Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 1721-23-9, 3-Cyano-2-methylpyridine, 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: 1721-23-9, blongs to pyridine-derivatives compound. SDS of cas: 1721-23-9

1-Amino-3(2-methyl-3-pyridyl)2,5-naphthyridine To 5.9 of 3-cyano-2-methylpyridine dissolved in 30 ml. of dimethylformamide, gradually add 6.7 g. of potassium t-butoxide at about 5 C. Maintain the mixture at 5 C for 4-6 hours and quench the reaction in ice water. Collect the crystalline precipitate and recrystallize from toluene to yield 1-amino-3(2-methyl-3-pyridyl)-2,5-naphthyridine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1721-23-9, 3-Cyano-2-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Schering Corporation; US4017500; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, Formula: C6H8BrN3, blongs to pyridine-derivatives compound. Formula: C6H8BrN3

Step 3. 5-bromo-N3-isopropyl-N2-methylpyridine-2.3-diamine and 6-bromo-2,2,3-trimethyl-2.3-dihydro- 1H-imidazor4.5-blpyridine; 5-bromo-N2-methylpyridine-2,3-diamine (54.4 mg, 0.269 mmol) was dissolved in isopropyl acetate (1.5 ml) and acetone (23 mul, 0.31 mmol), trifluoroacetic acid (0.045 ml, 0.58 mmol), and sodium triacetoxyborohydride (64 mg, 0.30 mmol) were added. The reaction was stirred under nitrogen at room temperature for 4 hours, and then more acetone was added (0.040 ml) along with TFA (0.090 ml) and isopropyl acetate (0.5 ml). The reaction was then stirred overnight. This reaction was repeated on a larger scale using 5-bromo-N2-methylpyridine-2,3-diamine (288 mg, 1.43 mmol), 2,2,2-trifluoroacetic acid (0.30 ml, 3.9 mmol), acetone (0.13 ml, 1.8 mmol), and sodium triacetoxyborohydride (352 mg, 1.66 mmol). Then, both reactions were poured into water (25 ml), and solid sodium hydroxide was added to raise the pH to about 10. The layers were separated, and the aqueous phase was extracted with EtOAc. The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and dried under high vacuum. To afford 5-bromo-N3-isopropyl-N2-methylpyridine-2,3-diamine and 6-bromo-2,2,3- trimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridine (399 mg, 97% combined yield). 5-bromo-N3-isopropyl-N2-methylpyridine-2,3-diamine: MS (ESI pos. ion) m/z: 244 (MH+, 79Br), 246 (MH+, 81Br). Calculated exact mass for C9H14BrN3 243 (79Br), 245 (81Br). 6-bromo-2,2,3-trimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridine: MS (ESI pos. ion) m/z: 242 (MH+, 79Br), 244 (MH+, 81Br). Calculated exact mass for C9H12BrN3 241 (79Br), 243 (81Br).

The synthetic route of 89415-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/17822; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 178876-83-0, Methyl 6-amino-3-bromopicolinate, 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, Computed Properties of C7H7BrN2O2, blongs to pyridine-derivatives compound. Computed Properties of C7H7BrN2O2

Example 57D methyl 3-bromo-6-fluoropicolinate To a solution of nitrosonium terafluoroborate (17.8 g) in dichloromethane (100 mL) at 5 C. was added EXAMPLE 57C (26.1 g) in dichloromethane (250 mL) over 1 hour. The reaction mixture was stirred an additional 30 minutes at 5 C., and allowed to warm to room temperature overnight. The reaction mixture was quenched with pH 7 buffer (100 mL), and neutralized with solid potassium carbonate. The resulting mixture was extracted with ether (twice), and the combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was chromatographed on silica gel using 1-10% ethyl acetate in hexanes to provide the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,178876-83-0, Methyl 6-amino-3-bromopicolinate, and friends who are interested can also refer to it.

Reference:
Patent; AbbVie Inc.; WANG, LE; Doherty, George; Wang, Xilu; Tao, Zhi-Fu; Bruncko, Milan; Kunzer, Aaron R.; Wendt, Michael D.; Song, Xiaohong; Frey, Robin; Hansen, Todd M.; Sullivan, Gerard M.; Judd, Andrew; Souers, Andrew; US2013/96120; (2013); A1;,
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 1052714-48-3, name is 6-Bromo-3-fluoropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-Bromo-3-fluoropicolinic acid

6-Bromo-3-fluoro-2-methylpyridine (5 g, 26.3 mmol) was dissolved in 100 ml of water and potassium permanganate (12.5 g, 78.9 mmol) was added. The reaction mixture was heated to reflux for 12 h. Solid constituents were removed by filtration. The filter cake was washed three times with 100 ml of water. The collected wash solutions were concentrated and the crude product was obtained as white solid, which was further reacted directly. The crude product (6 g) was dissolved in 20 ml of dimethylformamide and, after adding sodium ethanethiolate (6.6 g, 78.9 mmol), the mixture was stirred for 12 h at room temperature. The reaction mixture was filtered and the organic phase was concentrated. The residue was purified by chromatography (mobile phase: water/acetonitrile) and the product was obtained in the form of a yellow solid. log P (neutral): 1.79; MH+: 262; 1H-NMR (400 MHz, D6-DMSO) delta ppm: 7.85-7.39 (m, 2H), 3.34-2.92 (m, 2H), 1.39-1.15 (m, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 1052714-48-3.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHSAFT; FISCHER, RUEDIGER; WILCKE, DAVID; KAUSCH-BUSIES, NINA; HAGER, DOMINIK; ILG, KERSTIN; HOFFMEISTER, LAURA; WILLOT, MATTHIEU; PORTZ, DANIELA; GOERGENS, ULRICH; TURBERG, ANDREAS; (161 pag.)US2018/271099; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 105166-53-8 , The common heterocyclic compound, 105166-53-8, name is [2,2′-Bipyridin]-3-amine, molecular formula is C10H9N3, 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.

General procedure: Trifluoroacetic acid (0.75 mL, 0.009 mol) was added to a cooled (0 C) solution (4.5 mL CH2Cl2) of3-amino-2,2?-bipyridine (0.513 g, 0.003 mol), followed by isoamyl nitrite (0.61 mL, 0.004 mol). After 1 h,the diazonium salt of 3-amino-2,2?-bipyridine was precipitated out by cooling the reaction mixtureto -78 C, followed by the addition of diethyl ether (30 mL). The precipitate was filtered. A sample(2 mmol; 0.27 g) of indol-2-one was dissolved in dilute potassium hydroxide solution (15 mL) andcooled in a saltice bath and then cold diazonium solution was added to this cooled solution portionwise by stirring. The solution was further stirred at 0-5 C for 1 h. The pH of the reaction mixturewas maintained at 4-6 by the addition of solid sodium acetate in portions. The mixture was stirredfor 24 h at room temperature. The resulting solid was filtered, washed with cold water, and air-dried.Crystallization from ethanol gave yellow crystalline.(Z)-3-(2-(2,2?-bipyridin-3-yl)hydrazono)indolin-2-one (3), yellow solid (328 mg, 52%): 1H-NMR (600 MHz,DMSO): delta15.70 (s, 1H), 10.89 (s, 1H), 8.80 (d, J = 4.0 Hz, 1H), 8.50 (d, J = 8.1 Hz, 1H), 8.45 (dd, J = 8.4,1.3 Hz, 1H), 8.37 (dd, J = 4.3, 1.4 Hz, 1H), 8.04-7.98 (m, 1H), 7.62 (d, J = 7.4 Hz, 1H), 7.54-7.46 (m, 1H),7.25 (dd, J = 7.6, 6.7 Hz, 1H), 7.04 (t, J = 7.2 Hz, 1H), 6.92 (d, J = 7.7 Hz, 1H). 13C-NMR (151 MHz,DMSO) delta161.83, 156.74, 147.04, 142.28, 140.39, 139.61, 137.59, 137.13, 130.36, 128.95, 125.16, 123.13,121.90, 121.74, 121.61, 121.27, 119.08, 110.29. Elem. anal. calcd. for C18H13N5O, C 68.56, H 4.16, N 22.21.Found: C 68.48, H 4.09, N 21.88. IR (ATR) nu/cm-1: 3180, 3047, 1693, 1464, 1164, 798. m.p: 238-240 C.

The synthetic route of 105166-53-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; ?andrik, Robert; Tisovsky, Pavol; Csicsai, Klaudia; Donovalova, Jana; Gaplovsky, Martin; Sokolik, Robert; Filo, Juraj; Gaplovsky, Anton; Molecules; vol. 24; 14; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 80537-07-1, 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. 80537-07-1, name is 2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid, molecular formula is C14H10N2O2, 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.

EXAMPLE 56 STR62 Thionyl chloride (240 mg) was added dropwise to a stirred mixture of 2-phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid [compound (I)](320 mg) and N,N-dimethylformamide (one drop) in chloroform (10 ml), and then stirred under reflux for 4 hours. After cooling the mixture, chloroform was evaporated in vacuo to give acid chloride of compound (I). Triethylamine (338 mg) was added to a suspension of the acid chloride of compound (I) in methylene chloride (10 ml) under ice-cooling, and to this suspension a solution of 2-ethylpiperidine in methylene chloride was added dropwise. The mixture was stirred under ice-cooling and stood at room temperature overnight. Saturated sodium chloride aqueous solution (20 ml) was added to the mixture and extracted with chloroform (20 ml). The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (8 g) with chloroform as an eluent. The fractions containing the objective compound were combined and evaporated in vacuo to give 1-(2-phenylpyrazolo[1,5-a]pyridin-3-ylcarbonyl)-2-ethylpiperidine (263 mg). mp: 182-183 C. IR (Nujol): 1630, 1600, 1520 cm-1 NMR (DMSO-d6, delta): 0.69 (3H, t, J=7.0Hz), 1.12-1.93 (8H, m), 2.73-3.17 (1H, m), 3.69-4.45 (2H, m) 7.07 (1H, td, J=7.0Hz and 2.0Hz), 7.29-8.00 (7H, m), 8.86 (1H, dd, J=7.0Hz and 1.0Hz) Analysis Calcd. for C21 H23 N3 O: C 75.65, H 6.95, N 12.60 Found: C 75.75, H 7.01, N 12.66

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 80537-07-1, 2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US5102869; (1992); 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. 1122-61-8, name is 4-Nitropyridine, molecular formula is C5H4N2O2, 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. COA of Formula: C5H4N2O2

Example 15 4-Nitropyridine (124 mg, 1 mmol) and O-methylhydroxylamine (71 mg, 1.5 mmol) were dissolved in DMF (2 ml), and a resulting solution was added dropwise to a DMF solution (3 ml) containing potassium tert-butoxide (336 mg, 3 mmol) and zinc (II) chloride (136 mg, 1 mmol) at 25 C. After completion of the addition, the resulting mixture was at 25 C. for one hour and an aqueous saturated ammonium chloride solution (50 ml) was added, followed by extraction with ethyl acetate (80 ml). A resulting organic layer was dried over anhydrous magnesium sulfate, and then isolated and purified by subjecting to silica gel thin layer chromatography (eluent: ethyl acetate/hexane=1/1] to obtain 35 mg of 3-amino-4-nitropyridine (yield: 25%).

With the rapid development of chemical substances, we look forward to future research findings about 1122-61-8.

Reference:
Patent; Sumitomo Chemical Company, Limited; US5648496; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 132834-56-1, 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 132834-56-1, name is 1-(6-Chloro-5-(trifluoromethyl)pyridin-2-yl)piperazine. This compound has unique chemical properties. The synthetic route is as follows.

To a 16 mm test tube was added; 0.5 mmol of the appropriate alcohol or thiol0.4 mmol of the appropriate 6-chloro 5-trifluoromethyl-2-piperazinylpyridine in DMSO (0.5 mL) 0.65 mmol of K-t-BuO in DMSO (1.0 mL) The reactions were stirred at room temperature for two hours followed by addition of HOAc (1.25 mmol, 75 L). The solvent was evaporated at reduced pressure over night (Speed Vac). The remaining solids were dissolved in water/acetonitrile/HOAc, filtered, and the products were purified with preparative HPLC. Mass detection was obtained by a Micro Mass LCP with electrospray positive ionization mode. The analytical HPLC-chromatograms were performed on a Hewlett Packard 1100 with a 504.6 mm Grom-SIL 100 ODS 0 AB, 3 m column and a 504.6 mm YMC-AQ 5 m column. Different gradients of 0.1% TFA in water and acetonitrile were used and the peaks were detected at 254 nm. The area % under the largest peak was reported as the purity.

According to the analysis of related databases, 132834-56-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nilsson, Bjorn M.; Ringberg, Erik; US2003/232814; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65515-39-1, 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. 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile. A new synthetic method of this compound is introduced below.

(a) 2-methoxy-6-methyl-4-(pent-4-en-l-yl)nicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (1.115 g, 6.87 mmol) in THF (20 mL) was added LiHMDS (1 M in toluene, 7.22 mL, 7.22 mmol) at 0 C dropwise via syringe over 10 min, and the reaction was stirred at this temperature for 1 h. 4- Bromobut-l-ene (0.733 mL, 7.22 mmol) was added dropwise via syringe and the mixture was stirred from 0 C to room temperature overnight. The reaction was poured into saturated aqueous ammonium chloride (50 mL) and extracted with EtOAc (3 x 75 mL). The combined organics were dried over Na2S04, filtered, concentrated, and the residue purified by flash chromatography (0-20% EtOAc in hexanes, 40-g column, product fractions pooled and recolumned 0-10% EtOAc in hexanes, 40-g column) to afford 2- methoxy-6-methyl-4-(pent-4-en-l-yl)nicotinonitrile (619 mg, 42%) as a colorless oil. LC- MS(ES) m/z = 217 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,65515-39-1, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (2014); 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. 59944-76-2, name is Thieno[2,3-b]pyridine-2-carboxylic acid, molecular formula is C8H5NO2S, 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. Recommanded Product: Thieno[2,3-b]pyridine-2-carboxylic acid

Coupling: Example 13 is obtained as a white salt (9% yield) using acid C102 according to Method A with non-critical changes. HRMS (FAB) calculated for C15H17N3OS+H: 288.1170, found 288.1175 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 59944-76-2.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem