Pyridine-derivatives

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. 1124-29-4, name is 5-Acetylpyridin-2(1H)-one, molecular formula is C7H7NO2, 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. HPLC of Formula: C7H7NO2

General procedure: [0561] To a solution of III-3 (1 eq.) in DCM (0.1 mmol/mL) was added boronic acid III-4 (2 eq.), Cu(OAc)2 (1 eq), Pyridine (10 eq.) and Pyridine-N-Oxide (2 eq.), followed by addition of 4 molecular sieve (quantity approx. equal to III-3). The reaction mixture was stirred at rt under oxygen atmosphere overnight. After completion of the reaction indicated by TLC, the resulting mixture was filtered and washed with, the filtrate was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel to give III-5. [0562] Compound 10 (61% yield): 1H NMR (DMSO-d6, 400 MHz) delta 8.43 (d, J=2.4 Hz, 1H), 7.90 (dd, J=9.6, 2.4 Hz, 1H), 7.39 (d, J=8.8 Hz, 2H), 7.06 (d, J=8.8 Hz, 2H), 6.51 (d, J=9.6 Hz, 1H), 3.81 (s, 3H), 2.41 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 1124-29-4.

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Ramphal, Johnnie Y.; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/94456; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid, 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 C7H6ClNO2, blongs to pyridine-derivatives compound. Computed Properties of C7H6ClNO2

Example 4 Synthesis of N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloro-3-methylpicolinamide The title compound was synthesized by procedures and steps analogous to those described in Method A in Example 2 above, but using 5-chloro-3-methylpicolinic acid (Intermediate 6) in step 1. MS m/z=463.0 [M+H]+. Calculated for C19H16ClF5N4O2: 462.801 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.22 (t, J=13.20 Hz, 1H) 2.73 (dd, J=13.60, 2.64 Hz, 1H) 2.79 (s, 3H) 4.14-4.22 (m, 1H) 4.41-4.58 (m, 1H) 4.63-4.79 (m, 1H) 7.11 (dd, J=11.54, 9.00 Hz, 1H) 7.47 (dd, J=6.94, 2.84 Hz, 1H) 7.65 (d, J=1.76 Hz, 1H) 8.08 (ddd, J=8.85, 4.16, 2.84 Hz, 1H) 8.39 (d, J=1.76 Hz, 1H) 10.04 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); 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 83664-33-9, name is 2-(Benzyloxy)-5-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-(Benzyloxy)-5-bromopyridine

To a solution of [2-BENZYLOXY-5-BROMO-PYRIDINE] (1.64 g, 6.2 mmol) in tetrahydrofuran (25 [ML,-78C)] was added n-butyllithium (2.5 M in hexane, 2.61 mL, 1.05 equiv). After 1 h [AT-78C,] dimethylformamide (0.97 mL, 2 equiv) was added and the mixture stirred for 30 min. The reaction was quickly poured into a stirred solution of 5% aqueous sodium bicarbonate (50 [ML)] and extracted with diethyl ether [(-3X).-THE ETHEREAL-WAS WASHED-WITH BRINE, DNeD-OVER MaGNESIUM~SULFATE, AND] concentrated to give 1.16 g (quant. ) which was used without purification. Mass spec.: 186.34 [(MH)] [+.]

With the rapid development of chemical substances, we look forward to future research findings about 83664-33-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/104236; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 170235-18-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 170235-18-4 as follows.

(1) 3-(trifluoromethyl) phenol (1.317 g, 0.0081 mol) was dissolved in 10 ml of dried dimethyl acetamide. While cooling the obtained solution with water, sodium hydride (0.39 g (ca. 60% in mineral oil), 0.0081*1.2 mol) was added to the solution. After completion of the foaming, a solution obtained by dissolving 6-bromo-5-methoxy-2-pyridine carboxylic acid methyl ester (2.0 g, 0.0081 mol) in 10 ml of dried dimethyl acetamide, and then copper iodide (1.55 g, 0.081 mol) were successively added to the solution. The obtained mixture was heated and stirred at 120 C. for 10 hours. Thereafter, the obtained reaction solution was cooled, mixed with 50 ml of water and then with 50 ml of ethyl acetate, and filtered through a glass filter provided with Hyflo Super-Cell. The obtained filtrate was extracted with ethyl acetate to obtain an aimed product. An organic phase was separated from the product, washed with water and then dried with anhydrous sodium sulfate. The dried product was concentrated, and the obtained residues were purified by silica gel column chromatography (eluding solution: ethyl acetate/hexane). Yield weight: 0.68 g; yield percentage: 26%; solid; melting point: 116 to 118 C.; 1 H-NMR (60 MHz, CDCl3, delta): 3.76(3H, s), 3.86(3H, s), 7.16(1H, d, J=8 Hz), 7.2-7.5(4H, complex), 7.80(1H, d, J=8 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,170235-18-4, its application will become more common.

Reference:
Patent; Kureha Kagaku Kogyo Kabushiki Kaisha; US6159901; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 3222-56-8, 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 3222-56-8, name is 2-Methylnicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

29) 2-methylnicotinamideTo a solution of 2-methylnicotinic acid (0.537 mg, 3.9 mmol) in 20 mL of DMF at 0 0C was added HATU (1.56 g, 4.1 mmol) followed by the dropwise addition of DIPEA (0.72 ml, 4.1 mmol). NH3(g) was then bubbled into the solution for 15 mins. The reaction was o allowed to stir overnight. The resulting paste was filtered and rinsed with cold DMF and discarded. The mother liquor was concentrated and purified by normal phase chromatography using CH2Cl2/7 N NH3 in MeOH: 93/7 as eluent. Yielded a white solid (405 mg, 76 %). IH NMR (400 MHz, CHLOROFORM-D) delta ppm 1.34 (s, 9 H), 1.36 (d, J=6.64 Hz, 3 H), 2.56 (s, 3 H), 4.32 – 4.40 (m, 1 H), 7.15 – 7.19 (m, J=8.20 Hz, 1 H), 7.68 (d, J=8.20 Hz, s I H)

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 3222-56-8, 2-Methylnicotinic acid.

Reference:
Patent; ASTRAZENECA AB; WO2007/73303; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1000341-55-8 ,Some common heterocyclic compound, 1000341-55-8, molecular formula is C7H4ClIN2, 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) Preparation of intermediate 10A stirred solution of 6-chloro-3-iodo-5-azaindole (1.00 g, 3.56 mmol) in DMF (35 ml) at 0 C, was treated with sodium hydride (60%> in mineral oil, 0.17 g, 4.31 mmol). After stirring at 0 C for 10 minutes, the mixture was treated with p-toluenesulfonyl chloride (0.75 g, 3.95 mmol), then warmed to ambient temperature over 30 minutes. The reaction was quenched by the addition of water, then partitioned between EtOAc and dilute aqueous sodium bicarbonate solution. The organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with a mixture of EtOAc and cyclohexane (0: 1 to 6:4 by volume), to afford the desired product as a white solid (1.18 g, 76%).LCMS (Method B): Rt= 4.19 min, m/z [M+H]+= 433/435

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. 1000341-55-8, 6-Chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HYND, George; TISSELLI, Patrizia; CLARK, David, Edward; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; PANCHAL, Terry, Aaron; PRICE, Stephen, Colin; MONTANA, John, Gary; WO2015/44267; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6515-09-9, Adding some certain compound to certain chemical reactions, such as: 6515-09-9, name is 2,3,6-Trichloropyridine,molecular formula is C5H2Cl3N, 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 6515-09-9.

18.4 g (0.1 mol) 2,3,6-trichloropyridine was dissolved in 70 g glacial acetic acid and 0.54 g molybdenum trioxide was added,The temperature was raised to 80 C, 13.6 g (0.12 mol) of hydrogen peroxide (30%) was slowly dropped,Full response, liquid chromatography control, the reaction is over, the catalyst was filtered, the filtrate was concentrated to recover acetic acid, 2,3,6-trichloropyridine nitrogen oxide 18.2g, yield 90%.

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. 6515-09-9, 2,3,6-Trichloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Hong Sun Biochemical Co., Ltd.; Jiang Jianhua; Yue Ruikuan; Jiang Tao; Chen Honglong; Luo Chaoran; (6 pag.)CN106243027; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1839-17-4, 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 1839-17-4, name is N4-Methylpyridine-3,4-diamine. This compound has unique chemical properties. The synthetic route is as follows.

(d) N-(4-methylamino-3-pyridyl)-N’-cyclohexylthiourea Cyclohexyl isothiocyanate (1.09 ml, 7.71 mmol) was added to a solution of 3-amino-4-methylaminopyridine (950 mg, 7.71 mmol) in DMF (5 ml), and the mixture was stirred at room temperature for 1 hour and at 120 C. for 3 hours. After removal of the solvent, the residue was subjected to silica gel column chromatography (eluent: chloroform_methanol=10:1 (v/v)) and recrystallization to purify it, thereby obtaining 98 mg of the intended product as flesh-colored crystals. m.p.: >250 C. IR (KBr): 3500-3000, 2920, 1600 cm-1 1 H-NMR (CDCl3) delta ppm: 1.0-2.1 (10H, m), 2.89 (3H, d, J=4.0 Hz). 4.1-4.4 (1H, m), 4.93 (1H, d, J=4.0 Hz), 5.72 (1H, d, J=6.0 Hz), 6.56 (1H, d, J=6.0 Hz), 7.65 (1H, s), 8.10 (1H, s), 8.26 (1H, d, J=6.0 Hz) 13 C-NMR (CDCl3) delta ppm: 24.5, 25.1, 28.7, 32.2, 53.8, 105.2, 118.0, 147.4, 149.0, 151.7, 179.9

According to the analysis of related databases, 1839-17-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Green Cross Corporation; US5371086; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 66909-38-4, 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.66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine, molecular formula is C6H7ClN2, molecular weight is 142.5862, as common compound, the synthetic route is as follows.

A mixture OF 4-(6-CHLORO-5-METHYL-PYRIMIDIN-4-YLOXY)-PIPERIDINE-1-CARBOXYLIC acid isopropyl ester (1.80 g, 5.74 mmol), palladium acetate (155 mg, 0.69 mmol), biphenyl-3-yl-di-tert-butyl- phosphane (21.5 mg, 0.072 mmol), sodium tert-butoxide (1.38 g, 14.4 mmol), and 6-CHLORO-4-METHYL- pyridin-3-ylamine (838 mg, 5.80 mmol) in 20 mL dioxane was heated in microwave for 1 hour at 120C. Solids were filtered off and mixture was purified by column chromatography (hexane/AcOEt) to give Compound A98 as a tanned solid (702 mg, 29%). H NMR (CDCL3, 400 MHz) 8 1.24-1. 26 (d, 6H), 1.72-1. 81 (M, 2H), 1.95-2. 02 (M, 2H), 2.10 (s, 3H), 2.27 (s, 3H), 3.37-3. 43 (M, 2H), 3.74-3. 77 (M, 2H), 4.90-4. 97 (m, 1H), 5.29-5. 34 (M, 1H), 5.91 (s, 1H), 7.00 (s, 1H), 8.22 (s, 1H), 8.57 (s, 1H). Exact mass calculated for C2OH26CIN503 419.17, found 420.4 (MH+).

The chemical industry reduces the impact on the environment during synthesis 66909-38-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2005/7647; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153747-97-8, 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. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate. A new synthetic method of this compound is introduced below.

The compound (R)-N,N-bis(tert-butoxycarbonyl)-3-(1-(2-chloro-3,6-difluorophenyl)ethoxy)-5-(4,4,5 ,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.89 g, 1.46 mmol)Dissolved in DME (10 mL),Then, tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (0.5 g, 1.46 mmol) was added to the reaction mixture.Cesium carbonate (1.43g, 4.38mmol),Water (2mL) andPd(dppf)Cl2.CH2Cl2 (120 mg, 0.15 mmol).After the reaction system was purged with nitrogen (nitrogen) three times,Stir at 100C overnight,Then add ethyl acetate (50 mL)Diluted the reaction solution with water (12 mL).The layers were separated, the aqueous phase was extracted with ethyl acetate (50 mL x 2), and the combined organic phases were washed with saturated brine (25 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The resulting residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether (v/v) = 1/1)The title compound was obtained as a yellow oil (0.69 g, 63%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153747-97-8, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wang Tingjin; (104 pag.)CN104650049; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem