Day: April 8, 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.59020-10-9, name is 3-(Tributylstannyl)pyridine, molecular formula is C17H31NSn, molecular weight is 368.1447, as common compound, the synthetic route is as follows.Recommanded Product: 3-(Tributylstannyl)pyridine

A solution containing the product from Example 23I (0.200 g, 0.283 mmol) in DMF (3 mL) was treated with LiCl (0.120 g, 2.83 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.060 g, 0.085 mmol), and 3-tri-r-butylstannlypyridine (0.200 mL, 0.870 mmol), heated at 1001C for 16 hours, cooled and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-25% ethyl acetate in dichloromethane to give the title compound (0.130 g, 72% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59020-10-9, 3-(Tributylstannyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; DeGoey, David A.; Flentge, Charles A.; Flosi, William J.; Grampovnik, David J.; Kempf, Dale J.; Klein, Larry L.; US2005/131017; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 936841-69-9 ,Some common heterocyclic compound, 936841-69-9, molecular formula is C7H3F3N2, 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.

[0209] A mixture of 4-(trifluoromethyl)picolinonitrile (840mg, 4.88 mmol) and 10%Pd/C (168 mg, 0.16 mmol) was stirred under hydrogen (balloon) in MeOH (10 mL) at ambient temperature for overnight. The reaction mixture was filtered through Celite and concentrated to afford (4- (trifluorom ethyl )pyridin-2-yl)methanamine as an oil. LC/MS = 177 [M+l].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,936841-69-9, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUANG, Rongze; TING, Pauline; ALI, Amjad; WU, Heping; BERLIN, Michael; STAMFORD, Andrew; WANG, Hongwu; ZHOU, Gang; KIM, David; DENG, Qiaolin; LIM, Yeon-Hee; YU, Younong; (201 pag.)WO2016/81290; (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.10273-89-9, name is 2-(o-tolyl)pyridine, molecular formula is C12H11N, molecular weight is 169.22, as common compound, the synthetic route is as follows.Product Details of 10273-89-9

General procedure: Unless otherwise stated, in an Argon filled glove-box a crimp-cap microwave vial equipped with a magnetic stirring bar was charged with the appropriate cyclometalated Ru(ll)-catalyst (like Ru1-Ru46, from 3 mol % to 10 mol %), KOAc (5.9 mg, 0.06 mmol, 30 mol %), K2CO3 (2.0 – 4.0 equiv.), the appropriate DG-containing arene (like N1-N12, 0.20 mmol, 1.0 equiv.), the appropriate (hetero)aryl (pseudo)halide (like X1-X42, 0.2 mmol, 1.0 equiv) and /V-methyl-2- pyrrolidone (NMP) (200 pL, 1 M). The vial was capped and stirred at 35 C for 24 hours. Upon completion, the crude mixture was loaded on a silica gel column and purified by flash chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10273-89-9, 2-(o-tolyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; THE UNIVERSITY OF MANCHESTER; LARROSA, Igor; SIMONETTI, Marco; CANNAS, Diego Maria; (94 pag.)WO2019/215426; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 130284-52-5, 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. 130284-52-5, name is 6-Bromo-5-chloropyridin-3-amine, molecular formula is C5H4BrClN2, 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 6-bromo-5-chloropyridin-3-amine (500 mg, 2.41 mmol), 1,1-bis(diphenylphosphino)ferrocene (134 mg, 0.24 mmol) and triethylamine (732 mg, 7.23 mmol) in MeOH (3 mL) and toluene (15 mL) was heated at 70 C. under a CO (35 psi) atmosphere with dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (catalyst, 197 mg, 0.24 mmol), and the mixture was stirred overnight. After uptake of CO (1 equiv), the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to give a crude product. The crude product was purified by flash column chromatography over silica gel (petroleum ether/ethyl acetate from 100/0 to 50/50) to afford compound 43a as a red solid (300 mg, 67%). 1H NMR (400 MHz, CDCl3) delta ppm 3.96 (s, 3H), 4.14-4.24 (m, 2H), 7.03 (d, J=2.26 Hz, 1H), 8.03 (d, J=2.51 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 130284-52-5, 6-Bromo-5-chloropyridin-3-amine.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 66909-38-4, 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 66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

Compound 6-chloro-4-methylpyridin-3-amine 6a (6.75 g, 47.3 mmol), N-iodosuccinimide (12.95 g, 57.6 mmol), and N,N-dimethylformamide (100 mL) were mixed at 0C and stirred at room temperature for 15 hrs. Next, water (100 ml) was added, and the mixture was extracted with ethyl acetate (150 mL*3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered to remove the desiccant, and concentrated to remove solvent under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate= 10/1) to give a target product 6-chloro-2-iodo-4-methylpyridin-3-amine 6b (6.5 g, yellow solid), yield: 47%. MS m/z (ESI):269[M+1]

According to the analysis of related databases, 66909-38-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing InnoCare Pharma Tech Co., Ltd.; CHEN, Xiangyang; PANG, Yucheng; (44 pag.)EP3409672; (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. 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

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

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

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 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