Tag: M.W:100-200

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. 1597-33-7, name is 2-Fluoropyridin-3-amine. A new synthetic method of this compound is introduced below., name: 2-Fluoropyridin-3-amine

A solution of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 0.12 g, 0.34 mmol), EDC (0.16 g, 0.84 mmol) and HOBT (0.13 g, 0.84 mmol) in dimethy.formamide (2 ml) was stirred in air at room temperature for 1 h. 2-Fluoropyridin-3-amine (0.04 g, 0.37 mmol) was then added in one charge. The reaction mixture was stirred at 25 C overnight. Another batch of HOBT (0.13 g, 0.84 mmol), EDC (0. 61 g, 0.842 mmol) and 2-fluoropyridin~3-amine (0.04 g, 0.37 mmol) was added into the mixture and heating was continued at 40C for 38 hours. The reaction mixture was diluted with water (30 ml) and extracted with ethyl acetate (60 ml x 3). The organic phases were combined, washed with brine (50 ml x 3), dried over anhydrous MgS04l and concentrated. The residue was purified by chromatography (silica gel, 40 g, eluent: dichloromethane/methanol=50:1 , 1L). The solid was washed by methanol (3 ml x 2) and dried in vacuo to yield the title compound as a grey solid. 31 mg.1HNMR (400 MHz, DMSO-d6): 10.31 (s, 1 H), 8.64-8.61 (m, 3H), 8.26(d, 1 H, J=2.0), 8.04 (dd, 1H, J=2.4, 9.2), 7.97 (d, 1 H, J=4.8), 7.74 (dd, 2H, J=1.6, 4.8), 7.56 (d, 2H, J=7.2), 7.50(d,1 H, J=8.8), 7.43-7.36 (m, 4H), 5.42 (s, 2H).MS (electrospray): m/z [M+H]+ = 400.0

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, 1597-33-7, 2-Fluoropyridin-3-amine.

Reference:
Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 94220-45-8 , The common heterocyclic compound, 94220-45-8, name is 5-Chloro-1H-pyrazolo[4,3-b]pyridine, molecular formula is C6H4ClN3, 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 solution of 5-chloro-1H-pyrazolo[4,3-b]pyridine (500 mg, 3.29 mmol) in 1,4-dioxane (20 mL) and water (5 mL) were added (2-fluorophenyl)boronic acid (500 mg, 3.57 mmol), potassium phosphate (1.4 g, 6.5 mmol) and (2′-aminobiphenyl-2-yl)(chloro)(dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphoranylidene)palladium (100 mg, 0.127 mmol). The reaction was degassed and backfilled with N2 and stirred at 90 C. for 15 hours. After this time it was cooled to r.t., filtered and concentrated to dryness. The residue was purified by silica gel chromatography using 0-100% ethyl acetate in hexanes to afford desired product as yellowish oil (620 mg, 98%). LC-MS calculated for C12H9FN3 (M+H)+: m/z=214.2; found 214.2.

The synthetic route of 94220-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Liu, Kai; Pan, Jun; Sokolsky, Alexander; Vechorkin, Oleg; Ye, Hai Fen; Ye, Qinda; Yao, Wenqing; (75 pag.)US2018/72718; (2018); 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.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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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);,
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 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;,
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

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

Adding a certain compound to certain chemical reactions, such as: 189449-41-0, (4-Chloropyridin-3-yl)methanol, 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, name: (4-Chloropyridin-3-yl)methanol, blongs to pyridine-derivatives compound. name: (4-Chloropyridin-3-yl)methanol

Example 21 3-chloromethyl-4-chloropyridine hydrochloride Thionyl chloride (0.714 mL, 9.78 mmol) was added at room temperature to dry DMF (7 mL). After 30 min the above solution was cannulated into the solution of 3-hydroxymethyl-4-chloropyridine (700 mg, 4.89 mmol) in DMF (3 mL). After 45 min, the product was precipitated by addition of dry ether (100 ml), washed with ether, and dried in vacuum to yield 813 mg (84percent) of the title compound. 1H NMR (CD3 OD) delta 5.00 (s, 2H), 8.31 (d, 1H, J=S), 8.99 (d, 1H, J=5), 9.18 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,189449-41-0, (4-Chloropyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Microcide Pharmaceuticals, Inc.; US5859256; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem