Tag: M.W:200-300

Application of 90145-48-5, 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. 90145-48-5, name is 5-Bromopyridine-2-carboxamide, molecular formula is C6H5BrN2O, 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-Benzothienylboronic acid (1.8 mmol), 5-bromopyridine-2-carboxamide (1.2 mmol), 2M K2CO3 (2.4 mL), Pd(dppf)Cl2 (0.12 mmol) were mixed and stirred at 80 C. in DMF for 3 h. The reaction mixture was filtered and to the filtrated was added EtOAc and H2O. The layers were separated and the aqueous phase was extracted twice with EtOAc. The organic extracts were dried over Na2SO4. The solvent was evaporated in vacuo to give a brown solid. The crude was subjected to reverse phase HPLC to afford the title compound as a light brown solid (11 mg). 1H NMR delta ppm 9.07 (d, 1H) 8.34 (dd, 1H) 8.24-8.02 (m, 5H) 7.73 (s br, 1H) 7.54-7.37 (m, 2H); MS m/z 255 (M+H).

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 90145-48-5, 5-Bromopyridine-2-carboxamide.

Reference:
Patent; AstraZeneca AB; US2008/221149; (2008); 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.100397-96-4, name is 1-(4-Bromophenyl)-2-(pyridin-4-yl)ethanone, molecular formula is C13H10BrNO, molecular weight is 276.13, as common compound, the synthetic route is as follows.Computed Properties of C13H10BrNO

1-(4-bromophenyl)-2-(pyridin-4-yl)ethanone (4 g, 14.5 mmol) was heated at reflux in DMF-DMA (13 ml) for 1 hour and concentrated. The residue was dissolved in MeOH, and to this, methylhydrazine in water (40%) (3 ml) was added. Then the reaction mixture was heated at 65 C. for 1 hour. When LC/MS indicated the reaction was completed. The mixture was concentrated and purified by column chromatography over silica gel using (PE:EA=10:1-1:1) to give 3 g of crude product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100397-96-4, 1-(4-Bromophenyl)-2-(pyridin-4-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; SU ZHOU JING HONG BIOTECH CO., LTD.; CAI, Zhen-Wei; ZHOU, Ding; LIN, Yougang; CHEN, Ping; US2013/158031; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15862-50-7, 3-Bromo-2-methoxy-5-nitropyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A mixture of 3-bromo-2-methoxy-5-nitropyridine (30b; 5.56 g, 23.86 mmol), potassium trifluoro(vinyl)borate (6.39 g, 47.7 mmol), PdCl2Amphos2(0.338 g, 0.477 mmol), and potassium carbonate (35.8 mL, 71.6 mmol) in dioxane (119 mL) was stirred at 80 C for 30 min. The reaction mixture was then diluted with DCM (200 mL) and washed with saturated aqueous ammonium chloride (2×100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo to give 2-methoxy-5-nitro-3-vinylpyridine (4.90 g, 27.2 mmol, >99% yield) as a yellowish-tan solid.

The synthetic route of 15862-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lanman, Brian A.; Reed, Anthony B.; Cee, Victor J.; Hong, Fang-Tsao; Pettus, Liping H.; Wurz, Ryan P.; Andrews, Kristin L.; Jiang, Jian; McCarter, John D.; Mullady, Erin L.; San Miguel, Tisha; Subramanian, Raju; Wang, Ling; Whittington, Douglas A.; Wu, Tian; Zalameda, Leeanne; Zhang, Nancy; Tasker, Andrew S.; Hughes, Paul E.; Norman, Mark H.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 24; (2014); p. 5630 – 5634;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1159812-31-3 , The common heterocyclic compound, 1159812-31-3, name is 7-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine, molecular formula is C7H6BrN3, 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.

7-bromo-2-methyl-[l,2,4]triazolo[l,5-a]pyridine (50.9 mg, 0.240 mmol), potassium acetate (70.7 mg, 0.720 mmol), 2nd generation XPhos precatalyst (14.16 mg, 0.018 mmol) and bis(pinacolato)diboron (60.9 mg, 0.240 mmol) were added to a 40 mL reaction vial and evacuated and charged multiple times with nitrogen. Added dioxane (1920 mu), then evacuated and charged the vessel again with nitrogen (3x). Heated to 100C and monitored by LCMS for loss of bromopyrazole. Once bromopyrazole was consumed, the reaction was cooled to room temperature and 2-bromo-6-chloro-3-(l-((l-fluorocyclopentyl)methyl)-lH-pyrazol-4-yl)-5-methylpyridine (INTERMEDIATE H6, 89 mg, 0.240 mmol) was added along with l, l’-bis(di-tert- butylphosphino)ferrocene palladium dichloride (9.39 mg, 0.014 mmol). The reaction was evacuated and charged 3x with nitrogen, followed by the addition of 3M aqueous potassium carbonate (240 mu, 0.720 mmol). Heated to 50C overnight. Partitioned between water and ethyl acetate. Extracted the aqueous twice more with ethyl acetate. The organics were passed over a bed of sodium sulfate and the filtrate evaporated. Purified by silica gel chromatography, eluting with 20-100% 3 : 1 EtOAc:EtOH in hexanes to give the title compound. MS(M+1): 425.

The synthetic route of 1159812-31-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; ACTON, John, J., III; BAO, Jianming; DENG, Qiaolin; EGBERTSON, Melissa; FERGUSON, Ronald, III; GAO, Xiaolei; HARRISON, Scott Timothy; KNOWLES, Sandra, L.; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert, D., Jr.; MENG, Zhaoyang; NA, Meng; RUDD, Michael, T.; SELYUTIN, Oleg, B.; TELLERS, David, M.; TONG, Ling; ZHANG, Fengqi; (195 pag.)WO2019/5587; (2019); 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.153034-88-9, name is 2-Chloro-4-iodo-3-methylpyridine, molecular formula is C6H5ClIN, molecular weight is 253.4681, as common compound, the synthetic route is as follows.category: pyridine-derivatives

The mixture of 1.0 g of 2-chloro-4-iodo picoline, 84 mg of palladium acetate, 218 mg of 1,1′-bisdiphenylphosphino ferrocene, 990 mg of sodium hydrogen carbonate, 10 mL of N,N-dimethylformamide, and 10 ml of methanol, was stirred overnight in a carbon monoxide atmosphere at 80C. After cooling the reaction mixture back to room temperature, water and a saturated aqueous solution of sodium hydrogen carbonate were added thereto, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 522 mg of 2-chloro-3-methylisonicotinic acid methyl ester [48-1] as a colorless oily product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-88-9, 2-Chloro-4-iodo-3-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1790650; (2007); 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. 25813-25-6, name is 3,5-Dibromopyridin-4-ol, the common compound, a new synthetic route is introduced below. Application In Synthesis of 3,5-Dibromopyridin-4-ol

Compound (M-41) (10.0 g, 39.5 mmol) was suspended in acetonitrile (50 mL), DIPEA (15 mL, 87 mmol) wasadded at room temperature, phosphoryl chloride (7.4 mL, 79 mmol) was added under ice-cooling, and the mixture wasstirred with heating under reflux for 17 hr. The mixture was allowed to cool, and the reaction mixture was added dropwiseto ice water, and neutralized with sodium carbonate (11.6 g, 138 mmol). Thereafter, the mixture was extracted with ethylacetate, and the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solventwas evaporated under reduced pressure to give a chloro compound (yield 10.6 g, 99%) as a brown solid. The chlorocompound (10.6 g, 39.1 mmol) was dissolved in THF (70 mL), sodium methoxide (28% methanol solution, 14 mL, 59mmol) was added, and the mixture was stirred at 60C for 30 min. The mixture was allowed to cool, water was addedto the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successivelywith water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reducedpressure to give compound (VII-46) (yield 9.21 g, 88%) as a yellow solid

The synthetic route of 25813-25-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; WATANABE, Atsushi; SATO, Yuuki; OGURA, Keiji; TATSUMI, Yoshiyuki; (331 pag.)EP3351533; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 116986-09-5 ,Some common heterocyclic compound, 116986-09-5, molecular formula is C8H8BrNO2, 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.

A mixture of 2-hydroxyl-5-methoxybenzaldehyde (leq) and methyl 3-(bromomethyl)picolinate (leq) was dissolved in anhydrous N,N-Dimethylformamide (DMF). Anhydrous potassium carbonate (K2CO3) (1.2eq) was added to this mixture and the reaction was stirred at room temperature for 8-10 hours. The solvent was then evaporated and the reaction mixture extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and the solvent evaporated. The crude product was purified using S1O2 column chromatography and eluted with the solvent system EtOAc: hexanes = 3:2 to obtain pure product as pale yellow powder with a yield of 82%. IR (Diamond, cm-1): 2897, 1712, 1671, 1607, 1567, 1490, 1445, 1398, 1365, 1275, 1232, 1 165, 1 139, 1 106; 1H-NMR (400 MHz, DMSO-d6): d 10.35 (s, 1H), 8.65 (dd, J = 4.6, 1.28 Hz, 1H), 8.2 (dd, J = 7.84, 0.76 Hz, 1H), 7.66 (dd, J= 7.88, 4.68 Hz, 1H), 7.24 (m, 3H), 5.49 (s, 2H), 3.83 (s, 3H), 3.77(s, 3H); 13C-NMR (100 MHz, DMSO-d6): d 188.81, 166.12, 154.66, 153.55, 148.49, 146.69, 136.89, 133.04, 126.43, 124.89, 122.96, 1 15.79, 1 10.68, 67.44, 55.56, 52.34. MS (ESI) m/z found 324.08 (M+Na)+, Calculated 301.2940 [M]+. The purity of the compound was checked by HPLC and was found to be 98% pure.

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. 116986-09-5, Methyl 3-(bromomethyl)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIRGINIA COMMONWEALTH UNIVERSITY; THE CHILDREN’S HOSPITAL OF PHILADELPHIA; SAFO, Martin, K.; ZHANG, Yan; PARAGE, Piyusha, Pradeep; XU, Guoyan; GHATGE, Mohini; VENITZ, Jurgen; ABDULMALIK, Osheiza; (78 pag.)WO2019/182938; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 623585-74-0, name is Methyl 2,5-dichloroisonicotinate. A new synthetic method of this compound is introduced below., Quality Control of Methyl 2,5-dichloroisonicotinate

To a cold solution of methyl 2,5-dichloroisonicotinate (500 mg, 2.42 mmol) in THF (15 mL) was added N-Methyl-2-pyrrolidone (1.4 mL), iron(III)acetyl acetone (43 mg, 0.12 mmol) and methyl magnesium bromide (36 mg, 0.305 mmol) at 0C. The reaction mixture was stirred at 0C for 1 h and then at rt for 18 h. The reaction mixture was quenched with brine and was extracted with ethyl acetate. The organic layer was separated, dried, filtered and concentrated to afford 130 mg of the title product.1H NMR (300 MHz, DMSO d6): delta 8.46 (s, 1H), 7.74 (s,lH), 3.87 (s, 3H), 2.44 (s, 3H).

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, 623585-74-0, Methyl 2,5-dichloroisonicotinate.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; BANERJEE, Abhisek; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/72825; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73112-16-0, Adding some certain compound to certain chemical reactions, such as: 73112-16-0, name is 2,6-Dibromo-4-methylpyridine,molecular formula is C6H5Br2N, 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 73112-16-0.

(Synthesis of aromatic compound P2)Aromatic compound P2 was synthesized according to the following reaction formula. [Chemical Formula 119]Aromatic compound P2[0139] First, compound 2(l,4-bis-(2-bromo-4-methylpyridm-6-yl)-3,4-diaminobenzene) to be used as the starting material was synthesized via 4,7-bis-(2-bromo-4-methylpyridin-6-yl)-2, 1 ,3-benzothiadiazole.[0140] Specifically, 4.930 g of 2,6-dibromo-4-methylpyridine (0.0196 mol) and 0.762 g of 4,7-bis-pinacolato-diborane-2,l ,3-benzothiadiazole (0.00196 mol) were dissolved in 120 ml of toluene to obtain a toluene solution. To the toluene solution there were added 10 ml of an aqueous solution dissolving 10 g of K2C03, and 0.032 g of trioctylmethylammonium chloride (trade name: Aliquat336 by Aldrich Co., hereunder referred to as “Aliquat336”). After deaerating the solution with argon, 0.1132 g of tetrakis-(triphenylphosphin)-Pd(0)(0.098 mmol) was added and the mixture was heated at 80C for 1 week. This was followed by column purification (dichloromethane/hexane/ethyl acetate) to obtain 0.507 g of 4,7-bis-(2-bromo-4-methylpyridin-6-yl)-2, 1 ,3-benzothiadiazole at a yield of 54% .Results of NMR analysis and MS analysis of 4,7-bis-(2-bromo-4-methylpyridin-6-yl)-2, 1 ,3-benzothiadiazole-NMR (250 MHz, CD2C12): delta = 8.684 ppm (s, 2H); 8.625 ppm (s, 2H); 7.385 ppm (s, 2H); 2.484 ppm (s, 6H)MS(FD, 8 kV) Found: m/z 476.2 (M ), Calculated: m/z: 476.19 (M+)

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. 73112-16-0, 2,6-Dibromo-4-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; Max Planck Gesellschaft zur Foerderung der Wissenschaften e. V.; KOSHINO, Nobuyoshi; HIGASHIMURA, Hideyuki; MUELLEN, Klaus; MALOTKI, Christian von; SU, Qi; BAUMGARTEN, Martin; NOROUZI-ARASI, Hassan; ARNOLD, Lena; LIU, Ruili; WO2011/52805; (2011); 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. 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To a solution of sodium hydride [(1 .52 g, 63.17 mmol (95%)] in DMSO (20.0 mL) at 0 00 diethylmalonate (10.11 g, 63.17 mmol) was added and kept for reflux at 100 00 forlh. The reaction mixture was cooled to room temperature and intermediate 32b(10.0 g, 42.11 mmol) was added drop wise in DMSO (20 mL) to the resulting solutionand refluxed at 10000 for 3 h. The reaction mixture was quenched with ice water and extracted by using Ethyl acetate washed with water, and dried over anhydrous Na2SO4 The solvent was removed under vacuo to yield the title compound (10.0 g, 75.00%) as a brown oily product. LOMS: (M-H) = 315.0

The synthetic route of 75806-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202580; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem