Month: April 2022

Application of 75291-85-9, 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.75291-85-9, name is 5-Bromo-2-chloronicotinamide, molecular formula is C6H4BrClN2O, molecular weight is 235.47, as common compound, the synthetic route is as follows.

B) 2-(4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)nicotinamide, bis(trifluoroacetic acid) salt; 4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorobenzenamine (51.7 mg, 0.21 mmol) and 5-bromo-2-chloronicotinamide (50 mg, 0.21 mmol) were suspended in 3:1 isopropanol-NMP (2.1 mL). 4N HCl in 1,4-dioxane (0.21 mL, 0.84 mmol) was added and the reaction was heated to 100 C. for 240 h. The isopropanol was removed by rotary evaporation and the resulting residue was partitioned between 5% aq. NaHCO3 solution (10 mL) and EtOAc (10 mL). The organic layer was separated and the aqueous layer was extracted EtOAc (2×10 mL). The combined organic layers were washed with 10% LiCl (20 mL), dried (MgSO4) and concentrated. The crude product was purified by preparative (RP) HPLC chromatography (YMC S5 ODS, 30×75 mm, 10 minute gradient from 33% to 90% aqueous methanol with 0.1% TFA, 40 mL/min). The fractions containing the desired product were combined and concentrated to afford the desired product as a tan powder (10.1 mg, >98% HPLC purity). 1H NMR (DMSO-d6) delta 12.00 (s, 1H), 11.38 (s, 1H), 8.44 (s, 1H), 8.44 (dd, 1H, J=23.91, 2.03 Hz), 8.13 (d, 1H, J=5.59 Hz), 8.06 (d, 1H, J=13.23 Hz), 7.92 (s, 1H), 7.42 (s, 1H), 7.29-7.38 (m, 2H), 6.46 (d, 1H, J=5.59 Hz), 6.32 (s, 1H); MS(ESI+) m/z 442.1 (M+H)+.

Statistics shows that 75291-85-9 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-chloronicotinamide.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/78140; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1221171-88-5, 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.1221171-88-5, name is 5-(Trifluoromethoxy)pyridin-2-amine, molecular formula is C6H5F3N2O, molecular weight is 178.11, as common compound, the synthetic route is as follows.

Int-82 (200 mg, 1.12 mmol) was dissolved in DCM (10 mL) and a solution of Nbromosuccinimide (200 mg, 1.12 mmol) in DCM (5 mL) was added dropwise. The mixture was stined at rt for 16 h. The solvent was removed under reduced pressure and the residue was purified by colunm chromatography on silica gel using a mixture of petroleum ether and EtOAc (2:1) as eluent to give 3-bromo-5-(trifluoromethoxy)pyridin-2-amine (int-83) (200 mg, 69%) as a yellow solid. MS (ESI): mlz 257.9 [M+Hj.

Statistics shows that 1221171-88-5 is playing an increasingly important role. we look forward to future research findings about 5-(Trifluoromethoxy)pyridin-2-amine.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena V.; HOLZWARTH, Michael S.; (160 pag.)WO2018/81612; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1226878-98-3, Adding some certain compound to certain chemical reactions, such as: 1226878-98-3, name is 2-Chloro-5-iodo-4-methoxypyridine,molecular formula is C6H5ClINO, 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 1226878-98-3.

General procedure: The appropriate 5-iodo-2-chloropyridine Intermediate I-8, or I-9 (1 eq) was dissolved in acetonitrile (7 ml. solvent per 1 mmol of compound). 1 -Methyl-4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole (1 eq), tetrakis – (triphenylphosphine)palladium(O) (5 mol%) and sodium carbonate (1 .5 eq) were added and the mixture was heated in a microwave reactor at 100C for 30 minutes (Intermediate I-8) or 15 minutes (Intermediate I-9). The reaction mixture was concentrated in vacuo onto silica gel. Gradient chromatography (1-5% MeOH:CH2CI over 15 column volume and 5-10% over 8 column volume) gave the required 5-substituted product.

According to the analysis of related databases, 1226878-98-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; COLLINS, Ian; LAINCHBURY, Michael; MATTHEWS, Thomas Peter; READER, John Charles; WO2013/68755; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 57883-25-7, 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 57883-25-7, name is 3-Bromo-2-ethoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-bromo-2-ethoxy-pyridine (350 mg, 1 .7 mmol) in NMP (2 ml_) was added Zn(CN)2(244 mg, 2.1 mmol) and Pd(dppf)CI2(127 mg, 0.17 mmol). The mixture was degassed with N2and heated at 140C 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_chi2) and brine (20 ml_), dried over Na2S04, filtered and concentrated. The residue was purified by flash chromatography on silica gel (0%~20% ethyl acetate in petroleum ether) to give 2- ethoxynicotinonitrile.

According to the analysis of related databases, 57883-25-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (270 pag.)WO2018/7249; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1052714-48-3 ,Some common heterocyclic compound, 1052714-48-3, molecular formula is C6H3BrFNO2, 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.

Preparation of 6-Bromo-N-(3,5-dichlorophen l)-3-fluorop ridine-2-carboxamide (Exp- 10-g3)[0126] Into a vessel containing 50 mL of dimethylformamide (DMF) was dissolved lg Exp-10-g2 prepared in the previous step (4.55 mmol) and 0.70g of 3,5- dichlorobenzenamine. Into this solution were added 2.76 g HATU (7.27 mmol) and 1.39g triethylamine (TEA, 13.64 mmol). The reaction mixture thus prepared was stirred at RT overnight, then the mixture was poured into cool water and extracted with EtOAc. The combined organics were washed with brine, dried over MgSC>4, filtered, and concentrated under reduced pressure. The crude product thus obtained was purified on silica column chromatogram (PE/EtOAc = 15: 1-1 : 1) to give 1.28 g of Exp-10-g3 (calculated yield 77.5%). The identity of the product was confirmed by mass spectroscopy in accordance with procedures described herein. MS (ESI): m/z 363, 365, 367, 369 (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,1052714-48-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP; ADDEX PHARMA S.A.; LIVERTON, Nigel; JONES, Philip; BOLEA, Christelle; CELANIRE, Sylvain; TANG, Lam; BOUDOU, Cedric; LEI, Zhiyu; LIU, Fuqing; LUO, Yunfu; DONG, Jingchao; SOLL, Richard; WO2013/60029; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1147422-00-1 ,Some common heterocyclic compound, 1147422-00-1, molecular formula is C12H22N2O2, 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 tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (0.63 g) in acetone (15 mL) was added K2CO3 (1.54 g) and 1-bromo-3-chloropropane (1.45 mL). The reaction mixture was heated to reflux overnight, diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 for 1 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH) to give the title compound as pale yellow liquid (0.65 g, 77.00%).

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. 1147422-00-1, tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Jiancun; Zhang, Yingjun; Zhang, Weihong; Liu, Bing; Zhang, Jiquan; Liu, Jinlei; Zhang, Lu; US2014/228361; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 722550-01-8, 4-(Pyrrolidin-1-yl)pyridin-2-amine, 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, 722550-01-8, blongs to pyridine-derivatives compound. SDS of cas: 722550-01-8

General procedure: 2,4-Dimethoxy-5-[7-(pyrrolidin-1-yl)imidazo|1,2-a]pyridin-2-yl]benzonitrile 63a was prepared in the same manner as 2-(5-bromo-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 9a and was obtained as an off-white solid (62% yield). The resulting compound was treated with HBr to obtain the desired hydrobroniide salt. 1H NMR (400 MHz, DMSO-d6): delta 8.49 (d. J= 7,4 Hz, 1H), 8.23 (s, IH), 8, 14 (s, IH), 7.00 (s, IH), 6.97-6.91 (m, III), 6,31 (s, I H), 4.12 (s, 3H), 4.04 (s, 3H), 3.44 (s, 4H), 2.03 (s, 4H). HPLC (Method 2) 97.12% (AUC), = 18.09 rnm. ESI MS m/z 349 [M + H | +. A solution of 2-bromo-1-(5-bromo-2,4-dimethoxyphenyl)ethanone 7 (124 rng, 0.367 mmol) and 4-(pyrrolidin-1-yl)pyridin-2-amine 8 (60 mg, 0.367 mmol) in acetone (4 mL) was heated at 75 C for 16 h. The reaction mixture was cooled to room temperature; the white precipitate was collected by filtration and solid was washed with acetone. The solid was suspended in aqueous ammonia solution (10 ml.) and stirred for 2 h. The free base was collected by filtration and solid was washed with water, dried under reduced pressure to yield 2-(5-bromo-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 9a (51 mg, 35%) as an off-white solid. 1H NMR (300 MHz, CDCl3): delta 8.55 (s, 1H), 7.83 (d, J = 7.4 Hz, 1H), 7,80 (s, 1H), 6.55 (s, 1H), 6,43 (d, J = 2.2 Hz, 1H), 6.33 (dd, J = 2,2, 7,4 Hz, 1H), 3 ,99 (s, 3H), 3 ,94 (s, 3H), 3.40-3,30 (m, 4H), 2.10-2.00 (m, 4H); HPLC (Method 2) >99% (AUC), tR= 19.12 min: APCI MS m/z 404 [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,722550-01-8, its application will become more common.

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

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. 100848-70-2, name is 2-Methoxy-4-methylpyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H9NO

(a); 9.2 g (69 mmol) of N-chlorosuccinimide was charged to a N,N-dimethylformamide (DMF) 15 ml solution of 8.0 g (65 mmol) of 2-methoxy-4-methylpyridine, followed by stirring for 18 hours. Water was added to the reaction solution, and the aqueous layer was extracted with diethyl ether. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 8.5 g (yield: 82%) of 5-chloro-2-methoxy-4-methylpyridine (melting point 32 to 33C). 1HNMR(CDCl3, 300 MHz): delta 2.32(s, 3H), 3.89(s, 3H), 6.62(s, 1H), 8.05(s, 1H)

The synthetic route of 100848-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1679003; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 212268-12-7, 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 212268-12-7, name is 2-Amino-3-nitro-5-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

(Reference Example 2-2) 5-Fluoro-3-nitropyridine-2-amine (2.66 g) suspended in concentrated hydrochloric acid (35 ml) was cooled to -15C, and an aqueous solution (7 ml) of sodium nitrite (2.57 g) was added dropwise over 10 minutes. After stirring at -10C for 1 hour, and further stirring at room temperature for 1 hour, under ice cooling a 30% aqueous sodium hydroxide solution was added for neutralization. The insolubles were collected by filtration, washed with water, air-dried, and then redissolved in ethyl acetate, before the insolubles were filtered off. The filtrate was concentrated under reduced pressure to afford 2-chloro-5-fluoro-3-nitropyridine (1.41 g). 1H NMR (400 MHz, CDCl3) delta: 8.03 (dd, 1H, J = 6.6, 2.7 Hz), 8.55 (d, 1H, J = 2.7 Hz).

According to the analysis of related databases, 212268-12-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2471792; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 29681-45-6 ,Some common heterocyclic compound, 29681-45-6, molecular formula is C8H9NO2, 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 methyl 5-methylnicotinate (5 g, 33 mmol) in carbon tetrachloride (200 mL) was added NBS (5.9 g, 1 equiv) and dibenzoyl peroxide (1.2 g, 0.15 equiv). The reaction was refluxed for 3 h, then was cooled to RT to give compound 14A. The carbon tetrachloride solution containing compound 14A was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29681-45-6, its application will become more common.

Reference:
Patent; Li, James J,; Hamann, Lawrence G.; Ruan, Zheming; Cooper, Christopher B.; Wu, Shung C.; Simpkins, Ligaya M.; Wang, Haixia; Nayeem, Akbar; Krystek, Stanley R.; US2006/235028; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem