Day: July 8, 2021

Synthetic Route of 866319-00-8 ,Some common heterocyclic compound, 866319-00-8, molecular formula is C7H5FN2, 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.

i) 5-Fluoro-1H-pyrrolo[2,3-b]pyridine 7-oxide may be prepared in the following manner: 6.22 g of 3-chloroperbenzoic acid are added to a solution of 2.7 g of 5-fluoro-1H-pyrrolo[2,3-b]pyridine in 70 cm3 of dimethoxyethane. The reaction medium is stirred in the region of 20 C. for 1 hour 30 minutes. After addition of a solution of 2 g of potassium hydroxide in 20 cm3 of methanol, the mixture is extracted with 5 times 100 cm3 of ethyl acetate. The organic phases are then washed with twice 15 cm3 of saturated ammonium chloride solution and then dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa) The residue is purified by flash chromatography on a column of silica [eluent: dichloromethane/methanol (95/5 by volume)], and 3.6 g of a solid are obtained, which is washed with 25 cm3 of diethyl oxide and then dewatered and dried. The residue is purified by flash chromatography on a column of silica [eluent: cyclohexane/ethyl acetate (50/50 by volume)], and 1.70 g of 5-fluoro-1H-pyrrolo[2,3-b]pyridine 7-oxide are obtained in the form of a powder, the characteristics of which are as follows: Melting point: melting at 178 C. (Koefler block) IR spectrum: KBr 3128; 3085; 2919; 2863; 2734; 2629; 2406; 1588; 1507; 1349; 1256; 1206; 1129; 1077; 990; 804; 723; 670 and 466 cm-1

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. 866319-00-8, 5-Fluoro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Aventis Pharma S.A.; US2007/93480; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 932-35-4, 3-Hydroxypicolinonitrile, 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, Recommanded Product: 932-35-4, blongs to pyridine-derivatives compound. Recommanded Product: 932-35-4

[00181] To a solution of isopropyl 4-(4-chloro-leta-pyrazolo[3,4-d]pyrimidin-l- yl)piperidine- 1 -carboxylate from Example 19C (63 mg, 0.195 mmol) in 2 mL of DMF was added 3-hydroxypicolinonitrile (23.37 mg, 0.195 mmol) and potassium carbonate (53.8 mg, 0.389 mmol). The reaction was allowed to stir at room temperature for 18 h. The reaction was diluted with ethyl acetate, washed with sat’d aq sodium bicarbonate and brine, dried over MgSO4, filtered through a pad of silica gel and concentrated in vacuo to an oil. The residue was purified by silica gel chromatography (12 g ISCO cartridge, 0-90% ethyl acetate/hexane, 15 min gradient) to afford Example 19 (24 mg, 29%) as an off-white solid. 1H NMR (500 MHz, CDCl3) delta ppm 1.29 (d, J=6.05 Hz, 6 H) 2.02 – 2.08 (m, 2 H) 2.25 – 2.35 (m, 2 H) 2.98 – 3.08 (m, 2 H) 4.38 (s, 2 H) 4.94 – 5.05 (m, 2 H) 7.68 (dd, J=8.52, 4.67 Hz, 1 H) 7.88 (d, J=8.80 Hz, 1 H) 8.27 (s, 1 H) 8.49 (s, 1 H) 8.69 (d, J=4.40 Hz, 1 H). LRMS (ESI): 408.3 (M+H)+.

The synthetic route of 932-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/137436; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 99163-12-9, 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 99163-12-9, name is 4-Pyridin-4-yl-benzaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

25 g (110 mmol) of N-(4-chlorophenyl)-1 ,2-phenylene diamine and 20 g (110 mmol) of biphenyl-4-carboxaldehydewere agitated with 300 mE of 2-methoxy ethanol in a 2000 mE round flask, the temperature of the reaction vessel was increased up to a reflux temperature, and the resultant was agitated for 24 hours. The reaction solution was treated with methylene chloride and water to obtain an organic layer, andanhydrous magnesium sulfate was used to remove moisturefrom the organic layet 12 g of a compound (D) (28% yield)was obtained by colunmizing the resultant after removing asolvent therefrom.Atomic analysis of the compound (D) was performed, andthe results are provided as follows.calcd. C24H16C1N3: C, 75.49; H, 4.22; N, 11. found: C, 75.79; H, 4.11; N, 11.8.

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 99163-12-9, 4-Pyridin-4-yl-benzaldehyde.

Reference:
Patent; CHEIL INDUSTRIES, INC.; Park, Moo-Jin; Yu, Eun-Sun; Chae, Mi-Young; (64 pag.)US9444054; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 5398-44-7, 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.5398-44-7, name is 2,6-Dichloroisonicotinic acid, molecular formula is C6H3Cl2NO2, molecular weight is 192, as common compound, the synthetic route is as follows.

a) A suspension of 2,6-dichloroisonicotinic acid (5.23 g, 27.24 mmol) in toluene (100 ml.) is heated to 800C and then slowly treated with N,N-dimethylformamide di-tert. butylacetal (19.94 g, 98.0 mmol). The mixture becomes slightly yellow and clear. Heating and stirring is continued for 3 h before the solution is cooled to rt, diluted with ether and washed with sat. aq. Na2CO3-solution. The org. extract is dried over MgSO4, filtered and the solvent is evaporated to give 2,6-isonicotinic acid tert.-butyl ester (6.97 g) which solidifies as beige fine needles. 1 H NMR (CDCI3): delta 1.60 (s, 6 H), 7.73 (s, 1 H).

Statistics shows that 5398-44-7 is playing an increasingly important role. we look forward to future research findings about 2,6-Dichloroisonicotinic acid.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2008/29371; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1083169-00-9, 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 1083169-00-9, name is 4-Bromo-2-methoxy-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of intermediate 6c (0.1M solution in THF, 66 mL,6.6 mmol) was added to a solution of 4-bromo-2-methoxy-6-methylpyridine (CAS: 1083169-00-9; 1.21 g, 6.00 mmol) and Pd(/-Bu3P)2 (140 mg, 0.27 mmol). The reaction mixture was stirred at room temperature for 16 h. The mixture was treated with NH4Cl (sat., aq.) and extracted with EtOAc. The organic layer was dried (Na2S04), filtered and the solvent was evaporated in vacuo. The crude mixture was purified by flash column chromatography (S1O2, (0434) EtOAc in heptane, gradient from 100:0 to 80:20) to afford intermediate 31 (1 g, 54%).

According to the analysis of related databases, 1083169-00-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; DE LUCAS OLIVARES, Ana Isabel; TRESADERN, Gary John; CONDE-CEIDE, Susana; (212 pag.)WO2019/243528; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884495-22-1, 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.884495-22-1, name is 5-Bromo-2-fluoropyridin-3-amine, molecular formula is C5H4BrFN2, molecular weight is 191.0011, as common compound, the synthetic route is as follows.

General procedure: To a solution of 76 (120 mg, 0.37 mmol) in dry pyridine (12 mL) under N2 at RT, was added 2,4-difluorobenzenesulphonyl chloride (159 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) dropwise over 5 min. The mixture was stirred at 45 C under N2 for 16 , and the solvent then removed under reduced pressure. The reaction was quenched with a little water and the resulting solid collected by filtration and washed with water and Et2O. Purification was carried out by trituration with hot CH2Cl2/MeOH solution to give 4 as a pale brown solid (65%).

The chemical industry reduces the impact on the environment during synthesis 884495-22-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 139 – 155;,
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.13143-47-0, name is 1-(4-Aminophenyl)-1H-pyridin-2-one, molecular formula is C11H10N2O, molecular weight is 186.21, as common compound, the synthetic route is as follows.Quality Control of 1-(4-Aminophenyl)-1H-pyridin-2-one

Step 2: To a solution of compound 12.2 (7.44 g, 40 mmol) in 100 mL DMF was added NBS(14.2 g, 80 mmol) in small portions. The mixture was stirred at RT overnight. It was diluted with 1000 mL ethyl acetate, washed with brine three times, dried, concentrated and subjected to flash column chromatography using 5 % methanol in DCM to isolate compound 12.3 (7.20 g, 68 %). MS found for C11H9BrN2O (M+H)+ 265.0, 267.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13143-47-0, 1-(4-Aminophenyl)-1H-pyridin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; SCARBOROUGH, Carroll; WO2008/86226; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59782-85-3, 2,5-Dichloronicotinic acid, 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: C6H3Cl2NO2, blongs to pyridine-derivatives compound. Formula: C6H3Cl2NO2

Description 97: methyl 4-(1-(2,5-dichloronicotinamido)cyclopropyl)benzoate (D97)To a solution of 2,5-dichloronicotinic acid (1 .84g, 7.06 mmol) in dry dimethylformamide (15ml) 1 -Hydroxybenzotriazole hydrate (1 .08 g, 7.06 mmol) and 1 -ethyl-3-(3-dimethylaminopropyl) carbodiimide (2.03g, 10.58 mmol), a solution of methyl 4-(1 -aminocyclopropyl)benzoate hydrochloride (D7) (1 .67g, 7.06 mmol) and triethylamine (0.98ml, 7.06 mmol) in dry dimethylformamide (15ml) was added and the resulting mixture was stirred 1 h at room temperature. NH4CI saturated solution (50ml) was added the mixture was extracted with ethylacetate (3x50ml). Collected organics, after solvent evaporation, was purified by Biotage column SNAP-Si (50g) eluting with a mixture dichloromethane/ ethylacetate from 100/0 to 95:5. Collected organics after solvent evaporation afforded the title compound (D97) (1 .03 mg)MS: (ES/+) m/z: 365.1 [MH+] C17H14CI2N203 requires 364.41 H NMR (400MHz ,CHLOROFORM-d) delta = 8.46 (d, J = 2.4 Hz, 1 H), 8.14 (d, J = 2.4 Hz, 1 H), 8.05 – 7.99 (m, 2 H), 7.41 – 7.35 (m, 2 H), 7.17 (s, 1 H), 3.93 (s, 3 H), 1 .50 (s, 4 H).

The synthetic route of 59782-85-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 571189-16-7 ,Some common heterocyclic compound, 571189-16-7, molecular formula is C14H20N4O4, 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 the reaction flask was added compound 39 (5.65 g, 18.34 mmol)Soluble in methanol,0.5 g Pd / C was added,Catalytic hydrogenation at room temperature,TLC tracking, to be completely complete,Diatomaceous earth, the solvent was removed by distillation under reduced pressure,To obtain a crude solid,And then petroleum ether: ether (30: 1) beating to get pink powder,4.75 g of compound 7-10 was obtained by drying,Yield: 93.1%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,571189-16-7, its application will become more common.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Zhang Yinsheng; Gao Yong; Ren Jing; Wang Qinglin; Wang Zhao; (67 pag.)CN106905245; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 960298-00-4, 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. 960298-00-4, name is 2-(Benzyloxy)-4-bromopyridine, molecular formula is C12H10BrNO, 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.

Step 2: mc-tert-butyl O£4i?V4-r2-(benzyloxy)pyridin-4-yl1-3-alphacvclopropyP-(2- methoxyethoxyV 5-(3 -methoxypropyDbenzyl] amino ) carbonylM-hydroxypiperidine- 1 – carboxylate; To a solution of the title compound from step 1 (1.47 eq.) in THF (0.3 M) at -78 0C was added n-BuLi (2.5 M in hexanes, 1.6 eq.). The resulting solution was stirred at -78 0C for 30 min. MgBr2 (0.5 M in Et2O, 1.9 eq.) was added, and the resulting solution was stirred at -78 0C for 30 min. A solution of ketoamide 3.1 (0.1 M in THF, 1 eq.) was added, and the reaction mixture warmed to rt over 16 h, quenched with NaHCO3 (aq., sat.), extracted with 2 x EtOAc. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by automated flash chromatography (SiO2; 10- 80% EtOAc in hexanes) to afford the title compound as a clear, colorless oil.

According to the analysis of related databases, 960298-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2009/70869; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem