Category: pyridine-derivatives

Reference of 1659-31-0, 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. 1659-31-0, name is Dipyridin-2-yl carbonate. A new synthetic method of this compound is introduced below.

Under nitrogen atmosphere, to a stirred mixture of (4-cyclohexylphenyl)-methanol (0.3 g, 1.58 mmol) in dry CH2C12 (2 mL), DMAP (0.019 g, 0.16 mmol) and di-2-pyridyl- carbonate (0.41 1 g, 1.90 mmol) were added. The reaction mixture was left to react at rt for 15 h, then diluted with CH2C12 and washed first with a saturated NH4C1 solution (3.0 mL) and subsequently with a saturated NaHC03 solution (3X3 mL). The organic fraction was dried over Na2S04, filtered and concentrated to dryness to afford a colorless oil (0.464 g, 95%), as a mixture (ratio 1.8: 1) of (4-cyclohexylphenyl)-methyl-2-pyridyl carbonate and (4- cyclohexylphenyl)-methy 1-2 -oxopyridine-1 -carboxylate. The mixture of isomers was not separated and used in the next step without any further purification. MS (ESI) m/z 350 [M- K]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1659-31-0, Dipyridin-2-yl carbonate, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; IIT – ISTITUTO ITALIANO DI TECNOLOGIA; UNIVERSITY DEGLI STUDI DI URBINO; UNIVERSITA DEGLI STUDI DI PARMA; PIOMELLI, Daniele; BANDIERA, Tiziano; MOR, Marco; TARZIA, Giorgio; BERTOZZI, Fabio; PONZANO, Stefano; WO2013/78430; (2013); 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 1211540-79-2, name is 2,3-Dihydro-1H-pyrrolo[3,2-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C7H8N2

To a solution of 2,3-dihydro-1 H-pyrrolo[3,2-b]pyridine (9.05 g, 75.3 mmol) and dichloropyrimidine (12.3 g, 75.3 mmol) in te/t-butanol (90 mL) and toluene (90 mL) was added cesium carbonate (37.6g). The mixture was degassed with a stream of nitrogen gas. Bis(triphenylphosphine)palladium(ll) dichloride (1.59 g) was added and the mixture was again degassed with nitrogen for several minutes. The resulting mixture was heated at reflux (115 degrees Celsius) for 18 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and the mixture was filtered through diatomaceous earth. The filtrate was concentrated in vacuo to an oil. This oil was dissolved in 2-methyl tetrahydrofuran (400 mL) and 300 mL of 1 N aqueous hydrochloric acid was added. The aqueous layer was separated and extracted twice with 2-methyl tetrahydrofuran. The combined organic extracts were washed with water. The combined aqueous layers were cooled in an ice bath and triethylamine was added slowly until the pH was adjusted to 8 to 9. A precipitate formed and these solids were collected by filtration. The aqueous filtrate was extracted twice with 2-methyl tetrahydrofuran. These combined organic extracts were washed with brine, dried over sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was combined with the previously collected solids, dissolved in 2-methyl tetrahydrofuran and concentrated in vacuo. The reside was purified by flash chromatography using 330 g of silica gel, eluting with a gradient mixture of heptane and ethyl acetate (50 to 100% over 30 min and then 100% ethyl acetate for 30 min) to give 1-(6-chloro-5-methylpyrimidin-4-yl)-2,3- dihydro-1 H-pyrrolo[3,2-b]pyridine as an off-white solid (25.5 g). 1H NMR (400 MHz, deuterochloroform) delta 2.27 (s, 3 H) 3.29 (t, J=8.39 Hz, 2 H) 4.18 (t, J=8.39 Hz, 2 H) 7.03 (dd, J=8.10, 4.98 Hz, 1 H) 7.20 (dd, J=8.10, 1.27 Hz, 1 H) 8.07 (dd, J=5.08, 1.37 Hz, 1 H) 8.47 (s, 1 H)

With the rapid development of chemical substances, we look forward to future research findings about 1211540-79-2.

Reference:
Patent; PFIZER INC.; DAROUT, Etzer; DENINNO, Michael, Paul; FUTATSUGI, Kentaro; GUIMARAES, Cristiano, Ruch, Werneck; LEFKER, Bruce, Allen; MASCITTI, Vincent; MCCLURE, Kim, Francis; MUNCHHOF, Michael, John; ROBINSON, Ralph, Pelton, Jr.; WO2010/128414; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72990-37-5 ,Some common heterocyclic compound, 72990-37-5, molecular formula is C6H4ClNO, 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.

Reference Production Example 4 To a mixture of 1.53 g of 3-chloroisonicotinaldehyde and 5 ml of ethanol was gradually added 0.40 g of sodium borohydride under ice-cooling, and the mixture was stirred under ice-cooling for 1 hour, and subsequently at room temperature for 1 hour. Saturated brine was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layers were combined and dried over magnesium sulfate. The resulting mixture was concentrated under reduced pressure to obtain 1.40 g of (3-chloropyridin-4-yl)methanol. 1H-NMR (CDCl3) delta: 8.54-8.49 (m, 2H), 7.55-7.51 (m, 1H), 4.83 (d, J=4.4 Hz, 2H), 2.34-2.29 (br m, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,72990-37-5, its application will become more common.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; Iwakoshi, Mitsuhiko; Takyo, Hayato; US2013/90353; (2013); 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

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

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

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

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