Tag: M.W:100-200

Reference of 72587-18-9, 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. 72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, 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.

6-Bromo-3-(ethylsulphanyl)pyridine-2-carboxylic acid (3 g, 11.5 mmol) was dissolved in 60 ml of dichloromethane and cooled to 0 C. With stirring, oxalyl chloride (14.5 g, 115 mmol) and one drop of dimethylformamide were added, then the mixture was stirred at room temperature for 30 min. After removing the solvent, the crude product 6-bromo-3-(ethylsulphanyl)pyridine-2-carbonyl chloride was further reacted directly. 2-Chloro-5-(trifluoromethyl)pyridin-3-amine (1.05 g, 5.38 mmol) was added at 0 C. to a suspension of sodium hydride (60% in mineral oil, 258 mg, 6.46 mmol) in tetrahydrofuran. The mixture was stirred for 30 min, then 6-bromo-3-(ethylsulphanyl)pyridine-2-carbonyl chloride (3 g, 10.75 mmol) was added in portions. After stirring for 12 h, the reaction was ended by adding 10 ml of ice-water. The product was isolated in the form of a precipitate by filtration. log P (neutral): 5.27; MH+: 442; 1H-NMR (400 MHz, D6-DMSO) delta ppm: 10.57 (s, 1H); 8.91 (s, 1H), 8.70 (s, 1H), 7.95-7.87 (m, 2H), 3.05-3.00 (m, 2H), 1.30-1.27 (m, 3H).

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 72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHSAFT; FISCHER, RUEDIGER; WILCKE, DAVID; KAUSCH-BUSIES, NINA; HAGER, DOMINIK; ILG, KERSTIN; HOFFMEISTER, LAURA; WILLOT, MATTHIEU; PORTZ, DANIELA; GOERGENS, ULRICH; TURBERG, ANDREAS; (161 pag.)US2018/271099; (2018); 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

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

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

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

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 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

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

Synthetic Route of 1254473-66-9, 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. 1254473-66-9, name is 1-(3,5-Dichloropyridin-4-yl)ethanol, molecular formula is C7H7Cl2NO, 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.

Separate the mixture of stereoisomers obtained in Preparation 1 on a CHIRALPAK AD-H column eluting with 90% heptanes/10% ethanol. Peak 2 is the desired enantiomer. To establish the absolute configuration dissolve a sample of the product in CDCl3 (final concentration 100 mg/mL). Obtain the vibrational circular dichroism (VCD) and infra red (IR) spectra with a resolution of 4 cm-1 using a ChiralIR FT VCD spectrometer (BioTools Inc) with an IR cell equipped with BaF2 windows and a path length of 100 mm. Collect the VCD and IR for 6 hours with 150 muL of the sample. Present the data without smoothing or further data processing. Obtain vibrational frequencies and absorption and VCD intensities by optimizing the lowest energy conformer by Gaussian at the B3PW91/6-31G** level on a Linux cluster, and simulate the corresponding spectra using a Lorentzian bandwidth of 6 cm-1 vibrational circular dichroism. The above analysis shows the product to be the S-isomer. Yield: 84.37 g (27%). MS (ES) m/z 192 [M+1]+.

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 1254473-66-9, 1-(3,5-Dichloropyridin-4-yl)ethanol.

Reference:
Patent; ELI LILLY AND COMPANY; US2012/83511; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 274-76-0 ,Some common heterocyclic compound, 274-76-0, molecular formula is C7H6N2, 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 DMF (120 mL, 1.55 mol) at 2 C, freshly distilled phosphorus oxychloride (61 mL, 0.65 mol) was slowly added. The temperature was allowed to rise gradually to room temperature. The solution was cooled again to 2 C and a solution of imidazo[1,2-a]-pyridine 1 (10 g, 0.085 mol) in DMF (60 mL) was added dropwise. The mixture was warmed to 105 C, whereupon the temperature rose to 140 C. The oil bath was removed until the temperature stabilized at 120 C. The reaction mixture was heated for 45 min at 120 C and 2.5 h at 85 C, then cooled and poured into 5% HCl (600 mL) ice-cooled and brought to pH 9 using 20% NaOH. The resulting solution was extracted with CH2Cl2 (1200 mL) overnight. Then the organic layer was separated and dried over MgSO4, the solvent removed under reduced pressure, the crude product washed with water (5 × 15 mL) and again dried, providing the pure product 3.49 g (31%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,274-76-0, its application will become more common.

Reference:
Article; B?aewska, Katarzyna M.; Ni, Feng; Haiges, Ralf; Kashemirov, Boris A.; Coxon, Fraser P.; Stewart, Charlotte A.; Baron, Rudi; Rogers, Michael J.; Seabra, Miguel C.; Ebetino, Frank H.; McKenna, Charles E.; European Journal of Medicinal Chemistry; vol. 46; 10; (2011); p. 4820 – 4826;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem