Day: June 29, 2021

Application of 1060812-84-1, 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 1060812-84-1, name is 5-Bromopyrazolo[1,5-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5-bromopyrazolo[1,5-alpyridine (0.15 g, 761.30 pmol), 1-[4-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenyllcyclopropanecarbonitrile (245.88 mg, 913.56 jimol), Pd(t-Bu3P)2 (58.36 mg, 114.19 pmol) and K3P04 (323.20 mg, 1.52 mmol) in dioxane (2 mL) and H20 (0.2 mL) was stirred at 80 C for 16 hours. The crude product was cooled to r.t., dilutedwith H20 (10 mL), extracted with EtOAc (30 mL x 2). The combined organic phase was washed with brine (10 mL), dried over Na2504, filtered and concentrated to give the crude product. The crude product was purified by silica gel column (PE: EtOAc = 10:1 to 5:1 to 1:1) to give 1 -(4- pyrazolo[1,5-alpyridin-5-ylphenyl)cyclopropanecarbonitrile (150 mg, 76% yield) as a solid. ?H NMR (400 MHz, CDC13) 011 8.53 (d, 1H), 7.99 (d, 1H), 7.72 (d, 1H), 7.64 (d, 2H), 7.41 (d, 2H),7.00 (dd, 1H), 6.58 (d, 1H), 1.83 – 1.78 (m, 2H), 1.50 – 1.46 (m, 2H).

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 1060812-84-1, 5-Bromopyrazolo[1,5-a]pyridine.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew Mark; MARRON, Brian Edward; (168 pag.)WO2018/98500; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16179-97-8 , The common heterocyclic compound, 16179-97-8, name is 2-(Pyridin-2-yl)acetic acid hydrochloride, molecular formula is C7H8ClNO2, 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.

intermediate 9: step amethyl 5-bromo-2-(2-(pyridin-2-yl)acetamido)benzoateInto a 250-mL round-bottom flask was placed a solution of methyl 2-amino-5-bromobenzoate (5 g, 21.73 mmol), 2-(pyridin-2-yl)acetic acid hydrochloride (4.5 g, 25.92 mmol), HATU (10 g, 26.30 mmol) and D1EA (8.5 g, 65.77 mmol) in /V,N-dimethylformamide (100 mL). The resulting solution was stirred overnight at 20 C. The reaction was then quenched by the addition of 100 mL of water. The resulting solution was extracted with 3×100 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/mefhanol (1 :50) to afford the title compound as a red solid.

The synthetic route of 16179-97-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARBAY, Kent; EDWARDS, James, P.; KREUTTER, Kevin, D.; KUMMER, David, A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald, L.; WOODS, Craig, R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell, D.; LEONARD, Kristi, A.; WO2015/57203; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13228-40-5, 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. 13228-40-5, name is 2-(2-Pyridyl)indole, molecular formula is C13H10N2, 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.

2 – (piperidin – 2 – yl) – 1 H – indoleAt room temperature, the compound 6 c (0.5 g, 2 . 57 mmol) dissolved in acetic acid (10 ml), then two platinum oxide (0.116 g, 0 . 514 mmol) is added to the reaction, vacuum, hydrogen replacement for three times, the hydrogen in the lower, 50 C stirring reaction for 4 hours. The reaction liquid filtering, turns on lathe does, then with saturated sodium bicarbonate solution to regulate pH ? 8, aqueous phase methylene chloride (30 ml × 3) extraction, the combined organic phase with saturated salt water (50 ml) washing, anhydrous sodium sulfate drying, filtering, turns on lathe does to obtain a yellow solid compound 6 d (0.35 g, yield: 68%).

According to the analysis of related databases, 13228-40-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Fan Jiang; Wei Yonggang; Liu Zhenhong; Qin Linlin; (65 pag.)CN106928126; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 53014-84-9, 2-Methyl-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, Application In Synthesis of 2-Methyl-5-formylpyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Methyl-5-formylpyridine

C. Preparation of 6-methylnicotinaldehyde oxime To a solution of 6-methylnicotinaldehyde (1.67 g, 13.79 mmol) in 27.6 mL MeOH, hydroxylamine (50% weight in water, 0.87 mL, 14.2 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and then at 40 C. for an additional 2 h. The reaction mixture was concentrated to obtain 1.76 g (94%) of the title compound as a light brown solid. HPLC: retention time=0.20 min.

The synthetic route of 53014-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun, Chongqing; Sher, Philip M.; Wu, Gang; Ewing, William R.; Huang, Yanting; Lee, Taekyu; Murugesan, Natesan; Sulsky, Richard B.; US2007/4772; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 104830-06-0, 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. 104830-06-0, name is 2-Amino-3-iodopyridine, molecular formula is C5H5IN2, 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.

General procedure: A solution of the substituted 2-iodoaniline or 2-bromoaniline (1.0 equiv), DMAP (0.05 equiv) and NEt3 (2.0 equiv) was prepared in CH2Cl2 (2mL) and cooled to 0 C. The acyl chloride solution was added dropwise into the solution. After 5 minutes, the reaction was allowed to warm to room temperature and was stirred overnight. The reaction was quenched with a saturated NaHCO3 solution and extracted with CH2Cl2 twice. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting crude amide was used in next step without further purification.

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 104830-06-0, 2-Amino-3-iodopyridine.

Reference:
Article; Xiao, Genhua; Chen, Liang; Deng, Guobo; Liu, Jianbing; Liang, Yun; Tetrahedron Letters; vol. 59; 19; (2018); p. 1836 – 1840;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 60290-21-3, Adding some certain compound to certain chemical reactions, such as: 60290-21-3, name is 4-Chloro-1H-pyrrolo[3,2-c]pyridine,molecular formula is C7H5ClN2, 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 60290-21-3.

General procedure: To a solution of 4-chloro-lH-pyrrolo-[3,2-c]-pyridine [60290-21-3] (2.0 g, 13.1 mmol) dissolved in DMF (30.5 mL, 0.944 g/mL, 393.2 mmol) at 0C was added portionwise sodium hydride (1.1 g, 28.8 mmol). The reaction mixture was allowed to reach rt and stirred 45 min, after which it was re-cooled to 0C and l-bromobutane (2.1 mL, 1.27 g/mL, 19.7 mmol) was added dropwise. The mixture was then allowed to reach rt and stirred overnight. NaHC03 sat solution was added and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with water and brine, then dried over MgS04 and concentrated in vacuo. The crude residue was purified by column chromatography (silica gel; gradient Heptane/EtOAc from 100/0 to 50 /50) to yield 1-1 (2.7 g, 98.7%) as a yellow liquid

According to the analysis of related databases, 60290-21-3, 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; TRESADERN, Gary John; MARTINEZ LAMENCA, Carolina; LEENAERTS, Joseph Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (171 pag.)WO2019/243535; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16179-97-8, 2-(Pyridin-2-yl)acetic acid hydrochloride, 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, Quality Control of 2-(Pyridin-2-yl)acetic acid hydrochloride, blongs to pyridine-derivatives compound. Quality Control of 2-(Pyridin-2-yl)acetic acid hydrochloride

To a suspension of 5-nitroindoline (3.28 g), 2- pyridylacetic acid hydrochloride (3.82 g), 1- [3- (dimethylamino) PROPYL]-3-ETHYLCARBODIIMIDE hydrochloride (4.22 g) and 1-hydroxybenzotriazole hydrate (3.37 g) in dichloromethane (100 ml) was added dropwise triethylamine (4.45 g) at ambient temperature and the resultant solution was stirred at ambient temperature for 18 hours. The mixture was poured into water and the separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to give 5-nitro-l- (2-pyridinylacetyl) indoline (3.58 g) as a yellow solid. 1H-NMR (DMSO-d6) : 8 3.26 (2H, t, J=8.5 Hz), 4.10 (2H, s), 4.33 (2H, t, J=8.5 Hz), 7.25-7. 35 (1H, m), 7.38 (1H, d, J=7.8 Hz), 7.75- 7.9 (1H, m), 8.1-8. 2 (3H, m), 8.50-8. 55 (1H, m) APCI-MS (m/z): 284 (M+H) +

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16179-97-8, 2-(Pyridin-2-yl)acetic acid hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; DAISO CO., LTD.; WO2004/39795; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 72990-37-5, 3-Chloroisonicotinaldehyde, 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, 72990-37-5, blongs to pyridine-derivatives compound. Formula: C6H4ClNO

EXAMPLE 38 Production of 3-((3-chloropyridin-4-yl)methyl)-5-(methoxycarbonyl)-2-methylindole (67) According to the method of Example 33, obtained is 3-((3-chloropyridin-4-yl)methyl)-5-(methoxycarbonyl)-2-methylindole (67) (0.355 g) from 5-(methoxycarbonyl)-2-methylindole (0.486 g), 3-chloropyridine-4-carboxyaldehyde (0.40 g), triethylsilane (0.896 g) and trifluoroacetic acid (0.439 g). 1H-NMR (CDCl3, delta ppm): 2.38 (3H, s), 3.89 (3H, s), 4.16 (2H, s), 6.82 (1H, d, J=5.0 Hz), 7.33 (1H, d, J=8.5 Hz), 7.87 (1H, d, J=8.7 Hz), 8.08 (1H, s), 8.20 (1H, brs), 8.25 (1H, d, J=5.0 Hz), 8.57 (1H, s).

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; Cell Pathways, Inc.; US6410584; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58530-50-0, 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.58530-50-0, name is 2-(Pyridin-2-yloxy)acetic acid, molecular formula is C7H7NO3, molecular weight is 153.14, as common compound, the synthetic route is as follows.

General procedure: To the mixture of compounds (IVa-c)(2 mmol) in dry acetonitrile (15 mL), triethylamine(3 mmol) followed by substituted piperazines(2 mmol) was added. The mixture was stirred for30 min and TBTU (2mmol) was then added and stirring was continued at room temperature under an inert atmosphere for 10-24 h; the completion of thereaction was monitored by TLC using chloroform-methanol (9 : 1) as eluent. The solvent was evaporatedat reduced pressure, quenched by the addition of coldwater (20 mL), and the obtained solids (Va), (Vb), (Vc),(Vd), (Ve), (Vf), (Vi), and (Vk) were filtered, dried, andrecrystallized from ethanol. In contrast, compounds(Vg), (Vh), (Vj), and (Vl) were obtained by extractingwith ethyl acetate. The extract was washed successivelywith a solution of 10% HCl (20 mL), 10% NaHCO3(20 mL), and water (20 mL). The organic layer wasdried over anhydrous sodium sulfate and evaporated,the crude product was purified by column chromatography (eluent: hexane-dichloromethane-acetone,5 : 3 : 2) to achieve pure piperazine derivatives. Thephysical and analytical data of the synthesized titlecompounds (Va-l) are given below.

The chemical industry reduces the impact on the environment during synthesis 58530-50-0, I believe this compound will play a more active role in future production and life.

Reference:
Article; Al-Ghorbani; Rekha; Lakshmi Ranganatha; Prashanth; Veerabasappagowda; Khanum; Russian Journal of Bioorganic Chemistry; vol. 41; 5; (2015); p. 554 – 561; Bioorg. Khim.; vol. 41; 5; (2015); p. 554 – 561,8;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 561297-96-9 ,Some common heterocyclic compound, 561297-96-9, molecular formula is C6H7FN2, 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 stirred solution of (R) -2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2-phenylpropanoic acid (1.54 g, 3.96 mmol) , HATU (1.65 g, 4.34 mmol) and DIPEA (1.53 g, 15.15 mmol) in THF (30 ml) was added (5- fluoropyridin-2-yl) methanamine (0.50 g, 3.97 mmol) . The reaction mixture was stirred at r.t. for 15h. After completion, the reaction mixture was washed with H 2O (20 ml) and then extracted with DCM (25 ml X 2) . The organic layer was dried over Na 2SO 4, filtered and then concentrated under reduced pressure to afford a residue. The residue was purified by column chromatography with DCM: MeOH (30: 1) to afford the product (1.37 g, 70%) . 1H NMR (400 MHz, DMSO-d6) delta 8.41 (d, J = 4Hz, 1H) , 8.26 (s, 1H) , 8.23 (t, J = 4Hz, 1H) , 8.05 (s, 2H) , 7.95 (s, 1H) , 7.67 (td, J = 8Hz, 4Hz, 1H) , 7.53 (dd, J = 8Hz, 4Hz, 1H) , 7.34-7.20 (m, 6H) , 6.74 (s, 1H) , 4.41 (qd, J = 16Hz, 4Hz, 2H) , 2.38 (s, 3H) ppm. MS: M/e 498 (M+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. 561297-96-9, 2-(Aminomethyl)-5-fluoropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; ZHOU, Changyou; (152 pag.)WO2019/196803; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem