Pyridine-derivatives

Application of 34486-24-3, Adding some certain compound to certain chemical reactions, such as: 34486-24-3, name is 2-Amino-6-(trifluoromethyl)pyridine,molecular formula is C6H5F3N2, 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 34486-24-3.

To a mixture of 6-(trifluoromethyl)pyridin-2-amine (600 mg, 3.7mmol) in MeOH (10 mL) was added NBS (659 mg, 3.7mmol) in portions at 0oC. The reaction mixture was stirred at r.t. overnight. The reaction mixture was concentrated under reduced pressure and the residue was purified by chromatography (eluted with PE:EA = 4:1) to afford the title compound (650 mg, 73.1% yield) as a white solid. Retention time (LC-MS): 1.33 min. MH+ 241.

According to the analysis of related databases, 34486-24-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HYDRA BIOSCIENCES, INC.; CHENARD, Bertand, L.; WU, Xinyuan; (351 pag.)WO2016/44792; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 63237-88-7, 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 63237-88-7 as follows.

To a solution of pyrazolo[1 ,5-a]pyridine-2-carboxylic acid (0.202 g; 1.246 mmol) in dichloromethane (2 mL) were added HATU (0.472 g; 1.241 mmol) and DIPEA (0.450 mL; 2.577 mmol). After stirring for 5 min at room temperature, Lambda/,Omicron-dimethylhydroxylamine hydrochloride (0.128 g; 1.312 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed with water. The phases were separated. The organic phase was washed with a 1 N hydrochloric acid solution, a 1 N sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give N-methoxy-N-methylpyrazolo[1 ,5-a]pyridine-2- carboxamide which was used in the next step without further purification. ESI/APCI (+): 206 (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,63237-88-7, its application will become more common.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim; WO2013/45516; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 185041-05-8 , The common heterocyclic compound, 185041-05-8, name is Methyl 2-chloro-4-iodonicotinate, molecular formula is C7H5ClINO2, 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.

B. Methyl 2-chloro-4-cyanonicotinate A solution of methyl 2-chloro-4-iodonicotinate (3.20 g, 10.76 mmol) and cyanocopper (0.963 g, 10.76 mmol) in DMA (40 mL) was stirred at 140 C. overnight. Following reaction, the mixture was filtered through Celite and the filtrate was diluted with H2O and EtOAc. The aqueous phase was extracted with EtOAc. The organic phases were combined, washed with H2O and brine, dried over MgSO4, and evaporated. The residue was purified by chromatography on SiO2 (Hexane/EtOAc=10/1) to give the title compound as a white solid (730 mg, 34.5%). 1H NMR (500 MHz, CDCl3) delta ppm 4.07 (s, 3H), 7.57 (d, J=5.37 Hz, 1H), 8.66 (d, J=4.88 Hz, 1H).

The synthetic route of 185041-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2011/152273; (2011); 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. 89364-04-5, name is 3-Bromo-4-nitropyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

Example 1 (0052) Non-radioactive fluorination of 3-bromo-4-nitropyridine (3): 10 muL of 1 M tetrabutylammonium fluoride (TBAF) solution in THF (10 mumol, 0.5 eq.) was added to a solution of 3-bromo-4-nitropyridine (96%, Aurum Pharmatech, LLC) (20 mumol, 1 eq.) in 500 L of anhydrous dimethylsulfoxide (DMSO) in a 2 mL HPLC vial. The reaction was analyzed by HPLC (conditions A). Retention times: 3-bromo-4-nitropyridine (3)=10.83 min, 3-fluoro-4-nitropyridine=8.38, 3-bromo-4-fluoropyridine (6)=11.76 min. Retention times for the product matched within 0.05 min the reference standard. Identity of the product was confirmed by HR-MS (m/z M+ exp.: 174.9423, calc: 174.9433) and 1H, 13C and 19F NMR. Product amount was calculated from the area under the curve of the HPLC UV1 trace using a calibration curve.

The synthetic route of 89364-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The University of Chicago; Brugarolas, Pedro; (35 pag.)US2017/355648; (2017); 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.785762-99-4, name is 2-(5-(Trifluoromethyl)pyridin-2-yl)acetic acid, molecular formula is C8H6F3NO2, molecular weight is 205.134, as common compound, the synthetic route is as follows.category: pyridine-derivatives

(6) To a 250 ml single-mouth bottle, 15.8 g (0.282 mol, 1.0 eq) of potassium hydroxide was added.Water 54 ml (1 v / w), stir and dissolve. Compound 785762-99-4 54g (0.282 mol, 1.0 eq) was added to the system and stirred to dissolve. After stirring at 40 C for 1 h, the reaction solution was concentrated. A pale yellow solid powder of 61 g was obtained in a yield of 89%. The nuclear magnetic data is as follows:

At the same time, in my other blogs, there are other synthetic methods of this type of compound,785762-99-4, 2-(5-(Trifluoromethyl)pyridin-2-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Chen Min; (6 pag.)CN108997202; (2018); 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 722550-01-8, name is 4-(Pyrrolidin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C9H13N3

General procedure: Compound 2-(4,5-dichloro-2-methoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 88 was prepared in the same manner as 2-(5-chloro-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 5a. The resulting hydrobromic acid salt was neutralized with dilute aqueous ammonia to obtain free base and as an off-white solid (48 rng, 72%). 1H NMR (400 MHz, CDC13): delta 8.48 (s. 1H), 7.87 (s, 1H), 7.85 (d, J = 7.6 Hz, 1H), 7.02 (s, 1H ), 6.42 (br s, 1H), 6,36 (dd, 1H, J= 2.4 Hz, 7.5), 3.97 (s, 3H), 3,38-3.33 (m, 4H), 2.07-2.03 (m, 4H); HPLC (Method 1) 99,73% (AUC), tR = 1 1,76 min.; APCI MS m/z 362 [ M + H ]+

With the rapid development of chemical substances, we look forward to future research findings about 722550-01-8.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 84487-15-0, Adding some certain compound to certain chemical reactions, such as: 84487-15-0, name is 2-Bromo-5-nitropyridin-4-amine,molecular formula is C5H4BrN3O2, 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 84487-15-0.

A solution of 2-bromo-5-nitropyridin-4-amine (1.5 g, 6.9 mmol) in acetic acid (20 mL) was added in portions into a 75 C suspension of iron powder (1.5 g, 27 mmol) in acetic acid (20 mL). The reaction mixture was stirred at 75 C for 2 h, cooled to room temperature, and filtered through celite. To the filtrate was added 1,3-bis(methoxycarbonyl)-2-methyl-2- thiopseudourea (1.4 g, 6.9 mmol), and the mixture was stirred at 65 C for 60 h. The reaction mixture was cooled to room temperature and concentrated. The solid residue was triturated with dichloromethane and dried to give the title Compound (1.8 g, quantitative yield) as an orange solid. MS (EI) for C8H7BrN4O2: 271/273 (MH+).

According to the analysis of related databases, 84487-15-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; ANAND, Neel, Kumar; BLAZEY, Charles, M.; BOWLES, Owen, Joseph; BUHR, Chris, Allen; BUSSENIUS, Joerg; CURTIS, Jeffry, Kimo; DEFINA, Steven, Charles; DUBENKO, Larisa; HARRIS, Jason, R.; JACKSON-UGUETO, Eileen; JOSHI, Anagha; KIM, Angie, Inyoung; TSUHAKI, Amy, Lew; MA, Sunghoon; MANALO, Jean-claire, Limun; NG, Stephanie; PETO, Csaba, J.; RICE Kenneth D.; TSANG, Tsze, H.; ZAHARIA, Cristiana, A.; WO2010/135524; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 39891-09-3, Adding some certain compound to certain chemical reactions, such as: 39891-09-3, name is 2-Chloropyridine-5-acetonitrile,molecular formula is C7H5ClN2, 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 39891-09-3.

22.0 g (144 mmol) of (6-chloropyridin-3-yl)acetonitrile are added to a mixture of 270 ml of ethanol and 101 ml conc. sulfuric acid, and the mixture is stirred under reflux for 24 h. With stirring, the reaction mixture is then slowly added dropwise to a mixture of 350 g of sodium bicarbonate and 1 liter of water. The aqueous phase is extracted with dichloromethane (five times 400 ml each). The combined organic phases are dried over sodium sulfate, filtered and freed from the solvent using a rotary evaporator. This gives 23.1 g (80% of theory) of the title compound, which is reacted without further purification.1H-NMR (400 MHz, DMSO-d6): delta=8.32 (d, 1H), 7.78 (dd, 1H), 7.49 (d, 1H), 4.10 (q, 2H), 3.77 (s, 2H), 1.19 (t, 3H).LC-MS (Method 3): Rt=1.91 min; MS (ESIpos): m/z=200 [M+H]+.

According to the analysis of related databases, 39891-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Thede, Kai; Flamme, Ingo; Oehme, Felix; Ergueden, Jens-Kerim; Stoll, Friederike; Schuhmacher, Joachim; Wild, Hanno; Kolkhof, Peter; Beck, Hartmut; Akbaba, Metin; Jeske, Mario; US2012/264704; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1060814-91-6 ,Some common heterocyclic compound, 1060814-91-6, molecular formula is C9H10BrNO2, 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.

To a solution of ethyl 2-(4-bromopyridin-2-yl)acetate (1.72 g, 7.05 mmol) in THF (23.49 ml) was added dropwise LDA(4.05 ml, 8.10 mmol, 2M solution in THF) and the resulting mixture was stirred for 40 mm at-78C. Allyl bromide (0.610 ml, 7.05 mmol) was added dropwise, and the stirring was continuedat -78C for 2h and checked by LCMS (little desired product). The reaction mixture was slowly warmed to RT and stirred at RT for lhr (the reaction complete). The reaction was quenched by adding a saturated aqueous solution of NH4C1 (20 mL). The aqueous layer was extracted with Et20 (2 x 20 mL), the organic phases were combined, washed with HC1 (1 M, 20 mL), brine (20 mL), dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by flash column chromatography on silica gel (1/1 EtOAc/Hex) to give the titlecompound. LC/MS = 285.77 [M+lj

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. 1060814-91-6, Ethyl 2-(4-bromopyridin-2-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; LIM, Yeon-Hee; XU, Jiayi; ZHOU, Wei; (123 pag.)WO2017/74833; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 92276-38-5, Adding some certain compound to certain chemical reactions, such as: 92276-38-5, name is 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine,molecular formula is C5H3BrN4, 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 92276-38-5.

General procedure: To a stirred solution of 6-bromo-1H-i,2,3-triazolo[4,5-b]pyridine (250 mg, 1.26 mmol) in DMF (5 mL) at rt was added 60% sodium hydride in mineral oil (55 mg, 1.38 mmol) and the mixture was stirred at rt for 30 mins. (2-(Chloromethoxy)ethyl)trimethylsilane (419 mg, 2.51 mmol) was added and the mixture was stirred for 15 h. The reaction mixture was partitioned between water and EtOAc and the aqueous layer was separated and further extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0 – 20% EtOAc in hexanes to afford a 1:1 mixture of 6-bromo- 1 -((2- (trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5-b]pyridine and 6-bromo-3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo[4,5 -b]pyridine (240 mg) as an oil, which was not purified further. LC-MS (ESI) mlz 329 and 331 (M+H).v [000223] Step 2: A 1:1 mixture of N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 – yl)-2-(4-(l -((2-(trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5 -b]pyridin-6- yl)phenyl)acetamide and N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)-2-(4-(3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo [4,5 -b]pyridin-6-yl)phenyl)acetamide (71 mg, 40%) was obtained as a solid using a procedure analogous to that described in Step 3 of Example4, substituting the product obtained from Step 1 of this example for the 2-chloro-6,7- dimethoxyquinoxaline used in Example 4 and substituting 2-(4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)acetamide (Ref: S. Abraham et al, WO 2011022473 Al) for the 2-(2-fluoro-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1 -(trifluoromethyl)cyclopropyl)isoxazol-3 -yl)acetamide used in Example 4. LC-MS (ESI) mlz 561 (M+H).[000224] Step 3: To a 1:1 mixture of N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 – yl)-2-(4-(l -((2-(trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5 -b]pyridin-6- yl)phenyl)acetamide and N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)-2-(4-(3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo [4,5 -b]pyridin-6-yl)phenyl)acetamide (71 mg, 0.127 mmol) was added trifluoroacetic acid (5 mL), and the mixture was stirred at rt for 1 h. The mixture was concentrated under reduced pressure and the residue was purified by reverse-phase preparative HPLC using a mixture of water (containing 5% CH3CN and 0.05% HCOOH) and CH3CN (containing 0.05% HCOOH) as the mobile phase and Varian Pursuit XRs diphenyl column as the stationary phase to afford 2-(4-(3H-[l,2,3]triazolo[4,5-b]pyridin-6-yl)phenyl)-N- (5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)acetamide (12 mg, 22%) as a solid. ?H NMR (500 MHz, DMSO-d6) oe 11.41 (br s, 1H), 9.00 (d, J= 2.0 Hz, 1H), 8.60 (br s, 1H), 7.80 (d, J 8.5 Hz, 2H), 7.48 (d,J 8.5 Hz, 2H), 6.95 (s, 1H), 3.77 (s, 2H), 1.53 (s, 6H); LC-MS (ESI) m/z 431 (M+H).

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. 92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; HOLLADAY, Mark, W.; LIU, Gang; ROWBOTTOM, Martin, W.; WO2015/31613; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem