Pyridine-derivatives

Synthetic Route of 393-55-5, Adding some certain compound to certain chemical reactions, such as: 393-55-5, name is 2-Fluoronicotinic acid,molecular formula is C6H4FNO2, 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 393-55-5.

Thionyl chloride (0.43 mL, 5.87 mmol) was added to a slurry of 2-fluoronicotinic acid (9, 0.69 g, 4.89 mmol) and N,N-dimethylformamide (0.1 mL, catalytic amount) in benzene (60 mL) at room temperature under nitrogen, after which the mixture was heated at reflux for 3 h. The solvent was removed under reduced pressure to provide an amber oil that was dissolved in 1,4-dioxane (40 mL) under nitrogen. The solution was treated with sodium borohydride (0.38 g, 10.0 mmol) and the mixture was stirred at room temperature for 24 h. The suspension was diluted with saturated NaHCO3 solution (200 mL) and extracted with diethyl ether (3×200 mL). The combined organic extracts were dried over Na2SO4, filtered and the solvents were removed under reduced pressure to provide the title compound: 1H NMR (300 MHz) 8.13 (d, J=3.7 Hz, 1H), 7.93-7.88 (m, 1H), 7.24-7.19 (m, 1H), 4.78 (s, 2H), 2.14 (bs, 1H) ppm.

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. 393-55-5, 2-Fluoronicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Coleman, Darrell Stephen; Jagdmann, Gunnar Erik; Johnson, Kirk Willis; Johnson, Michael Parvin; Large, Thomas Hallett; Monn, James Allen; Schoepp, Darryle Darwin; Barda, David Anthony; Britton, Thomas Charles; Dressman, Bruce Anthony; Henry, Steven Scott; Hornback, William Joseph; Tizzano, Joseph Patrick; Fichtner, Michael William; US2004/6114; (2004); 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. 33252-28-7, name is 6-Chloronicotinonitrile, the common compound, a new synthetic route is introduced below. name: 6-Chloronicotinonitrile

To a mixture of 6-chloropyridine-3-carbonitrile (10 g, 0.06 mol) and (2R)-2-methylpiperazine(6.35 g, 0.06 mol) in acetonitrile (80 mL), K2C03 (12.0 g, 0.09 mol) was added at RT. Theresulting mixture was stirred at 60C for 2 h (TLC indicated complete consumption ofstarting material). The reaction was brought toRT, quenched with water (150 mL) andextracted with EtOAc (3 x 80 mL). The combined organic extracts were dried over anhydrousNa2S04 and concentrated under reduced pressure. The residue was purified by columnchromatography (100-200 silica gel, 5% MeOH-DCM) to afford 6-[(3R)-3-methylpiperazine-1-yl]-pyridine-3-carbonitrile (10.0 g, 69% yield).

The synthetic route of 33252-28-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 623585-74-0 ,Some common heterocyclic compound, 623585-74-0, molecular formula is C7H5Cl2NO2, 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 3N methylmagnesium bromide solution in ether (5.6 ml) was added dropwise to a mixture of methyl 2,5- dichloroisonicotinate (2.90 g) , iron (III) acetylacetonate (0.25 g) , THF (85 ml) and N-methylpyrrolidone (8.5 ml) under ice-cooling, and this was stirred at the same temperature for 1 hour. After an aqueous saturated sodium chloride solution (100 ml) was added to the reaction mixture, this was extracted with ethyl acetate, and the ethyl acetate layer was washed with an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the desired product (1.82 g) as an oil.1H-NMR (CDCl3) delta 2.52 (3H, s) , 3.99 (3H, s), 7.74 (IH, s) ,8.34 (IH, s) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,623585-74-0, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2006/64944; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 85148-95-4, 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. 85148-95-4, name is 6-Formylpicolinonitrile, molecular formula is C7H4N2O, 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.

(1) 2,6-Dimethyl-4-(6-cyano-2-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-beta-chloroethyl ester 5-methyl ester 6-Cyano-2-pyridine aldehyde (1.613 g, 12.2 mmol), chloroethyl acetoacetate (2.009 g, 12.2 mmol) and methyl 3-aminocrotonate (1.364 g, 12.2 mmol) were dissolved in 16 ml of isopropanol, and the solution was stirred at 35° to 40° C. under a nitrogen gas stream for 14 hours. The reaction solvent was distilled off under reduced pressure, and the residue was purified by column chromatography [silica gel; ethyl acetate-n-hexane (5:6)]. The crude product thus obtained was recrystallized from isopropyl ether-methanol to obtain 1.546 g (34percent yield) of the above-captioned compound. IR numaxKBr cm-1: 2225(CN), 1695(C=O); 1680(C=O) STR7

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 85148-95-4, 6-Formylpicolinonitrile.

Reference:
Patent; The Green Cross Corporation; US4849429; (1989); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 851386-40-8, Adding some certain compound to certain chemical reactions, such as: 851386-40-8, name is 4-Chloro-2,5-difluoropyridine,molecular formula is C5H2ClF2N, 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 851386-40-8.

[(00592] Step 1 : Preparation of (4-chloro-2,5-difluoropyridin-3-yl)(5-cyclopropylisoxazol-3-yl)methanone . A cold (-78 C) solution of 4-chloro-2,5-difluoropyridine (246 mg, 1.65 mmol) in THF (15.0 mL) was treated with 2.5 M n-BuLi in hexanes (718 pL, 1.79 mmol). After stirring for 2 h at -78 C, the reaction mixture was treated with a solution of methyl 5- cyclopropylisoxazole-3-carboxylate (250 mg, 1.50 mmol) in THF (2 mL). The resulting mixture was stirred overnight at ambient temperature before quenching with saturated NH4Q(aq). Subsequently, the mixture was diluted with water, and extracted with EtOAc. The organic extracts were washed with brine, dried over anhydrous Na2S04(S>, filtered, and concentrated in vacuo. The crude residue was purified by silica chromatography (10-90% EtOAc in hexanes) to afford the title compound (201 mg, 47%).

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. 851386-40-8, 4-Chloro-2,5-difluoropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; WALLS, Shane M.; REN, Li; RAMANN, Ginelle A.; MORENO, David A.; METCALF, Andrew T.; MCFADDIN, Elizabeth A.; KOLAKOWSKI, Gabrielle R.; BLAKE, James F.; DAI, Donghua; HAAS, Julia; JIANG, Yutong; KAHN, Dean; (368 pag.)WO2019/143994; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 847729-27-5 ,Some common heterocyclic compound, 847729-27-5, molecular formula is C7H5ClFNO2, 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 2. Methyl 5-fluoro-2-methvlnicotinate; A mixture of methyl 2-chloro-5-fluoronicotinate (step 1, 1.5 g, 7.91 mmol), tetrakis (triphenylphoshine)palladium (914 mg, 0.79 mmol), methyboronic acid (521 mg, 8.70 mmol) and potassium carbonate (3.28 g, 23.7 mmol) in 1,4-dioxane (20 ml) was heated at 110 C for 20 h under nitrogen atmosphere. The reaction mixture was filtered through a pad of celite (Celite(trademark) (diatomaceous earth) ) and the filtrate was concentrated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (20/1 to 4/1) to afford 936 mg (64%) of the title compound: ¹H-NMR (CDCl3) No. 8.49 (1 H, d, J = 3.0 Hz), 7.93 (1 H, dd, J = 3.0, 8.7 Hz), 3.94 (3H, s), 2.81 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,847729-27-5, its application will become more common.

Reference:
Patent; PFIZER JAPAN INC.; PFIZER INC.; WO2005/105732; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1151989-04-6 ,Some common heterocyclic compound, 1151989-04-6, molecular formula is C19H14N2O5S2, 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 Compound 11:Aleclon hemifumarate (121 mg, 0.22 mmol, 1 eq) at room temperature in the darkDissolved in dry dimethylformamide (4 mL),Triethylamine (34 mg, 46 muL, 0.33 mmol, 1.5 eq) was added slowlyStir for half an hour,Compound 8 (95 mg, 0.23 mmol, 1.05 eq) and then slowly addedTrace of 4-dimethylaminopyridine in dimethylformamide(2mL) solution,The mixture was stirred at room temperature under an argon atmosphere overnight. The solvent is removed under reduced pressure and subjected to rapid preparative column chromatography.One-step purification (methanol: methylene chloride, 1/50 to 1/10 v/v) afforded white solid (yield: 67 mg, 37%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1151989-04-6, its application will become more common.

Reference:
Patent; Fudan University; Sun Tao; Jiang Chen; (22 pag.)CN109846824; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 914358-72-8, Adding some certain compound to certain chemical reactions, such as: 914358-72-8, name is 5-Bromo-3-chloro-2-methylpyridine,molecular formula is C6H5BrClN, 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 914358-72-8.

A suspension of 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi( 1,3,2-dioxaborolane) (0.836 g, 3.29 mmol), 5-bromo-3-chloro-2-methylpyridine (0.34 g, 1.65 mmol), potassium acetate (0.485 g, 4.94 mmol) in dioxane (5 mL) was degassed with a stream of argon for a couple of minutes. 1,1?-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.067 g, 0.08 mmol) was added and the mixture was heated at reflux under N2 for 1.5 h. The mixture was allowed to cool and filtered. The filter cake was washed with EtOAc. The filtrate was concentrated in vacuo and column chromatography using EtOAc 0% to 80% in heptane gave 442 mg (100%) of the title compound. 1H NMR (500 MHz, CDC13) delta ppm1.35 (s, 12 H), 2.65 (s, 3 H), 7.95 -8.03 (m, 1 H), 8.69 (d, 1 H); MS (ES+) mlz: 172 [M+C6H9]+

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. 914358-72-8, 5-Bromo-3-chloro-2-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; MINIDIS, Anna; RAHM, Fredrik; VIKLUND, Jenny; WO2013/54108; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 103058-87-3, 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. 103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde, molecular formula is C7H6BrNO2, 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) 5-Bromo-2-methoxv-3- (4-methoxv-but-1 (E, Z)-envl)-pyridine; 2.45 mi of a 1 M solution of sodium-bis (trimethylsilyl) amide in tetrahydrofuran are added. to a suspension of 2.4 mmol (3-methoxy-propyl)-triphenyl-phosphonium bromide [111088-69-8] in 8 ml tetrahydrofuran unter an argon atmosphere at 0C. The reaction mixture is stirred for 30 minutes at 0C and then 1.6 mmol 5-bromo-2-methoxy-pyridine-3-carbaldehyde [103058-87- 3] are added. The reaction mixture is warmed to room temperature and then diluted with tert- butyl methyl ether. The solution is washed with saturated aqueous sodium hydrogen- carbonate solution. The organic layer is dried over sodium sulphate, filtered and concentrated. The title compound is obtained from the residue by means of flash chromatography (Si02 60F) and identified based on its Rf value.

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 103058-87-3, 5-Bromo-2-methoxynicotinaldehyde.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90305; (2005); 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.1220910-89-3, name is Benzyl (3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbamate, molecular formula is C21H17FN6O2, molecular weight is 404.4, as common compound, the synthetic route is as follows.Recommanded Product: Benzyl (3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbamate

A 5-L, three-neck, round-bottom flask was equipped with an overhead stirrer, a thermocouple, a 500-mL addition funnel and a nitrogen-inlet adapter. The flask was dried with a heat gun under a flow of nitrogen to an internal temperature of 60C. The flask was charged with intermediate 7 (110.0 g, 0.272 mol, AMRI lot No. DUG-AF-202Q)) and anhydrous THF (2.2 L, 20 vol). The slurry was stirred and a light green solution formed. The addition funnel was charged with 1.0 M lithium hexamethyldisilazide (299 mL, 0.286 mol, 1.05 eq.). The LiHMDS solution was added dropwise to the solution of intermediate 7 over approximately 25 minutes. A red solution formed. The solution was stirred one hour at room temperature and then DMPU (34.9 g, 0.272 mol, 1 eq) was added, and the mixture turned to a yellow slurry. The batch was cooled in an ice bath to 5.7C. R-(-)-Glycidyl butyrate (41.25 g, 0.286 mol, 1.05 eq) was then added in one portion. The mixture was stirred in the ice bath for 0.5 hour and then was warmed to room temperature and stirred overnight. The reaction formed a tan slurry at this point, and HPLC analysis after 15 hours indicated that there was approximately 87% TR-700, 1.6% intermediate 7, and approximately 7% of the butyrate ester of TR-700. A small amount of sodium methoxide in methanol (11 mL, 0.1 vol) was added, and the batch was stirred for 1 hour to remove the residual ester. The in-process HPLC analysis at this point showed there was approximately 90.7% TR-700 and 0.2% of the butyrate ester. The reaction was quenched by the addition of 10% w/w ammonium chloride solution (1.1 L, 10 vol). A modest exothermic event from 22C to 25C was observed upon addition of the ammonium chloride solution. The two-phase mixture was distilled to a pot temperature of 700C (atmospheric pressure) to remove approximately 2.2 L of the THF. This formed a thick slurry which is diluted with water (550 mL, 5 volumes). The slurry was cooled to room temperature (23.6C) and was filtered. The filter cake was washed with water (1.1 L, 10 vol) and methanol (550 mL, 5 vol) to give TR-700 as a white solid. The wet cake was dried overnight in a vacuum oven at 500C to give 89.7 g of TR-700 (89% yield) that was 97.8% (AUC) by HPLC analysis. The TR-700 was further purified by reslurrying in 2.7 L (30 vol) of 4: 1 methanol/water at 700C, cooling to 230C, filtering and washing with methanol (180 ml). This removed some of the over-alkylated product that is observed. The purified TR- 700 was recovered in 96% yield (85% overall yield), and the purity was improved to 98.4% (AUC) by HPLC analysis. The palladium content was 10 ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1220910-89-3, Benzyl (3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; TRIUS THERAPEUTICS; COSTELLO, Carrie, A.; SIMSON, Jaqueline, A.; DUGUID, Robert, J.; PHILLIPSON, Douglas; WO2010/42887; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem