Tag: M.W:100-200

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. 84249-14-9, name is 2-Amino-4-bromopyridine, molecular formula is C5H5BrN2, 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. COA of Formula: C5H5BrN2

Step 1: N-(4-bromopyridin-2-yl)cyclopropanecarboxamide To a stirring solution of 4-bromopyridin-2-amine (200 g, 1160 mmol) in DCM (2000 mL) and pyridine (183 g, 2310 mmol) was added cyclopropanecarbonyl chloride (157 mL, 1500 mmol) dropwise at 0 C. under a nitrogen atmosphere. The reaction mixture was allowed to stir at 0 C. for 12 h then the reaction mixture was allowed to warm to rt. The reaction mixture was washed with 1N HCl solution (3*500 mL) and brine (500 mL). The organic solution was dried over Na2SO4, filtered and concentrated to give N-(4-bromopyridin-2-yl)cyclopropanecarboxamide (224 g, 80% yield) as a white solid. LCMS (FA): m/z=241.0 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 84249-14-9.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Bharathan, Indu T.; Blackburn, Chris; Ciavarri, Jeffrey P.; Chouitar, Jouhara; Cullis, Courtney A.; D’Amore, Natalie; Fleming, Paul E.; Gigstad, Kenneth M.; Gipson, Krista E.; Girard, Mario; Hu, Yongbo; Lee, Janice; Li, Gang; Rezaei, Mansoureh; Sintchak, Michael D.; Soucy, Francois; Stroud, Stephen G.; Vos, Tricia J.; Wong, Tzu-Tshin; Xu, He; Xu, Tianlin; Ye, Yingchun; US2015/225422; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1678-53-1, 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.1678-53-1, name is 3-Methyl-4-nitropyridine, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.

To a solution of 250 mg (1.86 mmol) of furopyridine 71, 618 mg (4.47 mmol) of nitropicoline 35 in 8 mL of THF was added 4.47 mL (4.47 mmol) of a 1 M solution of TBAF and 732 mg (5.59 mmol) of Huenig’s base. The mixture was stirred at 60 C for 5 days at which point a slurry had formed. The mixture was cooled to room temperature, filtered, and the product washed with 5 mL of THF and dried under vacuum/N2 sweep overnight to give 350 mg (59%) of dimeric furopyridine 72 as a colorless solid: mp 228e229 C; 1 H NMR (500 MHz, CDCl3) d 3.25 (dd, 2H, J 15.8 and 8.1 Hz), 3.72 (dd, 2H, J 15.8 and 9.6 Hz), 5.88 (dd, 2H, J 9.6 and 8.1 Hz), 6.84 (d, 2H, J 5.6 Hz), 7.42 (s, 4H), 8.40 (m, 4H); 13C NMR (125 MHz, CDCl3) d 35.5, 84.8, 105.6, 123.4, 126.1, 141.0, 145.9, 150.2, 166.0. Anal. Calcd. For C20H16N2O2: C, 75.93; H, 5.10; N, 8.86. Found: C, 75.88; H, 5.07; N, 8.89.

The chemical industry reduces the impact on the environment during synthesis 1678-53-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Kuethe, Jeffrey T.; Tetrahedron; vol. 75; 34; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 15069-92-8, Adding some certain compound to certain chemical reactions, such as: 15069-92-8, name is 5-Hydroxypicolinic acid,molecular formula is C6H5NO3, 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 15069-92-8.

5-Hydroxypyridine-2-carboxylic acid (1.50 g) was dissolved in a mixed solvent of tetrahydrofuran (7.5 mL)/N,N-dimethylformamide (7.5 mL), tert-butylamine (1.7 mL), 1-hydroxybenzotriazole (2.20 g), triethylamine (4.5 mL) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.10 g) were successively added, and the mixture was stirred at room temperature for 24 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=33:67?0:100?ethyl acetate_methanol=95:5) to give the title compound (1.05 g) as an orange oil. 1H-NMR (CDCl3) delta: 1.49 (9H, s), 7.23 (1H, dd, J = 2.6 Hz, 8.6 Hz), 7.90-8.01 (2H, m), 8.17 (1H, d, J = 2.6 Hz), 8.57 (1H, br s)

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. 15069-92-8, 5-Hydroxypicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2103620; (2009); 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. 1620-76-4, name is 4-Methylpicolinonitrile, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H6N2

Reference Example 55 4-Methyl-2-pyridinecarbaldehyde diisobutyl aluminium hydride in toluene (1.5 M, 43.5 ml, 65 mmol) was added dropwise to a solution of 2-cyano-4-methylpyridine (7.0 g, 59 mmol) in dichloromethane (180 ml) at -78 C, and the mixture was stirred at the same temperature for 2 hrs.. The reaction mixture was combined with concentrated hydrochloric acid (28 ml) and water (112 ml), and the water layer and the organic layer were separated.. The organic layer was extracted with 2 N hydrochloric acid.. The water layer was combined, neutralized with sodium hydrogen carbonate and extracted with diethyl ether.. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate.. The solvent was evaporated to give the titled compound (2.7 g, 37 %).

The synthetic route of 1620-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1424336; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 137129-98-7, 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. 137129-98-7, name is 6-Chloro-2-methylnicotinic acid, molecular formula is C7H6ClNO2, 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.

HATU (425 mg, 1.12 mmol) was added to a solution of 6-chloro-2-methyl-3-pyridinecarboxylic acid (commercially available, e.g. from Anichem, or may be prepared according to known methods) (160 mg, 0.93 mmol) in DMF (3 ml) and the mixture was treated with DIPEA (0.407 ml, 2.33 mmol). This mixture was stirred for ca. 10 min at ambient temperature. 3-Methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile (may be prepared as described in Description 11) (313 mg, 1.12 mmol) was added as a solution in DMF (2 ml) and stirring was continued for ca. 1 hour. The reaction mixture was partitioned between DCM and sat aq. NaHCO3 solution (20 ml each). The layers were separated and the aqueous was washed with further DCM (2×20 ml). The combined organic layers were dried (hydrophobic frit) and concentrated to leave a dark brown gum. Purification by silica chromatography (Biotage SP4, 25S cartridge), eluting with 12-100% ethyl acetate in isohexane, gave the title compound as a pale cream foam (376 mg).m/z (API-ES) 433/435 [M+H]+ (Cl isotopes)

According to the analysis of related databases, 137129-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beswick, Paul John; Campbell, Alister; Cridland, Andrew; Gleave, Robert James; Heer, Jag Paul; Nicholson, Neville Hubert; Page, Lee William; Vile, Sadie; US2010/22555; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 100-26-5, 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 100-26-5, name is 2,5-Pyridinedicarboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

1) Pyridine-2,5-dicarboxylic acid dibenzyl ester Thionyl chloride (250 mL) and N, N-dimethylformamide (10 mL) were added to a solution of 2, 5-pyridinedicarboxylic acid (60 g) in dichloromethane (360 mL), and the resultant mixture was heated to reflux for 5 hours. After air cooling, the solvent of the reaction solution was evaporated under reduced pressure, and toluene was added to the residue thus obtained. The resultant mixture was further azeotropically evaporated under reduced pressure, and a residue thus obtained was dissolved in dichloromethane (500 mL). A solution of benzyl alcohol (81.7 mL) in dichloromethane (200 mL) was added dropwise to the solution at 0C, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction solution, and the mixture was partitioned. The organic layer was washed with a saturated aqueous solution of sodiumhydrogen carbonate, and then was dried over anhydrous sodium sulfate. After separating the organic layer by filtration, the solvent was evaporated under reduced pressure, to obtain pyridine-2,5-dicarboxylic acid dibenzyl ester (65 g, 52%) as a solid. 1H-NMR (400MHz, CDCl3) delta: 5.42 (2H, s), 5.47 (2H, s), 7.38-7.46 (10H, m), 8.19 (1H, d, J=8.3Hz), 8.44 (1H, dd, J=8.2, 2.1Hz), 9.35-9.36 (1H, m).

According to the analysis of related databases, 100-26-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1803719; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 62150-45-2, 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. 62150-45-2, name is 4-Bromopyridine-2-carbonitrile. A new synthetic method of this compound is introduced below.

PREPARATION 11 N-t-Butoxycarbonyl-3-(2-cyano-4-pyridyl)-(S)-alanine benzyl ester 1,2-Dibromoethane (13 mul, 0.14 mmol) was added, under dry nitrogen, to a stirred suspension of zinc dust (240 mg, 3.6 mmol) in anhydrous tetrahydrofuran (1 ml), then the resulting mixture gently heated until the first sign of boiling was evident and allowed to cool to room temperature; this process was repeated twice, after which trimethylsilyl chloride (15 mul, 0.11 mmol) was added and stirring continued for 15 minutes at room temperature. A solution of benzyl 2(R)-t-butoxycarbonylamino-3-iodopropionate (0.5 g, 1.2 mmol), obtained by the method described in J. Org. Chem., 1992, 57, 3397, in anhydrous tetrahydrofuran (2 ml) was next added over 1 minute. After a further 1.5 hours at room temperature, the reaction mixture was treated with bis(triphenylphosphine)palladium(II) chloride (75 mg, 0.1 mmol), followed by 4-bromo-2-cyanopyridine (Preparation 10; 270 mg, 1.4 mmol), and stirred for 18 hours more at room temperature, before being treated with ethyl acetate (10 ml) and saturated aqueous ammonium chloride solution (5 ml) and then filtered. The organic phase was separated, washed successively with 1M aqueous citric acid solution, saturated aqueous sodium bicarbonate solution and saturated brine, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by chromatography on silica gel, using an elution gradient of ethyl acetate:toluene (0:100 to 25:75), to afford the title compound (250 mg) as an oil which subsequently presented as a white foam, m.p. 74°-76° C. Rf 0.59 (SS 12). [alpha]D25 -24° (c=0.1, CH3 OH). Found: C,66.14; H,5.91; N,10.75. C21 H23 N3 O4 requires C,66.12; H 6.08; N,11.02percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62150-45-2, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5750520; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 626-55-1, 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. 626-55-1, name is 3-Bromopyridine, molecular formula is C5H4BrN, 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.

A mixture of 3.54 g of diisopropylamine and 50 ml of tetrahydrofuran was stirred while cooling in a dry ice-acetone bath. To the reaction mixture, 20 ml of 1.6 M hexane solution of n-butyllithium was added so that the temperature of the reaction mixture did not exceed -40C. The reaction mixture was stirred for 30 minutes. Then, a mixture of 4.74 g of 3-bromopyridine and 5 ml of tetrahydrofuran was added so that the temperature of the reaction mixture did not exceed -60C. The reaction mixture was stirred for further 30 minutes. Crushed dry ice was added to the reaction mixture and then cooling was stopped. The reaction mixture was stirred until the temperature retuned to room temperature. Water was added thereto, most of hexane and tetrahydrofuran was removed under reduced pressure. The residue was washed with tert-butyl methyl ether, and the aqueous layers were collected. To the collected aqueous layers, concentrated hydrochloric acid was added while ice- cooling so that pH of the mixture was made to be 3 and stirred for one hour, followed by extraction with ethyl acetate three times. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 0.69 g of 3-bromo isonicotinic acid.-NMR (DMSO-d6) delta: 8.74 (s, 1H), 8.67 (d, J=4.9 Hz, 1H), 7.69 (d, J=4.9 Hz, 1H)

According to the analysis of related databases, 626-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49221; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 13602-11-4, name is Methyl 6-methylpyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 13602-11-4

Step 3 in N2 condition, compound 3 (10g, 66.2mmol), CCl4(100 ml), NBS is sequentially added in the solution (17.7g, 99 . 3mmol), AIBN (543.5 mg, 3 . 3mmol), reflux reaction 12h, after detecting reaction is complete, concentrated under reduced pressure, by adding water, extraction with ethyl acetate, combined with the phase, ethyl acetate is removed under reduced pressure, the oily compound crocatus obtained. Recrystallization with petroleum ether and ethyl acetate (10:1) finally obtaining the white solid compound 4 (7.8g), yield 51.3%. This step attempts to adopt different post-processing method, of column chromatography, recrystallization effect is not good, and recrystallization to obtain product is a white solid, no other color.

With the rapid development of chemical substances, we look forward to future research findings about 13602-11-4.

Reference:
Patent; Shanghai Institute Of Technology; Yao, Zhiyi; Zhang, Xiaopan; Zong, Haoqiang; Wang, Dongsheng; (14 pag.)CN105294552; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71935-32-5, 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. 71935-32-5, name is 4-(Hydroxymethyl)picolinonitrile. A new synthetic method of this compound is introduced below.

In toluene, 4-hydroxymethylpyridine-2-carbonitrile (111 mg, 0.83 mmol) synthesized in Production Example 87 was dissolved, and thionyl chloride (73 muL) was added thereto. The mixture was refluxed for 30 minutes. Thereafter, the mixture was allowed to cool down to a room temperature and stirred for one hour. After the completion of the reaction was confirmed by HPLC, the solvent was distilled off. The resulting residue was used for the next reaction without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71935-32-5, its application will become more common.

Reference:
Patent; ASKA Pharmaceutical Co., Ltd; Okada, Makoto; Hasumi, Koichi; Nishimoto, Takahiro; Yoshida, Miwa; Ishitani, Kouki; Aotsuka, Tomoji; Kanazawa, Hashime; US2013/85127; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem