Day: March 18, 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.849353-19-1, name is 5-Iodo-2-methylpyridin-4-amine, molecular formula is C6H7IN2, molecular weight is 234.04, as common compound, the synthetic route is as follows.SDS of cas: 849353-19-1

General procedure: Step 1: A vial equipped with a magnetic stir bar was charged with the ortho-haloaminopyridine and BrettPhos G1 precatalyst (6 mol %). The vial was sealed with a teflon screw cap, and evacuated and backfilled with argon three times. The amine (1 to 1.5 mol eq) was added via syringe, followed by LiHMDS solution (1M in THF, 2.5 mol eq). Amines that were solid at room temperature were added with the catalyst. The reaction mixture was stirred at 40 C for 4-18 h, until LC/MS indicated complete conversion of the starting material. The mixture was cooled to room temperature, diluted with dichloromethane, and poured into water. The organic phase was separated and the aqueous phase was extracted twice more with dichloromethane. The combined organic phases were dried over Na2SO4. The solvent was removed under reduced pressure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,849353-19-1, 5-Iodo-2-methylpyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Article; Li, Chaomin; Chen, Lily; Steinhuebel, Dietrich; Goodman, Andrew; Tetrahedron Letters; vol. 57; 25; (2016); p. 2708 – 2712;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1010422-51-1, Adding some certain compound to certain chemical reactions, such as: 1010422-51-1, name is 5-Bromo-4-methyl-2-(trifluoromethyl)pyridine,molecular formula is C7H5BrF3N, 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 1010422-51-1.

A mixture of 5-bromo-4-methyl-2-(trifluoromethyl)pyridine (150 mg, 625 mumol), bis(pinacolato)diboron (189 mg, 729 mumol), Pd(dppf)Cl2 (89 mg, 106 mumol) and potassium acetate (120 mg, 1.25 mmol) in dioxane (1 mL) was stirred under N2 at 90 C. overnight. Aqueous NH4Cl was added and the mixture was extracted with CH2Cl2. The combined organic layers were dried and the volatiles were removed under reduced pressure to yield the desired compound which was used in the next step without further purification.

According to the analysis of related databases, 1010422-51-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; VOSS, FELIX; NORDHOFF, SONJA; WACHTEN, SEBASTIAN; WELBERS, ANDRE; RITTER, STEFANIE; US2015/166505; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 72617-82-4, 6-(2,2,2-Trifluoroethoxy)pyridin-3-amine, 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, 72617-82-4, blongs to pyridine-derivatives compound. name: 6-(2,2,2-Trifluoroethoxy)pyridin-3-amine

EXAMPLE 3 N-[2-(2,2,2-Trifluoroethoxy)-5-pyridyl]-1,3-dithietan-2-imine 8.8 g (0.048 mol) 2-(2,2,2-Trifluoroethoxy)-5-aminopyridine and 3.50 g (0.046 mol) carbon disulphide were combined. Over 5 minutes, 4.65 g (0.046 mol) triethylamine was added, dropwise. The reaction mixture was then stirred at 70 C. for 1 hour. After this 50 ml diethyl ether was added at room temperature. The resulting crystals were separated and dried. 12.0 g (70.6% of theory) triethylammonium N-[2-(2,2,2-trifluoroethoxy)-5-pyridyl]dithiocarbamate was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,72617-82-4, its application will become more common.

Reference:
Patent; Schering Aktiengesellschaft; US4897415; (1990); 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 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

1-116: 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (800 mg, 3.48 mmol) was dissolved in DMF (16 mL). Tetrakis(triphenylphosphine)palladium(0) (462 mg, 0.400 mmol), potassium carbonate (2.07 g, 15.0 mmol), and 2,2-dimethylethenylboronic acid pinacol ester (0.82 mL, 4.0 mmol) were added. Argon was bubbled through the mixture for 5 min. The mixture was heated to 120C in a microwave reactor for 1 h. The mixture was diluted with sat’d ammonium chloride (10 mL) then extracted with EtOAc (3×5 mL). The combined organics were dried over sodium sulfate and concentrated. The resulting crude material was purified by silica gel chromatagraphy using 0-40% EtOAc in heptanes as the gradient to provide compound 1-116.

With the rapid development of chemical substances, we look forward to future research findings about 886365-06-6.

Reference:
Patent; EXELIXIS, INC.; XU, Wei; (170 pag.)WO2017/4609; (2017); 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 6945-67-1, name is 2-Bromo-4-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H3BrN2O2

(Step 1) 4-Nitro-2-tetrahydropyran-4-yl-pyridine (0323) (0324) Zinc (19.2 g, 293 mmol) was heated at 210 C. for 10 minutes, cooled to 70 C., then heated to 210 C. again, and the resulting mixture was stirred for 10 minutes. The reaction mixture was cooled to room temperature, then a solution of N,N-dimethylformamide (100 ml) and dibromoethane (6.87 g, 33.6 mmol) in N,N-dimethylformamide (10.0 ml) was added thereto, and the resulting mixture was stirred at 90 C. for 30 minutes. The reaction mixture was cooled to room temperature, then trimethylsilyl chloride (800 mg, 7.30 mmol) was added thereto, and the resulting mixture was stirred at room temperature for 10 minutes. A solution of 4-iodine tetrahydropyran (10.4 g, 49.2 mmol) in N,N-dimethylformamide (60.0 ml) was added to the reaction liquid, and the resulting mixture was stirred at 35 C. for 90 minutes. This zinc derivative was added to a suspension of 2-bromo-4-nitro-pyridine (5.00 g, 24.6 mmol) and Pd(PPh3)2Cl2 (2.60 g, 3.70 mmol) in N,N-dimethylformamide (80.0 ml), and the resulting mixture was stirred in the presence of nitrogen gas at 90 C. for 2 hours. The reaction mixture was cooled to room temperature, then the reaction solution was filtered, and the obtained filtrate was diluted with water (600 ml) and extracted with ethyl acetate (200 ml×3). The extracts were combined, washed with a saturated saline solution, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=10:1 to 5:1) to obtain the title compound (900 mg, 17%). (0325) 1H NMR (CDCl3, 400 MHz): delta 8.85 (d, J=5.6 Hz, 1H), 7.90-7.86 (m, 2H), 4.15-4.11 (m, 2H), 3.61-3.54 (m, 2H), 3.16-3.10 (m, 1H), 2.00-1.91 (m, 4H)

With the rapid development of chemical substances, we look forward to future research findings about 6945-67-1.

Reference:
Patent; Ajinomoto Co., Inc.; UENO, Hirokazu; YAMAMOTO, Takashi; MIYAZAWA, Tomoko; SHINKAI, Kenji; ARISAKA, Harumi; TAKANOHASHI, Toshiyuki; (122 pag.)US2016/244451; (2016); 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. 76041-79-7, name is 5-Bromo-3-(trifluoromethyl)pyridin-2-ol, the common compound, a new synthetic route is introduced below. HPLC of Formula: C6H3BrF3NO

Step 1 : 5-Bromo-2-chloro-3-(trifluoromethv0pyridine (P46a)A solution of compound P45a (11.0 g, 45.8 mmol) in phenylphosphonicdichloride (22 mL) was heated at 140C overnight, cooled to rt, poured into ice water and extracted with EA. The organic layer was washed with sat. aq. NaHC03 and brine consecutively, dried over NaS04, filtered, concentrated and purified by CC (PE/EA = 5/1) to give compound P46a (10.5 g, 88%) as a yellow liquid.

The synthetic route of 76041-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2012/139775; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89167-34-0, 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. 89167-34-0, name is 4-Chloro-3-iodopyridine. A new synthetic method of this compound is introduced below.

Step 1. 4-(2-fluoro-4-nitrophenoxy)-3-iodopyridine (52)[00376] To a stirred solution of 47 (346 mg, 1.445 mmol) in diphenyl ether (6 ml) was added sodium carbonate (459 mg, 4.34 mmol) and 2-fluoro-4-nitrophenol (681 mg, 4.34 mmol). The reaction mixture was heated to 17O0C for four hours then cooled-down to room temperature. The reaction mixture was diluted with dichloromethane, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (0% to 35% EtOAc in hexanes) to afford the title compound 52 (400 mg, 1.1 11 mmol, 77%) as a yellow solid. MS: 361.0 (M+ 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89167-34-0, 4-Chloro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; METHYLGENE, INC.; RAEPPEL, Stephane; SAAVEDRA, Oscar; CLARIDGE, Stephen; VAISBURG, Arkadii; GAUDETTE, Frederic; ISAKOVIC, Ljubomir; DEZIEL, Robert; WO2008/46216; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 166331-65-3, Adding some certain compound to certain chemical reactions, such as: 166331-65-3, name is 2-Chloro-6-isopropylnicotinic acid,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 166331-65-3.

Preparation Example 10 2-Chloro-6-isopropylnicotinic acid (312 g), palladium carbon(10%) (16.0 g) and ethanol-water (6:1) (2000 mL) were stirred under a hydrogen atmosphere at room temperature for 3 days. The reaction solution was filtrated, and the filtrate was concentrated under reduced pressure. Ethyl acetate and a small amount of ethanol were added to the residue, and the precipitated solid was collected by filtration. The solid was added to cooled 1N-aqueous sodium hydroxide solution (1130 mL) and, after dissolution, the precipitated solid was collected by filtration. This was dissolved in chloroform, and dried over magnesium sulfate. The solvent was evaporated, the residual solid was suspended in hexane and collected by filtration to give 6-isopropylnicotinic acid (152 g) as white powder crystals. 1H-NMR(CDCl3)delta: 1.37(6H,d,J=6.9Hz), 3.29(1H,sept,J=6.9Hz), 7.38(1H,d,J=8.1Hz), 8.40(1H,dd,J=2.1,8.1Hz), 9.33(1H,d,J=2.1Hz).

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. 166331-65-3, 2-Chloro-6-isopropylnicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mitsubishi Pharma Corporation; EP1852431; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 61494-55-1, 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid, molecular formula is C7H6ClNO2, 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.

To a stirred solution of diisopropyl amine (1.65 mL, 1 1.7 mmol) in anthydrous THF (10 mL) cooled to -15C was added n-butyl lithium (2.5 M in hexanes, 4.80 mL, 12.0 mmol) slowly between -10C and 0C. The resultant mixture was stirred at room temperature for 15 minutes before being cooled to 0C. The solution of LDA thus formed was added to a rapidly stirred suspension of 2-(2-chloropyridin-3-yl)acetic acid (1.00 g, 5.8 mmol) in anhydrous THF( 20 mL ) at 0C. Upon complete addition of the LDA solution the resultant bright yellow suspension was stirred at 0C for 15 minutes. A solution of (3-fluoro-4- isothiocyanatophenyl)(methyl)sulfane (1.63 g, 8.2 mmol) in anhydrous THF (10 mL) was then added to the reaction mixture and heated to 65C for 18 hours. The reaction mixture was cooled to room temperature and the volatiles removed in vacuo. The resultant brown gum was redissolved in THF, cooled to 0C and 10% aq acetic acid 10 mL added slowly. Acetonitrile (5 mL) was added slowly until a yellow solid developed, the solid was isolated by filtration and washed with ether and acetonitrile to give the title compound as a yellow solid (546mg, 20%). LC/MS: [M+l] 335. ‘HNMR ( 300 MHz, DMSO-d6): d 8.34 ( d, J=8.1 Hz, 1 H ), 7.85-8.20 ( m, 1H ), 7.61 ( t, J = 8.6 Hz, 1H ), 7.39-7.30 ( m, 2H ), 7.21 (d, J = 9.2 Hz, 1H ), 2.52 (s, 3H).

According to the analysis of related databases, 61494-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NFLECTION THERAPEUTICS, INC.; KINCAID, John; NEWSAM, John; KISAK, Edward; WOOTTON, Michael; KUSHWAHA, Avadhesh; (364 pag.)WO2020/106304; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 917364-11-5, Adding some certain compound to certain chemical reactions, such as: 917364-11-5, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid,molecular formula is C8H10N2O2, 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 917364-11-5.

Example 91N-((ls,4s)-4-(2-(3′-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)-4′-hydroxybiphenyl-3- yloxy)-5-fluoronicotinamido)cyclohexyl)-5,6,7,8-tetr ahydroimidazo [ 1 ,2-a] pyridine-2- carboxamide To a solution of 5,6,7, 8-tetrahydroimidazo[l,2-a]pyridine-2-carboxylic acid (28.4 mg, 0.17 mmol) in acetonitrile (5 niL) was added DIPEA (0.057 niL, 0.34 mmol) and HATU (65.1 mg, 0.17 mmol). The mixture was allowed to stir at RT for 10 min before a solution of N-((ls,4s)- 4-aminocyclohexyl)-2-(3′-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)-4′-hydroxybiphenyl- 3-yloxy)-5-fluoronicotinamide (100 mg, 0.17 mmol) in acetonitrile (5 mL) with DIPEA (0.057 mL, 0.34 mmol) was added and the mixture stirred at RT for 30 mins. The reaction mixture was diluted in EtOAc (10 mL), washed with water, brine, dried (MgSO4) and evaporated to give a foam. This was purified by preparative HPLC to afford the title compound as a white solid. Yield: 31 mg1H NMR (400 MHz, CD3OD) delta 8.42 (d, J= 6.9 Hz, IH), 8.11 – 8.06 (m, 2H), 7.75 (s, IH), 7.57 – 7.42 (m, 4H), 7.38 (s, IH), 7.15 – 7.08 (m, IH), 6.92 (d, J= 8.5 Hz, IH), 4.16 – 4.07 (m, 5H), 3.98 – 3.89 (m, IH), 3.62 – 3.52 (m, 2H), 3.44 (d, J= 12.8 Hz, 2H), 2.95 (t, J= 6.2 Hz, 2H), 2.67 (t, J= 12.6 Hz, 2H), 2.10 – 1.64 (m, 12H), 1.32 (d, J= 6.7 Hz, 6H). MS: [M+H]+=696.4 (calc=696.3673) (MultiMode+)

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. 917364-11-5, 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem