Tag: M.W:100-200

Synthetic Route of 58539-77-8, 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. 58539-77-8, name is 3-(Chloromethyl)-2-methylpyridine hydrochloride. A new synthetic method of this compound is introduced below.

A mixture of the compound of Example 42 (0.20 g, 0.57 [MMOL),] cesium carbonate (2.0 g, 5.7 [MMOL)] and 3-chloromethyl-2-methyl-pyridine hydrochloride (0.16 g, 0.91 [MMOL)] in a 2: 1 THF/DMF mixture was heated at [80C] for 15 hours. The cooled mixture was filtered and concentrated, and then water (30 mL) was added and the mixture extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed with brine, dried [(MGS04),] filtered and concentrated to a foam (0.31 [G).] The residue was purified by flash chromatography using a 30% to 70% ethyl acetate/hexanes eluant to afford 122 mg (47%) of the title compound as an oil. Mass spectrum: (m/e) 458 (M++1, +ion).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58539-77-8, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/5229; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 717843-48-6, 3-Bromo-6-methylpicolinonitrile, 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, HPLC of Formula: C7H5BrN2, blongs to pyridine-derivatives compound. HPLC of Formula: C7H5BrN2

(3) the 2 – bromo -6 – methyl -2 – cyano pyridine (25g, 127mmol) dissolved in the 1L in concentrated hydrochloric acid (HCl), mixture in 110 C stirring reaction under the condition of 2 days; removing the solvent to obtain crude product; the obtained crude product is dissolved in water, and addingNaHCO3, then filtered; the filtrate is ethyl acetate extraction, Na2SO4drying and vacuum concentrated to get the crude product 3 – bromo -6 – methyl -2 – picolinic acid; two product adds up the yield of 69.3%, about 19g.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,717843-48-6, 3-Bromo-6-methylpicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Suzhou Jianxiong Vocational and Technical College; Gu, Zhun; Wang, Yang; Jin, Chen; (7 pag.)CN106045902; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 52313-50-5, Adding some certain compound to certain chemical reactions, such as: 52313-50-5, name is Picolinimidamide,molecular formula is C6H7N3, 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 52313-50-5.

A solution of 1-(2,4-difluorophenyl)piperidin-4-one (0.24 g, 1.14 mmol) and DMFDMA (0.5 mL) in acetonitrile (5 ml) was heated with stuffing at 90 C for 2 hrs. The mixture was concentrated in vacuo and the residue was dissolved in EtOH (lOmL). To the solution was addedpyridine-2-carboxamidine (91 mg, 0.75 mmol) and potassium carbonate (210 mg, L50 mmol) successively. After being heated at 90 C overnight, the resulting mixture was cooled to rt, diluted with water (20 mL) and extracted with EA (20 mL) for three times. The organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep-HPLC to give 6-(2,4-difluorophenyl)-2-(2-pyridyl)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine (6 mg). ?H NMR (400MHz, DMSO-d6): oe 8.77 (s, 1H), 8.74 (d, 1H),8.36 (d, 1H), 7.97 (dt, 1H), 7.52 (ddd, 1H), 7.34 – 7.16 (m, 2H), 7.14 – 6.97 (m, 1H), 4.33 (s, 2H),3.48 (t, 2H), 3.10 (t, 2H). MS obsd. (ESIj [(M+H)]: 325.

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. 52313-50-5, Picolinimidamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5223-06-3 ,Some common heterocyclic compound, 5223-06-3, molecular formula is C9H13NO, 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 100 g (0.655 mol) [2- (5-ETHYL-PYRIDIN-2-YL)-ETHANOL] in 500 mL acetic acid was added 118 g (1.049 mol) 30% hydrogen peroxide at 25-30 [C.] Reaction mixture was refluxed at 100 [C] [(TLC)] for 14 hr. After completion of the reaction acetic acid was removed under vacuum, and the residual mass was poured in excess water and made alkaline by 10% [NA2C03] solution. Product was extracted with ethyl acetate and after concentrating ethyl acetate [IN VACUO, 89. 58 G (81%)] crystalline product was obtained. The product obtained was characterized by Mass, [13C] NMR, [AND’H] NMR, which are as given below. Mass spectrum (m/z) : 168. 1 (M + [H) +] [3C-NMR] [(CDC13)] [: 6] 170.7, 148.2, 138.7, 135.9, 125. 8,62. 0,34. 2,25. 5, 14.4 ‘H-NMR [(CDC13)] : [S] 7.07-8. 14 (3H, m), 5.7 [(1H,] broad s), 3.9 (2H, t), 3.2 (2H, t), 2.6 (2H, q), 1.2 (3 H, t)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5223-06-3, its application will become more common.

Reference:
Patent; CADILA HEALTHCARE LIMITED; WO2004/7490; (2004); A2;,
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. 189281-48-9, name is 2,4-Dichloro-5-fluoropyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 2,4-Dichloro-5-fluoropyridine

Example 10d6-Chloro-2-(4-chloro-phenyl)-3-fluoro-pyridine A solution of 2.2 g 2,4-chloro-5-fluoropyridine, 2.28 g 4-chlorophenylboronic acid and 0.6 g tetrakistriphenylphosphine palladium in 30 ml tetrahydrofuran was added 30 ml of a 10% a solution of potassium carbonate in water and the mixture was stirred at ambient temperature for 18 h. The reaction mixture was diluted with ethyl acetate and water. The phases were separated and the organic phase was washed water, 10% aqueous citric acid, 10% aqueous sodium bicarbonate and brine, dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel with a gradient of heptane_dichloromethane=9:1 to 1:1 (only startspot was removed) The product fractions were collected and evaporated. The residue was subjected to Kugelrohr distillation at 0.03 mbar and 110 C. to yield 1.72 g of the title compound as colorless oil which solidified into white crystals. MS (EI) (M+H): 241 and 243:

The synthetic route of 189281-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hebeisen, Paul; Roever, Stephan; US2012/157476; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 69627-02-7, 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. 69627-02-7, name is Thieno[3,2-b]pyridin-7(4H)-one, molecular formula is C7H5NOS, 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.

To a solution of thieno[3,2-b]pyridin-7-ol (1,2.55g, 16.87 mmol) in acetic acid(50mL) was added bromine(1.7 mL, 32.72 mmol). The mixture was heated at 110C for Ih,cooled and the resultant precipitate was separated by filtration, to afford the title compound270 (4.47g, crude) as a dark brown powder, which was used in next step without furtherpurification. M/S (m/z): 231.9(M+H) (found).

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 69627-02-7, Thieno[3,2-b]pyridin-7(4H)-one.

Reference:
Patent; METHYLGENE, INC.; WO2006/10264; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65977-55-1, 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 65977-55-1, name is 5-Chlorothieno[3,2-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

(A) A mixture of 1019 5-chlorothieno[3,2-b]pyridine (1.8 g, 10.6 mmol), PdCl2(dppf).CH2Cl2 (866 mg, 1.06 mmol) and 57 Et3N (3 mL) in 21 MeOH (15 mL) was stirred overnight at 110 C. under an atmosphere of CO (g) (60 atm). After cooling to rt, the reaction was quenched by the addition of satd. aq NH4Cl (50 mL) and the resulting solution was extracted with EtOAc (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The resultant residue was purified by silica gel chromatography (0-25% EtOAc/petroleum ether) to afford 1020 methyl thieno[3,2-b]pyridine-5-carboxylate (1.7 g, 82%), as a yellow solid. LC/MS: mass calcd. for C9H7NO2S: 193.02, found: 193.8 [M+H]+.

According to the analysis of related databases, 65977-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Meegalla, Sanath; Player, Mark R.; Huang, Hui; Winters, Michael P.; (98 pag.)US2017/291908; (2017); 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.42753-71-9, name is 2-Amino-5-bromo-6-methylpyridine, molecular formula is C6H7BrN2, molecular weight is 187.0372, as common compound, the synthetic route is as follows.SDS of cas: 42753-71-9

To a 2L 3-neck RBF was added CH2Cl2 (900 mL) followed by 2-amino-6-methyl- 5-bromopyridine (74.23 g, 0.39 mol), pyridine-HCl (139 g, 1.2 mol), NaNO2 (83.26 g, 1.2 mol) and CuCl (3.76 g, 5% w/w to starting material). The mixture was cooled to 0-10 0C in an ice- water bath and cone. HCl (4.5 mL, 6% v/w to starting material) was added dropwise and the mixture stirred at 0-10 0C for 30 min. The cooling bath was removed and the mixture was stirred at rt for Ih. The reaction mixture was quenched with saturated aqueous NaHCO3 (400 mL), the layers separated and the aqueous layer was extracted with CH2Cl2 (100 mL). The combined organic layers were concentrated to dryness and hexanes (750 mL) was added to the residue under stirring. The solid was filtered and washed with hexane and the filtrate was concentrated to dryness to afford pure product as a light yellow crystalline solid (61 g, 70%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,42753-71-9, 2-Amino-5-bromo-6-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; ANORMED INC.; WO2007/22371; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 800401-68-7, 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. 800401-68-7, name is 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid, molecular formula is C8H5ClN2O2, 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: To a stirred solution of 10a-d (2.3 mmol) in anhydrous THF (20 mL) dimethylaminopyridine(DMAP, 2.3 mmol) was added, followed by EDCI (1.2 mmol) after 10 min; the reaction mixture wasstirred at room temperature for 1h. The suitable acid 10a-d (1.0 mmol) and EDCI (1.2 mmol) wereadded and the reaction mixture was stirred for 48 h. The solid was collected by filtration, purified byflash chromatography using CH2Cl2/MeOH 98:2 and recrystallized from CH2Cl2 and MeOH, affordingthe desired product as a yellow solid. Compounds 5a-e were characterized only by 1H-NMR spectroscopy.The poor solubility of the title compounds prevented 13C-NMR spectra from being recorded.

According to the analysis of related databases, 800401-68-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Parrino, Barbara; Span, Virginia; Carbone, Anna; Barraja, Paola; Diana, Patrizia; Cirrincione, Girolamo; Montalbano, Alessandra; Molecules; vol. 19; 9; (2014); p. 13342 – 13357;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17282-04-1, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 17282-04-1 as follows.

To a degassed solution of [5-FLUORO-2- (4,] 4,5, 5-tetramethyl- [1, 3,2] dioxaborolan-2-yl) benzonitrile (5.55 g, 22.46 [MMOL),] 2-chloro-3- [FLUOROPYRIDINE] (2.95 g, 22.46 mmol), potassium fluoride (4.3 g, 74.14 mmol) and tris (dibenzylideneacetone) [DIPALLADIUM (0)] (0.824 g, 0. 89 mmol) in THF (80 ml) and water [(8] ml) was added tri (tert-butyl) phosphine (0.51M solution in hexane; 3.52 ml, 1.79 mmol). The reaction was heated at [70C] for 48 h, then allowed to cool to ambient temperature. The reaction mixture was filtered through a catalyst filter, and the filtrate diluted with ethyl acetate (400 ml) and washed with water (2 x 100 ml). The organic phase was separated, dried (MgSO4), filtered and adsorbed onto silica gel. The crude product was chromatographed on silica, eluting with 10% ethyl acetate in isohexane, to give [5-FLUORO-2- (3-FLUOROPYRIDIN-2-YL)] benzonitrile as a white solid (3.02 [G)] : [8H] (400 MHz, [CD13)] 7. [40-7.] 45 (2H, m), 7.51-7. 61 (2H, m), 7.72-7. 76 [(1H,] m), 8.58-8. 60 [(1H,] m); m/z (ES+) 217. To a solution of [5-FLUORO-2- (3-FLUOROPYRIDIN-2-YL)] benzonitrile (1 g, 4.62 mmol) in dichloromethane (10 ml) at [0C] was added urea hydrogen peroxide addition compound (0.91 g, 9.71 mmol) followed by trifluoroacetic anhydride (1.94 g, 1.30 ml, 9.25 mmol) and the mixture warmed to ambient temperature and stirred for 18 h. The reaction was quenched with [NA2S203] (saturated solution; 2 ml) and poured onto 0.5N HCl (20 ml). The aqueous phase was extracted with dichloromethane (2 x 100 ml) and the combined organics dried over [MGS04,] filtered and evaporated to give a red oil. The crude product was chromatographed on silica (0 to 5% methanol in dichloromethane) to give [5-FLUORO-2- (3-FLUORO-1-OXYPYRIDIN-2-] yl) benzonitrile as an amber oil which crystallised on standing (0.687 [G)] : [SN] (400 MHz, CDCl3) 7.24-7. 27 [(1H,] m), 7.36-7. 39 [(1H,] m), 7.45-7. 49 [(1H,] m), 7.56 [(1H,] dd, [J 2.] 7,7. 8), 7.65 [(1H,] dd, [J 5.] 3, 8. 7), 8.29 [(1H,] d, [J 6.] 6); [M/Z] (ES+) 233. To a solution of [5-FLUORO-2-(3-FLUORO-1-OXYPYRIDIN-2-YL)] benzonitrile (0.67 g, 2.88 mmol) in chloroform (3 ml) was added phosphorus oxychloride (11.06 g, 72. 18 mmol) and the mixture heated at reflux for 2 h. After cooling to ambient temperature, the reaction was poured onto ice (150 g) and stirred for 15 mins. Solid sodium carbonate was then added portionwise until pH = 10. The mixture was then extracted with dichloromethane (2 x 150 ml) and the combined organics dried [(MGSO4),] filtered and evaporated to give a cream-coloured solid. The crude product was chromatographed on silica, eluting with 50-25% isohexane in dichloromethane, to give two products. Less polar product 2- (6-chloro-3- [FLUOROPYRIDIN-2-YL)-5-FLUOROBENZONITRILE] (258 mg): aH (400 MHz, CDCl3) 7.41-7. 45 (2H, m), 7.53 [(1H,] dd, [J 2.] 6,7. 9), 7.57 [(1H,] t, [J 8.] 6), 7.74 [(1H,] dd, J 5.4, 8.8) ; m/z (ES+) 251. More polar product [2- (4-CHLORO-3-FLUOROPYRIDIN-] 2-yl)-5-fluorobenzonitrile (115 mg): [8H] (400 MHz, [CD13)] 7.41-7. 45 [(1H,] m), 7.49 [(1H,] t, [J 5.] 1), 7. 55 [(1H,] dd, [J 2.] 6,7. 9), 7.73 [(1H,] dd, [J 1.] 3,14. 1), 8. 47 [(1H,] d, [J 5.] 1); m/z (ES+) [251.] To [2- (8-FLUOROIMIDAZO [1,] 2-a] pyridin-7-yl) propan-2-ol (0.21 g, 1.10 mmol), [2- (6-CHLORO-3-FLUOROPYRIDIN-2-YL)-5-FLUOROBENZONITRILE] (0.25 g, 1.00 mmol) and palladium acetate (0.011 g, 0.05 mmol) in [N, N-] dimethylacetamide (2 ml) was added triphenylphosphine (0.013 g, 0.05 mmol) followed by potassium acetate (0.14 g, 1.51 mmol) and the mixture heated at [130C] for 2 h. The reaction was cooled to ambient temperature, diluted with methanol (8 ml) and 2 drops of acetic acid were added. The mixture was poured onto a strong cation exchange cartridge and eluted with several column lengths of methanol. Several column lengths of 2N ammonia in methanol were then eluted to recover the product. The pale yellow oil was chromatographed on silica, eluting with 3% methanol in dichloromethane, to give the title material as a white powdery solid. Recrystallised from ethyl [ACETATE/ETHER] to afford the title compound (215 mg): aH (400 MHz, CDCl3) 1.73 (6H, s), 2.07 [(1H,] s), 7.26 [(1H,] d, J 14.4), 7.45-7. 49 [(1H,] m), 7.61 [(1H,] dd, [J2.] 6,7. 9), 7.67 [(1H,] t, [J 9.] 0), 7.77-7. 80 [(1H,] m), 7. 88 [(1H,] dd, [J 3.] 3,8. 9), 8. 15 [(1H,] s), 9.59 [(1H,] d, [J 7.] 3); m/z [(ES+)] 409.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17282-04-1, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2003/99817; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem