Day: April 7, 2022

Application of 597532-36-0, 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 597532-36-0, name is Ethyl 6-(trifluoromethyl)nicotinate. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of ethyl 6-(trifluoromethyl)nicotinate (2.2 g, 10 mmol), Pd/C ( 10 wt.%, 100 mg) and platinum(IV)oxide (150 mg, 0.661 mmol) in acetic acid (30 mL) was stirred in a steel bomb under hydrogen atmosphere (200 psi) at 25 C for 24 hrs. The reaction mixture was filtered through a pad of celites and washed with MeOH (150 mL). The filtrate was concentrated under reduced pressure providing crude ethyl 6- (trifluoromethyl)piperidine-3-carboxylate (776 mg; mixture of cis and trans isomers) as a colorless oil, which was directly used in the next step without further purification.LCMS (m/z): 226.1 [M+H]+; Rt = 0.36 min.

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 597532-36-0, Ethyl 6-(trifluoromethyl)nicotinate.

Reference:
Patent; NOVARTIS AG; PFISTER, Keith B; SENDZIK, Martin; WO2011/26917; (2011); 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.57883-25-7, name is 3-Bromo-2-ethoxypyridine, molecular formula is C7H8BrNO, molecular weight is 202.05, as common compound, the synthetic route is as follows.COA of Formula: C7H8BrNO

To a solution of 465 3-bromo-2-ethoxy-pyridine (350 mg, 1.7 mmol) in NMP (2 mL) was added 423 Zn(CN)2 (244 mg, 2.1 mmol) and Pd(dppf)Cl2 (127 mg, 0.17 mmol). The mixture was degassed with N2 and heated at 140 C. under microwave irradiation for 1 hour. The mixture was cooled to room temperature and filtered through celite. The filtered cake was washed with ethyl acetate (30 mL). The filtrate was washed with water (20 mL×2) and brine (20 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (0%?20% 56 ethyl acetate in 57 petroleum ether) to give 467 2-ethoxynicotinonitrile.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57883-25-7, 3-Bromo-2-ethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Kehler, Jan; Rasmussen, Lars Kyhn; Clementson, Carl Martin Sebastian; Marigo, Mauro; (154 pag.)US2019/194189; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 33252-28-7, 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 33252-28-7 as follows.

To a solution of potassium tert-butoxide (0.891 g, 7.94 mmol) in tetrahydrofuran (40 mL) at 0 0C was isopropanol (0.608 mL, 7.94 mmol) added. 6-chloronicotinonitrile (1.0 g, 7.22 mmol) was added after stirrng for 5 min and the reaction mixture was allowed to reach ambient temperature. The reaction mixture was concentrated in vacuo, water (50 mL) was added and the resulting mixture extracted with ethyl acetate (3x 50 mL). The crude was suspended in 4M sodium hydroxide (30 mL) and heated to reflux over night. The reaction mixture was concentrated in vacuo and IM hydrochloric acid was added until an acidic pH was reached. The formed precipitate was collected by filtration and washed with water to yield 1.14O g (85 %) of the title compound; 1R NMR (400 MHz, DMSO-J6) delta ppm 12.99 (s, 1 H), 8.70 (d, 1 H), 8.10 (dd, 1 H), 6.82 (d, 1 H), 5.21 – 5.40 (m, 1 H), 1.31 (d, 6 H); MS (ESI) m/z 182 [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,33252-28-7, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2008/130320; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 175204-80-5, 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. 175204-80-5, name is 3-Amino-4-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

Example 1 (2R, 5S)-4- (8-Cyano-quinolin-5-yl)-2, 5-dimethyl-piperazine-l-carboxylic acid (4- trifluoromethyl-pyridin-3-yl)-amide A. Preparation of (2R)-2-Benzylamino-propionic acid methyl ester (1A) Benzaldehyde (20 ml, 0.2 mol) and TEA (25 ml, 0.18 mol) were added to D- alanine methyl ester hydrochloride (25g, 0.18 mol) in THF (300 ml) at RT. After 48 hrs, the reaction mixture was filtered through celite (the mixture was washed with 150 ml THF) and concentrated. The reaction crude was dissolved in MeOH (400 ml) and cooled to 0C. Sodium borohydride (7.5 g, 0.2 mol) was slowly added in portions, and the reaction mixture was stirred at 0C for 3 hrs. The reaction was quenched with 1N NaOH (125 ml), concentrated and extracted with DCM (4 x 200 ml), dried over Na2S04, and concentrated to isolate 1A as a clear, off-white oil (31.7 g, 91%). [M+H] + = 194. B. Preparation of (3S, 6R)-l-Benzyl-3, 6-dimethyl-piperazine-2, 5-dione (1B) (2R) -2-Benzylamino-propionic acid methyl ester (1A) (1.0 g, 5.2 mmol) and N-tert-butoxycarbonyl-L-alanine (0.98 g, 5.2 mmol) were added to DCC (1.07 g, 5.2 mmol) in DCM (55 ml) at 0C. After addition, the reaction mixture was warmed to RT, stirred for 24 hrs, filtered through celite (with 2 x 50 ml diethyl ether wash), and concentrated. The reaction mixture was dissolved in DCM (30 ml), cooled to 0C, and TFA (5 ml) was added. After 10 min, the reaction mixture was warmed to RT and stirred for 3 hrs. The reaction was quenched by slow addition of saturated NaHCO3 (100 ml), and extracted with DCM (3 x 75 ml), dried over Na2S04 and purified by silica gel flash chromatography (EtOAc) to isolate 1B as a clear oil (0.68 g, 57%). [M+H] + = 233.14. C. Preparation of (2S, 5R)-1-Benzyl-2, 5-dimethyl-piperazine (1C) LiAlH4 (60 mmol, 60 ml of 1.0 M solution in THF) was added to (3S, 6R)-1- benzyl-3,6-dimethyl-piperazine-2, 5-dione (1B) (3.48 g, 15 mmol) in THF (100 ml) at 0C. After addition, the reaction mixture was heated at 70 C for 24 hrs. The reaction was cooled to 0 C and quenched by slow addition of H20 (3.5 ml), 1 N NaOH (3.5 ml) and H2O (3.5 ml). The reaction mixture was filtered through celite and washed with THF (100 ml) and EtOAc (100 ml), dried over Na2S04, concentrated and purified by flash chromatography (15% MeOH/CHCl3 with 1% TEA) to isolate 1C as a clear oil (2.43 g, 79%). [M+H] + = 205.16. D. Preparation of 5-Bromo-quinoline-8-carbonitrile (1D) NaN02 (345 mg, 5.0 mmol) in H20 (2.0 ml) was added to 5-amino-quinoline- 8-carbonitrile (770 mg, 4.6 mmol) in 48% HBr (aqueous, 2.0 ml) at 0 C. After 30 minutes, CuBr (522 mg, 3.6 mmol) in 48% HBr (aqueous, 1.5 ml) is added. After addition, the reaction mixture was heated at 100 C for 1 hr and cooled to RT. The reaction was neutralized to pH 8 with 1N NaOH and extracted with EtOAc (2X100 ml). The pooled organic phase was washed with H20 (100 ml), saturated NH40H (100 ml), dried over Na2S04, concentrated, and purified by silica gel flash chromatography (stepwise gradient: DCM to 2% EtOAc/DCM) to isolate compound 1D as a white solid (550 mg, 51%). [M+H] +=235. 09. E. Preparation of (2S, 5R)-5- (4-Benzyl-2, 5-dimethyl-piperazin-1-yl)- quinoline-8-carbonitrile (lE) In a microwave compatible reaction flask, (+)-(S)-N, N-Dimethyl-1-[(R)-2- (diphenylphosphino) ferrocenyl] ethylamin (15.4 mg, 0.035 mmol), compound 1D (82 mg, 0.35 mmol), and compound 1C (86 mg, 0.42 mmol) were dissolved in toluene (3.5 ml) and degassed with N2 for 5 min. Tris (dibenzylideneacetone) dipalladium (0) (32 mg, 0.035 mmol), sodium tert-butoxide (50 mg, 0.52 mmol) were added, and the reaction mixture was degassed with N2 for 5 additional min. The reaction mixture was heated at 120 C under high absorption microwave for 40 minutes, diluted with EtOAc (2 ml), filtered, concentrated, and purified using prep HPLC to isolate compound 1E as a TFA salt. Compound 1E was diluted in saturated aqueous NaHCO3 (10 ml) and extracted with DCM (2X10ml), and concentrated to isolate 1E as yellow film (17.8 mg, 14%). [M+H] + = 357. 48. F. Preparation of (2S, 5R)- 5- (2, 5-Dimethyl-piperazin-1-yl)-quinoline-8- carbonitrile (1F) 1-Chloroethyl chloroformate (0.054 ml, 0.5 mmol) was added to compound 1E (18 mg, 0.05 mmol) in dichloroethane (1 ml). The reaction mixture was heated at 85 C for 18 hrs, concentrated and dissolved in MeOH and heated at 65 C for additional 24 hrs. The reaction mixture was diluted in saturated aqueous NaHCO3 (10 ml) and extracted with DCM (2x10ml), dried over Na2S04, concentrated and purified by silica gel flash chromatography (10% MeOH/CHCl3 with 1% TEA) to isolate compound IF as yellow film (4.5 mg, 34%). [M+H] + = 267.36 G. Preparation of (2R, 5S)-4- (8-Cyano-quinolin-5-yl)-2, 5-dimethyl- piperazine-1-carboxylic acid (4-trifluoromethyl-pyridin-3-yl) -amide) (1) 4-Trifluoromethyl-pyridin-3-ylamine (4 mg, 0.025 mmol) and TEA (0.0035 ml, 0.025 mmol) in DCM (0.5 ml) were added to triphosgene (2.5 mg, 0.0085 mmol) in DCM (0.25 ml) at 0C. After 5 min the reaction mixture was …

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175204-80-5, 3-Amino-4-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2005/40136; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 70411-83-5, name is 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 70411-83-5

1- Methyl-2-oxo-1,2-dihydropyridine-4-carbonitrile (302 mg), it was heated under reflux for 3 hours a mixture of 50% hydroxylamine aqueous solution (160 muL) and ethanol (2.0 mL). The reaction mixture wasconcentrated under reduced pressure to give the title compound (366 mg) as a colorless solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 70411-83-5, 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbonitrile.

Reference:
Patent; TAISHO PHARMACEUTICAL COMPANY LIMITED; KONISHI, KAZUHIDE; KANUMA, KOSUKE; NAKAMURA, TOSHIO; AMADA, HIDEAKI; YAMAMOTO, SHUJI; KASHIWA, SHUHEI; MASUDA, SEIJI; OKADA, KUMIKO; KAWAMOTO, HIROSHI; (74 pag.)JP2015/78127; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 800401-70-1 ,Some common heterocyclic compound, 800401-70-1, molecular formula is C10H9BrN2O2, 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.

PdCl2 (PPh3) 2 (0.026g, 0.037mmol) and Cu (I) I (0.007g, 0. 037MMOL) were added sequentially to 5-BROMO-LH-PYRROLO [2,3-c] pyridine-2-carboxylic acid ethyl ester (Preparation 26, 0. 100G, 0.370mmol) under an argon atmosphere. 1,4-Dioxane (7mL, anhydrous) followed by DIISOPROPYLAMINE (0.063mL, 0. 45MMOL) were added and the stirred mixture was purged with argon for 5min. Trimethylsilylacetylene (0.064mL, 0. 45MMOL) was added dropwise and the resulting mixture stirred at rt for 24h. The reaction mixture was partitioned between water (50ML) and ethyl acetate (LOOML) and the layers separated. The aqueous phase was extracted with ethyl acetate (3X30ML). The combined organics were washed with brine (50ML), dried (MGS04), filtered and concentrated in vacuo. The residue was dissolved in the minimum amount of dichloromethane and loaded onto a silica column. Purification via flash column chromatography (SI02, dichloromethane then 25% ethyl acetate/ isohexane) gave a pale yellow solid. 8H (CDCl3): 0.28 (9H, s), 1.43 (3H, t), 4.45 (2H, q), 7. 18 (1H, s), 7.83 (1H, s), 8.86 (1H, s), 9.21 (1H, br s).

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. 800401-70-1, Ethyl 5-bromo-1H-pyrrolo-[2,3-c]-pyridine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2004/104001; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 131747-62-1, 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. 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde. A new synthetic method of this compound is introduced below.

25 mL of anhydrous THF was placed under nitrogen and cooled to -78 C. 2.2 ml (5.5 mmol) of a 2.5 M solution of n-butyl lithium in hexanes were added. To the resulting solution was slowly added 0.7 mL (1.4 g, 5.8 mmol) of 1,3-dibromobenzene. Upon complete addition the resulting solution was stirred at -78 C. for 90 min. 1.00 g (5.71 mmol) of 3-trifluoromethyl-pyridine-2-carbaldehyde was added rapidly. The dark solution was warmed to -20 C. and stirred for 20 min at that temperature. The resulting mixture was distributed between 10% aqueous citric acid and dichloromethane. The phases were separated and the aqueous layer extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and the solvent completely evaporated. The resulting residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford 1.053 g (3.171 mmol, 58%) of (3-bromo-phenyl)-(3-trifluoromethyl-pyridin-2-yl)-methanol as a yellow oil. 1H NMR (500 MHz, DMSO-d6) delta 8.84 (m, 1H), 8.18 (dd, 1H), 7.63 (m, 1H), 7.53 (dd, 1H), 7.42 (m, 1H), 7.26-7.24 (m, 2H), 6.31 (d, 1H), 6.02 (d, 1H),; MS: m/z 332.0+334.0 (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,131747-62-1, its application will become more common.

Reference:
Patent; SGX Pharmaceuticals, Inc.; US2008/261921; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1256805-54-5, 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. 1256805-54-5, name is 6-Chloro-4-methoxypyridin-3-amine. A new synthetic method of this compound is introduced below.

Trimethylaluminum (7.6 mL, 2.0 M in toluene, 15 mmol) was added slowly to a 0 C. mixture of 6-chloro-4-methoxypyridin-3-amine (2.4 g, 15 mmol) and propionitrile (1.16 mL, 16.1 mmol). The flask was removed from the ice bath, allowed to warm to rt over 5 min, then was stirred at 105 C. for 17 hours. The mixture was cooled to 0 C. and THF (15 mL) was added very slowly followed by water (1 mL), 15 wt % aqueous NaOH (1 mL) and water (3 mL), stirring for 10 min after each addition. The resulting mixture was allowed to warm to rt over 30 min with stirring, then Celite was added, and the mixture stirred an additional 30 min. The mixture was then filtered through Celite with THF and concentrated. The residue was diluted with water and the pH adjusted to pH 1-2 by the addition of 1 N aqueous HCl. The solution was then washed twice with EtOAc and the aqueous layer pH adjusted to pH 10-11 by the addition of 1 N aqueous NaOH. The aqueous solution was then extracted four times with DCM, the organic layers combined, dried with anhydrous Na2SO4, filtered and concentrated to provide the title compound, which was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1256805-54-5, 6-Chloro-4-methoxypyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; Martin, Connor L.; Fennema, Elizabeth G.; Kummer, David A.; Nishimura, Rachel T.; Tanis, Virginia M.; Woods, Craig R.; Fourie, Anne M.; Xue, Xiaohua; (120 pag.)US2019/382354; (2019); 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. 34206-49-0, name is 5-Bromopyridine-2,3-diol, the common compound, a new synthetic route is introduced below. COA of Formula: C5H4BrNO2

To a solution of 5-bromopyridine-2,3-diol (10 g, 53.19 mmol, 1 eq.) in DMF (250 mL) atroom temperature was added K2C03 (21 g, 159.57 mmol, 3 eq.) followed by 1,2-dibromoethane(5.5 mL, 63.82 mmol, 1.2 eq.) dropwise. The resulting mixture was stirred at 100C overnight.Progress of reaction was monitored by TLC. After the completion, reaction mixture was cooledto room temperature, diluted with ice cold water (300 mL) and extracted with DCM (3 x300 mL).Combined organic layer was washed with brine and dried over anhydrous sodium sulphate.Removal of solvent under reduced pressure afforded crude was purified by Combi-Flash on silica gel using methanol-dichloromethane (0-50 %) as eluents to afford 7-bromo-2,3-dihydro- [1,4]dioxino[2,3-b]pyridine (2.9 g, 25.26%).LCMS: 215 [M+1]

The synthetic route of 34206-49-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURANSA INC.; PROTTER, Andrew, Asher; GREEN, Michael, John; CHANG, Hak, Jin; PHAM, Son, Minh; CHAKRAVARTY, Sarvajit; LUEDTKE, Gregory, R.; (254 pag.)WO2019/103897; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1452-94-4, 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 1452-94-4, name is Ethyl 2-chloronicotinate. This compound has unique chemical properties. The synthetic route is as follows.

To ethyl 2-chloronicotinate (15.0 g, 81 mmol) in anhydrous N, N-dimethylacetamide (75 ml) was added zinc cyanide (5.71 g, 48.6 mmol), Pd2 (dba) 3 (742 mg, 0.81 mmol), zinc (636 mg, 9.72 mmol), and 1, 1’BIS (diphenylphosphino) ferrocene (898 mg, 1.62 mmol), and the resulting mixture heated at 120 C for 1 hour. The mixture was cooled to room temperature and partitioned between water (300 ml) and diethyl ether (150 ml), the mixture was filtered through Celiez and the phases separated. The aqueous phase was further extracted with diethyl ether (2 x 100 ml), the combined diethyl ether layers washed with saturated NACI, dried over NA2SO4, FILTERED and evaporated to give the title compound (14.26 g, 100%).

According to the analysis of related databases, 1452-94-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Limited; WO2004/46133; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem