residue was purified by flash column (ACN in water: 5% to 50%) to afford 1-methyl-3-nitro-1H-pyrrolo[2,3-c]pyridine (30 mg, 11%) as a white solid. ?H NIVIR (400 IVIHz, CD3OD): oe = 8.94 (d, J = 0.8 Hz, 1H), 8.61 (s, 1H), 8.43 (d, J = 5.6 Hz, 1H), 8.12 (dd, J= 5.2, 0.8 Hz, 1H), 4.06 (s, 3H). MS: m/z 178.0 (M+H).

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. 67058-77-9, 3-Nitro-1H-pyrrolo[2,3-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below., Safety of 5-(Trifluoromethyl)pyridin-3-amine

[00262] 5-(Trifluoromethyl)pyridin-3-amine (686 mg, 4.23 mmol) was dissolved in anhydrous DMF (24 rnL) and sodium hydride (231 mg, 5.77 mmol – 60% in mineral oil) added over 3 minutes before stirring the mixture at 200C under a nitrogen atmosphere for 20 minutes. 3-Bromo-8-bromo/chloroimidazo[l,2-a]pyrazine (895 mg, 3.85 mmol) was then added over 5 minutes and the mixture stirred at 200C under a nitrogen atmosphere for 16 hours. Water (170 mL) was added to the reaction mixture and the resulting precipitate was washed with water (125 mL) and then 40-60 petroleum ether (85 mL) to give 3-bromo-N-(5- (trifluoromethyl)pyridin-3-yl)imidazo[l,2-a]pyrazin-8-amine (871 mg, 63%) as an off-white solid. LCMS RT = 2.36 min, MH+ 359.9. 1U NMR (d6-DMSO): 9.42 (IH, s), 8.82 (IH, s), 8.62 (IH, d, J5.2), 8.01 (IH, d, J4.7), 7.89 (IH, s), 7.73 (IH, d, J4.8), 7.44 (IH, dd, J5.1, 0.9).

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, 112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine.

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; PRICE, Paul Damien; MIDDLETON, Penny; WO2010/69684; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17075-15-9, 4-(Methylsulfonyl)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, SDS of cas: 17075-15-9, blongs to pyridine-derivatives compound. SDS of cas: 17075-15-9

EXAMPLE 2A 4-[2-[4-(1,1-dimethylethoxy)phenyl]ethoxy]pyridine (Compound 9A) To a suspension of about one-half gram of 60% NaH (dispersion in oil) in 10 mL of dry DMF was added 1.5 g (0.0077 m) of 2-[4-(1,1-dimethylethoxy)phenyl]ethanol. The mixture was stirred in a warm water bath until hydrogen evolution ceased. After 30-40 minutes, 1 g (0.0064 m) of 4-(methylsulfonyl)pyridine in 5-7 mL of DMF was added. The mixture was stirred at room temperature overnight, then diluted with water. The product was extracted into CH2 Cl2, and the extracts were washed with saturated brine, filtered through phase separating paper, and concentrated in vacuo. The resulting material was azeotroped with xylene to remove excess DMF. This material was adsorbed onto silica gel and chromatographed over silica gel 60 (230-400 mesh) using CH2 Cl2 ?50% EtOAc/CH2 Cl2 to give the title product as an oil. Yield 0.7 g.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17075-15-9, 4-(Methylsulfonyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; DowElanco; US5399564; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem