Category: pyridine-derivatives

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.109-04-6, name is 2-Bromopyridine, molecular formula is C5H4BrN, molecular weight is 157.996, as common compound, the synthetic route is as follows.Product Details of 109-04-6

General procedure: The general procedure for the preparation of N-(3-phenyl)-2,2-dichloroacetamide heterocyclic derivatives was as follows. A mixture of 1 mmol aryl(heterocyclic) bromide, 1.5 mmol 3-aminophenylboronic acid, 2 mmol K2CO3, Triphenyl phosphine at 0.4 mmol and palladium acetate at 0.1 mmol were stirred in 6 mL toluene and 6 mL ethanol at 60? under an argon atmosphere. The progress of the reaction was monitored by TLC (petroleum ether/ethyl acetate). After the reaction finished, the reaction mixture was filtered. The filtrate was concentrated to dryness and subjected to flash column chromatography (silica gel), eluting with petroleum ether/ethyl acetate, to give 3-aryl (hetero) aniline.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,109-04-6, 2-Bromopyridine, and friends who are interested can also refer to it.

Reference:
Article; Li, Tianwen; Yang, Yongchong; Cheng, Changmei; Tiwari, Amit K.; Sodani, Kamlesh; Zhao, Yufen; Abraham, Ioana; Chen, Zhe-Sheng; Bioorganic and Medicinal Chemistry Letters; vol. 22; 23; (2012); p. 7268 – 7271;,
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Synthetic Route of 6959-47-3 , The common heterocyclic compound, 6959-47-3, name is 2-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, 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.

The ligand L3 was prepared by modifying an established method bySong et al. [24]. To a 100 mL round bottom flask, 15 mL of doubledistilled water was added, followed by an addition of 2-chloromethylpyridineHCl (4.96 g, 0.03 mol). Cyclohexylamine (1.73 mL,0.015 mol) was added dropwise to the mixture which was stirred for5 min before adding NaOH pellets (2.4 g, 0.06 mol). The mixture wasfurther stirred for 5 days at room temperature and the product was thenextracted with 3×30 mL portions of CHCl3. The organic layers werecombined and dried over MgSO4, yielding a crude product that waspassed through a silica column and eluted with CHCl3. The off-white crystalline solid obtained was isolated in moderate yield (1.8 g, 43%based on cyclohexylamine). 1H NMR (DMSO): delta 1.1 (m, 2H, CH2-cy),1.3 (q, 2H, J=11.1 Hz, CH2-cy), 1.5 (m, 2H, CH2-cy), 1.7 (m, 2H, CH2-cy), 1.8 (d, 2H, J=12.6 Hz, CH2-cy), 2.4 (m, 1H, CH2-cy), 3.8 (s, 4H,N-CH2-py), 7.2 (ddd, 2H, J=7.6, 3.9, 1.1 Hz, CH-py), 7.5 (d, 2H,J=7.6 Hz, CH-py), 7.7 (ddd, 2H, J=8.6, 7.8, 1.7 Hz, CH-py), 8.4 (d, 2H, J=4.9 Hz, CH-py). 13C NMR (DMSO): delta 24.4 (CH2-cy), 25.6 (CH2-cy), 25.7 (CH2-cy), 28.4 (CH2-cy), 32.9 (CH2-cy), 56.0 (N-CH2-py), 59.3(CH-cy), 121.8 (CH-py), 122.0 (CH-py), 136.3 (CH-py), 148.5 (CH-py),160.8 (C-py). IR numax (cm-1): 2923 (w), 2851 (w), 1587 (w), 1440 (w),1359 (s), 1127 (w), 754 (s), 620 (s). Melting point: 57.3-60.1 C. m/z[M+H]+ (calcd): 282.20 (282.40).

The synthetic route of 6959-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chanerika, Revana; Friedrich, Holger B.; Shozi, Mzamo L.; Inorganica Chimica Acta; vol. 495; (2019);,
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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 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Bromo-1H-pyrrolo[2,3-b]pyridine

To a mixture of tert-butyl piperazine- 1-carboxylate (224 mg, 1.2 equiv.), 3-bromo-lH- pyrrolo[2,3-£]pyridine (197 mg, 1 equiv.), RuPhos (9.3 mg, 0.02 equiv.) and Ruphos Pd Gl, MTBE adduct (16.3 mg, 0.02 equiv.) in THF (2 mL), under argon atmosphere, a 1.3 M THF solution of LiHMDS (1.92 mL, 2.5 equiv.) was added. The resulting mixture was purged with argon for 5 min, and was then sealed in a vial and heated at 70 C for 3 h. The reaction mixture was cooled to RT, quenched by an addition of 1 M HC1 (1.5 mL), diluted with EtOAc and poured into a sat. solution of sodium bicarbonate. After extracting with 3 portions of EtO Ac, combined organic extracts were dried, and the solvent was removed in vacuo. The obtained residue was purified by flash chromatography on silica gel (eluting with a cyclohexane/EtOAc gradient, 0-100 % of EtO Ac) to afford the expected product (165 mg). LCMS: MW (calc’d): 302.4; MS (ES+, m/z): 303.2 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 74420-15-8.

Reference:
Patent; E-THERAPEUTICS PLC; JURKOVIC, Mihaela; LANDEK, Ivana Ozimec; POLJAK, Tanja; RO?CIC, Maja; STUBBERFIELD, Colin; VADLAMUDI, Srinivasamurthy; (228 pag.)WO2019/43372; (2019); A1;,
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Pyridine | C5H5N – PubChem

Application of 504-24-5, 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. 504-24-5, name is 4-Aminopyridine. A new synthetic method of this compound is introduced below.

(1) Bromination reaction:In a 100 ml three-necked flask, 3.76 g (0.04 mol)4-aminopyridineAnd 0.04 g of azobisisobutyronitrile were dissolved in 36 ml of carbon tetrachloride,14.95g (0.084mol) of N-bromosuccinimide was added portionwise at 25 C, the reaction was carried out for 20h,After the liquid-phase central control monitored the conversion of 4-aminopyridine and intermediate 3-bromo-4-aminopyridine into the target product 3,5-dibromo-4-aminopyridine,The reaction mixture was cooled to room temperature with stirring, poured into 50ml carbon tetrachloride and stirred, filtered, the filter cake was washed twice with 2 × 30ml carbon tetrachloride, the filtrate was washed once with aqueous sodium bicarbonate solution, saturated salt Water once, spin-dried to remove carbon tetrachloride, and then recrystallized from petroleum ether,9.28 g of a white solid was obtained,Namely 3,5-dibromo-4-aminopyridine,Yield 92.10%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,504-24-5, 4-Aminopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Wohua Chemical Co., Ltd.; Hu Yadong; Yang Benmei; (5 pag.)CN106957259; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 93-60-7, 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 93-60-7, name is Methyl nicotinate. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Lanthanum nitrate hexahydrate (La (NO 3) 3 .6H 2 0, 17.3 mg, 0.04 mmol) and nitrous oxide were added to a Soxhlet reflux vessel containing absorbent cotton and 2.0 g of dried pelletized molecular sieves 5 A (MS 5 A) , Tri-n-octylphosphine (90% purity, 40 muL, 0.08 mmol) and dimethyl carbonate dehydrated by distillation (8 mL) were placed and stirred at room temperature for 1 to 2 minutes. The resulting mixture was heated under heating reflux conditions (bath temperature of 110 C.) for 1 hour. The mixed solution was cooled to room temperature, the solvent component was distilled off under reduced pressure, and the mixture was dried at room temperature under 5 Torr or less for 1 hour to prepare a catalyst. In the reaction vessel, n-hexane (8 mL) as a solvent, 4-nitrobenzoic acid ester (4.0 mmol) as a carboxylic acid ester and benzyl alcohol (4.0 mmol) as a primary alcohol were added in this order. Immediately, the reactor was heated to reflux condition (bath temperature: 90 C.). Refluxing was continued while appropriately checking the progress of the reaction by TLC, and after 5 hours, the completion of the reaction was confirmed by TLC. Thereafter, the reaction mixture was cooled to room temperature, a small amount of water (0.3 to 0.5 mL) was added, and the reaction was stopped by stirring at room temperature for 5 minutes. The reaction mixture was dried over magnesium sulfate, filtered, and the filtrate was concentrated. The product was isolated from the concentrate by silica gel column chromatography (n-hexane: ethyl acetate). The yield was 99%.In Examples 25 to 29 and Comparative Examples 10 to 14, a product was obtained in the same manner as in Example 24, except that the compound shown in Table 4 was used as the carboxylic acid ester and the reaction time was changed. In addition, in Example 30 and Comparative Example 15, production was carried out in the same manner as in Example 24, except that methyl benzoate was used as the carboxylic acid ester, cyclohexanol as the secondary alcohol was used as the alcohol compound, and the reaction time was changed I got things. However, in Examples 26, 27 and 29 and Comparative Examples 11, 12 and 15, as shown in Table 4, the amounts of lanthanum compounds and ligands used were increased. The results are shown in Table 4 including the results of Example 24 and Comparative Example 9.

According to the analysis of related databases, 93-60-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NAGOYA UNIVERSITY; MITSUBISHI RAYON COMPANY LIMITED; SHIHARA, KAZUAKI; HATANO, MANABU; (25 pag.)JP5804472; (2015); B2;,
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 777899-57-7, name is Methyl 2-chloro-5-nitroisonicotinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C7H5ClN2O4

The starting material of tert-butyl ethyl malonate (41.7 g, 222 mmol, 1.2 eq.) was dissolved in anhydrous DMF (100 mL), cooled to 0 C, and stirred for 0.5 h. NaH (14.8 g, 370 mmol, 2 eq.) was added. After stirring for 0.5 h, methyl 2-chloro-5-nitroisonicotinate (40.0 g, 185 mmol, 1.0 eq.) was slowly added and stirred at room temperature for 5 h. The reaction was completely monitored by TLC, quenched with water at 0 C, concentrated, and extracted with EA (3×500 mL). The filtrate was concentrated under reduced pressure and the crude product was purified by silica gel column chromatography (PE: EA = 10: 1) to give the purified product (35g, yield: 51.4%).

With the rapid development of chemical substances, we look forward to future research findings about 777899-57-7.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Li Lin; Yang Xiaoju; (118 pag.)CN109575016; (2019); A;,
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.103999-77-5, name is 2,5-Dichloro-3-fluoropyridine, molecular formula is C5H2Cl2FN, molecular weight is 165.98, as common compound, the synthetic route is as follows.Quality Control of 2,5-Dichloro-3-fluoropyridine

(c) 64.6 g (1.11 mol) of potassium fluoride and 11.25 g (0.074 mol) of caesium fluoride are suspended in 240 ml of sulfolane and the suspension is heated to 140° C. 50 mol of sulfolane are distilled off by decreasing the pressure and then 61.4 g (0.37 mol) of 2,5-dichloro-3-fluoropyridine and 1.45 g (0.0055 mol) of 18-crown-6 in 20 ml of sulfolane are added to the suspension. This reaction mixture is stirred for 35 hours at 140° C. and then taken up in ice water. The product is isolated from the aqueous mixture either by extraction with ether or by steam distillation, affording 48.7 g (88percent of theory) of 5-chloro-2,3-difluoropyridine, b.p. 65°-66° C. at 133 mbar.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,103999-77-5, 2,5-Dichloro-3-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Ciba-Geigy Corporation; US4831148; (1989); A;,
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 53052-06-5, name is Oxazolo[4,5-b]pyridine-2(3H)-thione. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4N2OS

Example 1 Production of 6-(oxazolo[4,5-b]pyridin-2-ylthio)-N-(2,6-diisopropylphenyl)hexanamide Potassium carbonate (64 mg, 0.47 mmol) and 18-crown-6 (11 mg, 0.04 mmol) were added to a solution of 2-mercaptooxazolo[4,5-b]pyridine (64 mg, 0.42 mmol) and 6-bromo-N-(2,6-diisopropylphenyl)hexanamide (150 mg, 0.42 mmol) in DMF (3 ml), and the resulting mixture was stirred at 80 C. for4 hours. After there action solution was diluted with water, the organic layer was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, from which the solvents were distilled off. The residue was purified by silica gel column chromatography (elution solvents: hexane:ethyl acetate=2:1); the resulting crystal was recrystallized from ethyl acetate-hexane, to recover the objective compound of 49 mg (at a yield of 27%) as a colorless needle-like crystal. Melting Point: 94-95 C. IR (KBr) cm-1: 3230, 2965, 1646, 1497, 1403. 1H-NMR (d6-DMSO) delta: 1.14 (12H, d, J=6.8 Hz), 1.52-1.68 (2H, m), 1.68-1.82 (2H, m), 1.82-1.97 (2H, m), 2.33-2.45 (2H, m), 3.11 (2H, sept, J=6.8 Hz), 3.43 (2H, t, J=7.0 Hz), 7.12 (1H, d, J=8.1 Hz), 7.12 (1H, d, J=6.6 Hz), 7.22 (1H, dd, J=8.1, 6.6 Hz), 7.31 (1H, dd, J=8.1, 4.8 Hz), 7.98 (1H, dd, J=8.1, 1.5 Hz), 8.42 (1H, d, J=4.8 Hz), 8.72 (1H, br s). EIMS m/z (relative intensity): 425 (M+), 407 (100). Elementary Analysis: C24H31N3O2S Required: C, 67.73; H, 7.34; N, 9.87; S, 7.53. Found: C, 67.68; H, 7.33; N, 9.86; S, 7.57.

With the rapid development of chemical substances, we look forward to future research findings about 53052-06-5.

Reference:
Patent; Kowa Company, Ltd.; US6362208; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 18437-58-6 , The common heterocyclic compound, 18437-58-6, name is 4-Amino-2-picoline, molecular formula is C6H8N2, 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.

Compound 36: 7-Fluoro-1 -methyl-N-(2-methyl-4-pyridinyl)-4H-imidazor5,1 – ciri ,41benzothiazine-3-carboxamideTo a solution of 4-amino-2-methylpyridine (74.8 mg, 0.692 mmol) in dry 1 ,4-dioxane (1 mL) stirred at room temperature under argon was added trimethylaluminium (2 M in heptanes) (0.346 mL, 0.692 mmol) dropwise and the reaction mixture was stirred for 1 hour. (7-Fluoro-1-methyl-4H-imidazo[5,1-c][1 ,4]benzothiazin-3-yl)carbonyl 2- methylpropyl carbonate (intermediate 67, 36 mg, 0.099 mmol) in dry 1 ,4-dioxane (1 mL) was added dropwise and the mixture was stirred at 80 C for 4 hours. The reaction mixture was cooled to room temperature, quenched with water and extracted with DCM. 1 M NaOH was added in order to separate phases. The organic layers were washed with 0.1 M HCI, then dried using a phase separator filter tube and concentrated under reduced pressure to give a residue which contained the title compound with some impurities. The retained aqueous phase was basified with 1 M NaOH and extracted with DCM. The organic layer was dried using a phase separator filter tube and concentrated under reduced pressure to give a residue containing the title compound together with some impurities. This residue was dissolved in DCM, 1 M HCI was added and mixture stirred vigorously for 1 hour. The layers were separated and the water layer basified with 1 M NaOH. The mixture was was extracted with DCM and the organic layer dried using a phase separator filter tube and concentrated under reduced pressure to give the title compound of >90% purity (by NMR). This 90% pure material was further purified. The residue was dissolved in DCM, water was added and mixture stirred vigorously for 1 hour. The organic layer was dried using a phase separator filter tube and concentrated under reduced pressure to give the title compound after washing with diethyl ether; 1H NMR (500 MHz, CHLOROFORM-d): delta ppm 2.56 (s, 3 H) 2.66 (s, 3 H) 4.41 (s, 2 H) 7.05 – 7.10 (m, 1 H) 7.30 (dd, J=8.16, 2.82 Hz, 1 H) 7.41 (dd, J=5.57, 1.91 Hz, 1 H) 7.50 (dd, J=8.93, 4.81 Hz, 1 H) 7.56 (d, J=1 .68 Hz, 1 H) 8.41 (d, J=5.65 Hz, 1 H) 9.04 (s, 1 H); MS (m/z): 355 [MH]+.

The synthetic route of 18437-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BERTANI, Barbara; CREMONESI, Susanna; GARZYA, Vincenzo; MICHELI, Fabrizio; RUPCIC, Renata; SABBATINI, Fabio Maria; WO2011/151361; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 7169-97-3 ,Some common heterocyclic compound, 7169-97-3, molecular formula is C7H7BrN2O, 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.

N-(5-bromopyridin-2-yl)acetamide (4.30 g, 20 mmol), m-carboxyphenylboronic acid (3.66 g, 22 mmol) was added to a 250 ml pear-shaped bottle.Further, cesium carbonate (13.0 g, 40 mmol) and tetrakistriphenylphosphine palladium (1.2 g, 1 mmol) were successively added.To the above mixture was added 200 ml of acetonitrile/water (V: V = 3: 2). N2 protection,The oil bath was heated to 90 C for 48 h. After the reaction was completed, the reaction solution was cooled to room temperature and suction filtered.The filtrate was adjusted to pH 4 with 6 mol/L hydrochloric acid to precipitate a white solid.After suction filtration, the cake was vacuum dried to give the product 3.53 g, yield 69%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7169-97-3, its application will become more common.

Reference:
Patent; Xi’an Jiaotong University; Zhang Jie; Pan Xiaoyan; Liang Liyuan; Lu Wen; Wang Sicen; He Langchong; Si Ru; Wang Jin; (14 pag.)CN109824582; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem