Pyridine-derivatives

Electric Literature of 884495-14-1 ,Some common heterocyclic compound, 884495-14-1, molecular formula is C7H7BrN2O3, 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.

DMF-DMA (600 mL) was slowly added to a stirred and heated (80 C) solution of 5-bromo-2- methoxy-4-methyl-3-nitropyridine (134 g, 0.54 mol) in DMF (1.1 L). After addition, the mixture was heated at 95 C for 5 h, at which time TLC indicated the reaction had gone to completion. The mixture was cooled to room temperature and poured into ice-cold water (3 L). The resulting red solid was collected by filtration, washed with water, and dried under reduced pressure to give the title compound (167 g, 100% yield) as red solid. 1H NMR (400 MHz, DMSO-tM): delta 8.24 (s, 1 H), 7.05 (d, J= 13.6 Hz, 1 H), 7.05 (d, J= 13.6 Hz, 1 H), 4.80 (d, J= 13.2 Hz, 1 H), 3.88 (s, 3 H), 2.90 (s, 6 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-14-1, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; BELLON, Steven, F.; BURDICK, Daniel, J.; COTE, Alexandre; CRAWFORD, Terry; DAKIN, Les, A.; HSIAO-WEI TSUI, Vickie; HEWITT, Michael, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F., Anthony; TANG, Yong; TAYLOR, Alexander, M.; WANG, Shumei; (251 pag.)WO2016/77375; (2016); 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 23056-33-9, name is 2-Chloro-4-methyl-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Chloro-4-methyl-5-nitropyridine

Zinc (15.97 g, 244.0 mmol) was suspended in acetic acid (240 ml) and cooled to 0C. Solid 2-(2-chloro-5-nitropyridin-4-yl)-N,N-dimethylethenamine (5.56 g, 24.42 mmol) was added portion- wise over about 5 minutes and then the reaction mixture was placed under an atmosphere of argon. The reaction was stirred for 18 h, after which time LCMS analysis indicated that the reaction was complete. The mixture was filtered through Celite, washing with EtOAc. The filtrate was concentrated to give a brown oil. The reaction mixture was partitioned between EtOAc and IN NaOH. The aqueous layer was extracted with EtOAc (3x) and the combined organic layer was dried over Na2S04, filtered and concentrated. The residue was adsorbed onto silica gel and purified by flash column chromatography on silica gel, eluting with EtOAc/isohexane (0-100%) to give 2.79 g of an off-white solid, that is approximately a 10: 1 mixture of the title compound along with 5-methoxy-lH-pyrrolo[2,3-c]pyridine as a minor impurity. The mixture was taken forward into the next step as is. LRMS (ESI) calc’d for (C7H5C1N2) [M+H]+, 153; found 153

With the rapid development of chemical substances, we look forward to future research findings about 23056-33-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; FISCHER, Christian; KATZ, Jason, D.; WILLIAMS, Theresa, M.; ZHANG, Xu-Fang; ZHOU, Hua; WO2013/181075; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 113293-71-3, 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.113293-71-3, name is (6-Aminopyridin-3-yl)methanol, molecular formula is C6H8N2O, molecular weight is 124.14, as common compound, the synthetic route is as follows.

To a stirring of (6-aminopyridin-3-yl)methanol (1.24 mg, 10.0 mmol) and ethyl 2-chloro-3-hydroxyacrylate, potassium salt (29) (3.76 g, 20.0 mmol) in EtOH (10 mL) at room temperature was added conc sulfuric acid (10.0 mmol) dropwise. The reaction mixture was stirred at room temperature for 15 minutes and pyridine (0.92 g, 12.0 mmol) was added. The resulting mixture was heated at 85 C. overnight. The reaction was cooled to room temperature and the solvent was concentrated. The residue was taken in water and the solution was adjusted to pH 8 with saturated sodium bicarbonate. The crude product was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The crude product ethyl 6-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxylate (59) was purified by silica chromatography. 1H NMR (400 MHz, d6-DMSO) delta 9.16 (d, J=6.8 Hz, 1H), 8.26 (s, 1H), 7.67 (s, 1H), 7.19 (dd, J=1.6, 6.8 Hz, 1H), 5.57 (t, J=6.4 Hz, 1H), 4.63 (d, J=6.0, 2H), 4.36 (q, J=7.2 Hz, 2H), 1.35 (t, J=6.8 Hz, 3H). MS m/z 221.1 (M+1)+.

Statistics shows that 113293-71-3 is playing an increasingly important role. we look forward to future research findings about (6-Aminopyridin-3-yl)methanol.

Reference:
Patent; MOLTENI, Valentina; PETRASSI, Hank Michael James; LI, Xiaolin; LIU, Xiaodong; LOREN, Jon; NABAKKA, Juliet; NGUYEN, Bao; YEH, Vince; US2013/59832; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 944317-53-7, 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. 944317-53-7, name is 4-Methyl-5-nitro-2-(trifluoromethyl)pyridine, molecular formula is C7H5F3N2O2, 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 solution of 6.0 g (23.29 mM) of 4-methyl-5-nitro-2-trifluoromethylpyridine (Preparation 4) in 14.8 mL (109.45 mM) diethyl oxalate was prepared. 8.65 g (56.8 mM) of DBU were added and the mixture was stirred for 4 hours at room temperature. The medium was concentrated under reduced pressure and the residue was then dissolved in 120 mL of acetic acid. This mixture was brought to 60 C. and 2.60 g (46.6 mM) of iron were added. The medium was heated at 70 C. overnight. The medium was diluted with water and the precipitate formed was filtered off and washed three times with water. The solid was dissolved in ethyl acetate, and the solution was filtered. The filtrate obtained was concentrated under reduced pressure. The title product was obtained in the form of a brown solid (5.70 g, yield=95%). m.p.=142 C

According to the analysis of related databases, 944317-53-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laboratoires Fournier SA; US2012/302560; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16179-97-8, 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. 16179-97-8, name is 2-(Pyridin-2-yl)acetic acid hydrochloride, molecular formula is C7H8ClNO2, 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.

S2 was prepared analogously to a published procedure.13 2.00 g S1 (11.5 mmol, 1.00 equiv.) and 14 mL MeOH were added to a round-bottom flask. The solution was cooled to 0 C, and 2.90 mL TMSCl (23.0 mmol, 2.00 equiv.) were added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The solvent was then removed in vacuo, ant the remaining solid was treated slowly with sat. aq. NaHCO3 (40 mL). The aqueous solution was extracted with CH2Cl2 (4 x 40 mL), and the combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed in vacuo. The crude product (S2) was isolated as a clear oil (1.73 g, 11.47 mmol, quant.). The spectral data of the compound were compared with the published ones.13

According to the analysis of related databases, 16179-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Podhajsky, Susanne M.; Iwai, Yasumasa; Cook-Sneathen, Amanda; Sigman, Matthew S.; Tetrahedron; vol. 67; 24; (2011); p. 4435 – 4441;,
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. 116026-93-8, name is tert-Butyl (3-formylpyridin-4-yl)carbamate, molecular formula is C11H14N2O3, 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. Quality Control of tert-Butyl (3-formylpyridin-4-yl)carbamate

Preparation 56 : 2-tert-Butoxycarbonylamino-3-(4-tert-butoxycarbonylaminopyridin-3-yl) acrylic acid methyl ester; To a solution of (+/-)-Boc-alpha-phosphonoglycine trimethyl ester (1.5Og, 5.05mmol) in dry THF (2OmL) at -780C was added 1,1,3,3-tetramethylguanidine (0.6OmL, 4.78mmol) and the mixture was stirred in the cold for 20min. A solution of 4-[N-(tert-butyloxycarbonyl)amino]-3- pyridinecarboxaldehyde (Preparation 55, 1.Og, 4.50mmol) in dry THF (1OmL) was added slowly and the resulting mixture allowed to warm up to rt and stirred for additional 12h before being poured into water (20OmL). Extraction with EtOAc (3x75mL) and washing of the combined extracts with brine (5OmL) gave after drying (MgSO4) and concentration in vacuo an oily residue. Purification of the residue by flash chromatography on silica gel (eluent: toluene / acetone : 2 /1) gave the title compound as colourless oil. delta? (CDCl3): 1.31 (9H, s), 1.53 (9H, s), 3.91 (3H, s), 6.61, 6.76 (2H, 2 xbr s), 7.05 (IH, s), 8.06 (IH, d), 8.37-8.39 (2H, m); m/z (ES+) = 394.13 [M+H]+; RT = 2.81 min.

With the rapid development of chemical substances, we look forward to future research findings about 116026-93-8.

Reference:
Patent; PROSIDION LIMITED; WO2006/59164; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 71690-05-6, 2,3-Dichloro-5-formylpyridine, 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: C6H3Cl2NO, blongs to pyridine-derivatives compound. Formula: C6H3Cl2NO

To a stirred slurry of methyltriphenylphosphonium bromide (10.0 g) in toluene (200 mL) at 0 C. was added potassium t-butoxide (3.07 g) portionwise to produce a yellow slurry. After 1 hr, the reaction mixture was cooled to -20 C. and 4 (4.0 grams, 22.72 mmol) dissolved in tetrahydrofuran (6 mL) was added dropwise to produce a purple colored slurry. The reaction mixture was heated to 0 C. and stirred for an additional 1 hr. Then the reaction mixture was treated with saturated aqueous brine (150 mL) and diluted with ethyl acetate (200 mL). The resulting organic portion was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting product was chromatographed by silica gel chromatography column eluting with a gradient of ethyl acetate (0%-10%)/hexanes to provide 2.77 g of 1 (70% yield). 1H NMR (400 MHz, CDCl3) delta 8:30 (1H, d, J=2.19 Hz), 7.80 (1H, d, J=2.19 Hz), 6.63 (1H, dd, J=10.96, 17.80 Hz), 5.86 (1H, d, J=17.80 Hz), 5.45 (1H, d, J=10.96 Hz). LC/MS (M+1): 174.

The synthetic route of 71690-05-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tafesse, Laykea; US2010/120862; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 66521-66-2, 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. 66521-66-2, name is 4-(Pyridin-3-yl)pyrimidin-2-amine, molecular formula is C9H8N4, 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 solution under nitrogen gas of 2-(3-methyl-4-bromobenzylamino)-3-cyano-4-(4-tert- butylaminopiperidin-1-yl)quinoline (190 mg, 0.376 mmol) in toluene (10 ml) was added 4-(pyridin- 3-yl)pyrimidin-2-amine (71 mg, 0.413 mmol) and t-BuONa (72 mg, 0.752 mmol). The resulting mixture was degassed 10 min with Argon gas, then Xantphos (21 mg, 0.0376 mmol) and Pd2(dba)3 (34 mg, 0.0376 mmol) were added and the reaction mixture was stirred at 100 °C for 1 h. The reaction mixture was then cooled to room temperature, filtered and concentrated under reduced pressure. The residue was partitioned between brine and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give yellow oil. The crude compound which upon purification by flash chromatography using (silica-gel: 100-200 mesh, MeOH?CHCl3; 0:100? 20:80) gave 60 mg (yield 26percent) of an pale-yellow solid corresponding to 2-[4-(4-(pyridin-3- yl)pyrimidin-2-ylamino)-3-methylbenzylamino]-3-cyano-4-(4-tert-butylaminopiperidin-1- yl)quinoline. Mass:(ES+) C36H39N9 required 597; found 598 [M+H], HPLC/MS method 6

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 66521-66-2, 4-(Pyridin-3-yl)pyrimidin-2-amine.

Reference:
Patent; GENOSCIENCE PHARMA; BRUN, Sonia; BERET, Antoine; BASSISSI, Firas; HALFON, Philippe; COURCAMBECK, Jerome; (275 pag.)WO2017/191599; (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 131084-55-4, name is 5-Chloro-1H-pyrrolo[2,3-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H5ClN2

5-Chloro-lH-pyrrolo[2,3-c]pyridine (400.0 mg, 2.614 mmol, 1.0 eq) was dissolved in DMF (20.0 mL). After cooling to 0 C, NIS (882 mg, 3.922 mmol, 1.5 eq) was added and the resulting mixture was stirred at rt for 18 h, then concentrated in vacuo. The resulting residue was purified by column chromatography to provide 5-chloro-3-iodo-lH- pyrrolo[2,3-c]pyridine (725 mg, ca 100%).

With the rapid development of chemical substances, we look forward to future research findings about 131084-55-4.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1020253-15-9, 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.1020253-15-9, name is 4-Bromo-2-chloro-5-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.

Step 105.2: 4-Bromo-5-methoxy-1-methyl-1 H-pyridin-2-one A solution of 4-bromo-2-chloro-5-methoxypyridine (1 g, 4.5 mmol) in dimethyl sulfate (1.9 mL, 19.5 mmol) was stirred at 120C for 16 h in a sealed tube. After cooling, acetonitrile and a saturated aqueous NaHC03 solution were added and the mixture was stirred at rt over week-end. DCM was added and extracted. The organic layer was dried (Na2S04), filtered and concentrated to give the title compound. tR: 0.57 min (LC-MS 2); ESI-MS: 218.0/220.0 [M+H]+ (LC-MS 2).

The chemical industry reduces the impact on the environment during synthesis 1020253-15-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; LIAO, Lv; MAH, Robert; MAO, Liang; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/111105; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem