Tag: M.W:100-200

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. 101990-70-9, name is 5-(Chloromethyl)-2-methoxypyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H8ClNO

A mixture of N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (Intermediate 13), (120 mg), 5-(chloromethyl)-2-methoxypyridine (69 mg) and cesium carbonate (329 mg) in DMF (3.9 mL) was stirred at rt overnight. A further 20 mg 5-(chloromethyl)-2-methoxypyridine was added and stirred for 2days. A further 100 mg 5-(chloromethyl)-2-methoxypyridine was added and stirred for 24 h. Water (20 mL) was added and the reaction mixture was extracted with EtOAc (3*20 mL). The combined organic layers were washed with brine (20 mL) and dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by column chromatography to give the desired compound (131 mg). LCMS: m/z 395.49 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.15-1.52 ppm (m, 4H) 1.71 (d, J=9.9 Hz, 2H) 2.05 (t, J=9.0 Hz, 2H) 2.50 (s, 3H) 3.16 (br. s., 1H) 3.49 (td, J=9.7, 4.3 Hz, 1H) 3.71-3.84 (m, 1H) 3.83 (s, 3H) 5.43 (s, 2H) 6.62 (d, J=8.6 Hz, 1H) 6.84 (d, J=4.8 Hz, 1H) 7.10 (dd, J=8.6, 2.1 Hz, 1H) 7.79 (d, J=1.8 Hz, 1H) 7.95 (s, 1H) 8.25 (d, J=4.6 Hz, 1H) 9.24 (d, J=7.0 Hz, 1H)

The synthetic route of 101990-70-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Payne, Andrew; Castro Pineiro, Jose Luis; Birch, Louise Michelle; Khan, Afzal; Braunton, Alan James; Kitulagoda, James Edward; Soejima, Motohiro; US2015/94328; (2015); 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. 45644-21-1, name is 2-Amino-6-chloropyridine. A new synthetic method of this compound is introduced below., Quality Control of 2-Amino-6-chloropyridine

To a solution of 6-chloropyridin-2-amine (50.0 g, 389 mmol) in DMF (700 mL) was added N-iodosuccinimide (105 g, 467 mmol). The brown solution was stirred at rt for 12 h. The mixture was poured into water (2.1 L) and filtered. The filter cake was washed with water (2*500 mL) and then dried under vacuum. Purification (FCC, SiO2; 5-20% EtOAc/petroleum ether) afforded the title compound (83 g, 75%) as a pink solid. MS (ESI): mass calcd. for C5H4ClIN2, 253.9; m/z found, 254.7 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.74 (d, J=8.0 Hz, 1H), 6.20 (d, J=8.0 Hz, 1H), 4.69 (br s, 2H).

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, 45644-21-1, 2-Amino-6-chloropyridine.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Gyuris, Mario; Laforteza, Brian Ngo; Lebold, Terry Patrick; Meyer, Stephen Todd; Ravula, Suchitra; Savall, Brad M.; Shireman, Brock T.; Wade, Warren Stanfield; Gerencser, Janos; (87 pag.)US2018/111933; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference 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.

Example 1; Preparation of N-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide; Step A: Preparation of 7-chlorothieno[3,2-b]pyridine; To a stirred solution of POCl3 (28.6 mL, 313 mmol) in 1,2-dichloroethane (200 mL) was added commercially available thieno[3,2-b]pyridin-7-ol (94.7 g, 626 mmol) as a powder in one portion. The reaction was stirred for 2 hours at reflux under N2. The mixture was concentrated, using toluene (3×100 mL) to azeotrope. The dark residue was resuspended in CH2Cl2 (1 L), and a saturated aqueous solution of NaHCO3 (500 mL) was carefully added. The mixture was stirred for 30 minutes until bubbling had ceased. The biphase was separated, and the aqueous was re-extracted with CH2Cl2 (500 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated, to obtain a brown oil, which crystallized upon standing (38.4 g, 71%). 7-Chlorothieno[3,2-b]pyridine has also been prepared using oxalyl chloride (WO 99/24440). 1H NMR (400 MHz, CDCl3) delta 8.61 (d, J=5 Hz, 1H), 7.80 (d, J=6 Hz, 1H), 7.60 (d, J=6 Hz, 1H), 7.29 (d, J=5 Hz, 1H).

According to the analysis of related databases, 69627-02-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Blake, James F.; Boyd, Steven; De Meese, Jason; Gaudino, John J.; Marlow, Allison L.; Seo, Jeongbeob; Thomas, Allen A.; Tian, Hongqi; US2007/197537; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 73781-91-6, Adding some certain compound to certain chemical reactions, such as: 73781-91-6, name is Methyl 6-chloronicotinate,molecular formula is C7H6ClNO2, 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 73781-91-6.

To a suspension of sodium hydride (55% dispersion in mineral oil, 852 mg, 20 mmol) in THF (27 mL) was added a solution of [3-(3-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methanol (3.68 g, 18 mmol) in THF (54 mL) at 0 C. and the reaction mixture warmed to room temperature over 30 min. Then a solution of methyl 6-chloronicotinate (3.35 g, 20 mmol) in THF (1.5 mL) was added dropwise at 0 C. and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then poured into aqueous sodium chloride (saturated) and the mixture was extracted with ethyl acetate. The combined organic layers were then washed with water and brine and then dried over sodium sulfate, filtered and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=7:3) afforded the title compound (4.1 g, 68%) which was obtained as a white solid. MS: m/e=343.1 [M+H]+.

According to the analysis of related databases, 73781-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Buettelmann, Bernd; Jakob-Roetne, Roland; Knust, Henner; Lucas, Matthew C.; Thomas, Andrew; US2009/143371; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1187190-69-7 , The common heterocyclic compound, 1187190-69-7, name is 6-Chloro-4-methoxynicotinonitrile, molecular formula is C7H5ClN2O, 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.

General procedure: General Procedure: An oven-dried test tube equippedwith a magnetic stir bar was charged with 2-chloroisonicotinonitrile (69 mg,0.5 mmol), Pd(OAc)2 (2.25 mg, 2 mol%), BINAP (9.38 mg, 3 mol%) , theamine if solid (1.0 mmol), and Cs2CO3 (228 mg, 1.0 mmol).The vessel was then sealed, evacuated, and backfilled with argon (this sequencewas carried out a total of three times). 1,4-dioxane (2.0 mL) and the amine ifliquid (1.0 mmol) via syringe was added successively under an argon atmosphere., and the solution was heated up to 80C for 4 h in an oil bath. The reactionmixture was allowed to cool to r.t. diluted with dichloromethane, and washed once each withwater and brine, dried over Mg2SO4, filtered, andconcentrated in vacuo. The crude product was then purified by silicagelchromatography mixture of pentane and Et2O or mixture of pentane andethyl acetate. The products were characterized by 1H NMR, 13CNMR and LC-MS.

The synthetic route of 1187190-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Shuo; Wang, Yaping; Sun, Chunxia; Li, Jingya; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng; Tetrahedron Letters; vol. 54; 25; (2013); p. 3233 – 3237;,
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. 55240-51-2, name is 2-Phenylisonicotinic acid. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

2-phenyl-4-carboxypyridine (3 g, 15 mmol) was refluxed overnight in MeOH (70 ml) and H2SO4 (4 ml). After evaporation of the solvent, water (100 ml) was added and the mixture was neutralized with saturated NaHCO3 solution. The aqueous phase was then extracted with CH2Cl2 (2×100 ml). The combined organic fractions were washed with water (100 ml), brine (50 ml) and dried over MgSO4. The crude compound was then flash chromatographed (SiO2, CH2Cl2) to afford 2.3 g (72%) of the titled compound as a colourless oil.

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, 55240-51-2, 2-Phenylisonicotinic acid.

Reference:
Patent; KONINKLIJKE PHILIPS ELECTRONICS N.V.; WO2007/4113; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 10592-27-5 ,Some common heterocyclic compound, 10592-27-5, molecular formula is C7H8N2, 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.

Step 2; A solution of Br2 (2.78 ml, 8.64 g, 54 mmole) in dry dichloromethane (40 ml) was added dropwise over a period of 1 h 45 min to a stirred and cooled (-10C) solution of 2.3-dihydro-1H-pyrrolo[2,3-b]pyridine (6.5 g,54 mmole) in a mixture of dry dichloromethane (60 ml) and pyridine (6 ml). The suspension was stirred at 0C for 2 hrs, poured into a mixture of NaHCO3 (120 ml) and saturated aqueous Na2S2O3 (15 ml) and extracted with a solution of ethyl acetate/methanol (3X200 ml). The organic layers were concentrated to afford 3.7 g of 5-bromo- 2,3-dihydro- 1H-pyrrolo[2,3-b]pyridine (2) after purification by flash chromatography using dichloromethane as eluent (35% yield). 1H NMR (400 MHz, DMSO-D6) delta ppm 2.98 ( t, J = 8.54 Hz, 2H ) 3.48 (t, J=8.55 Hz, 2H) 6.58 (bs, 1 H) 7.37(s,1 H) 7.71 (s,1 H)

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. 10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; EP2070928; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5470-70-2, 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. 5470-70-2, name is Methyl 6-methylnicotinate. A new synthetic method of this compound is introduced below.

0.471 g (1.0 equivalent) of N-bromosuccinimide and 64 mg (0.1 equivalent) of benzoyl peroxide are added to a solution of 0.4 g of the product obtained in the preceding Stage 1 in 15 ml of carbon tetrachloride. The solution is brought to reflux for 6 hours, then filtered and evaporated under reduced pressure. The residue is purified by chromatography on silica gel (dichloromethane/ethyl acetate: 95/5) to produce 0.262 g of the expected product. [ Yield: 43% MS: MH+ 231

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5470-70-2, Methyl 6-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Dublanchet, Anne-Claude; Compere, Delphine; Cluzeau, Philippe; Blais, Stephane; Denis, Alexis; Ducrot, Pierre; Courte, Karine; Descamps, Sophie; US2004/72871; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 4548-45-2, 2-Chloro-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, 4548-45-2, blongs to pyridine-derivatives compound. Recommanded Product: 2-Chloro-5-nitropyridine

To a stirring solution of compound 20 (5.0 g, 31.5 mmol) in acetic acid (50 ml) was added iron powder (8.8 g, 157.6 mmol) in small portion at room temperature, the reaction was exothermic and the temperature rise to 80C, end of added and kept the temperature at 40-50C and stirred for 2h. The reaction was filtered through celite and washed with little acetic acid, the filtrate was evaporated to dryness, adjusted pH=8 with saturated solution of sodium bicarbonate, extracted with dichloromethane (100 ml x 5). The combined organic phase was washed with brine, dried over Na2S04, filtered and concentrated to afford crude compound 84 (3.9 g, yield 96%) as a brown solid, used directly in next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4548-45-2, its application will become more common.

Reference:
Patent; SHANGHAI DE NOVO PHARMATECH CO LTD.; GAO, Daxin; YANG, Heping; YU, Yajun; WO2013/91502; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16133-25-8, Pyridine-3-sulfonyl chloride, 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, COA of Formula: C5H4ClNO2S, blongs to pyridine-derivatives compound. COA of Formula: C5H4ClNO2S

4-(a) tert-Butyl (tert-butoxycarbonyl{6-[(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)acetate To 14 ml of a methylene chloride solution containing 640 mg (3.60 mmol) of 3-pyridylsulfonyl chloride were added 1.20 g (3.56 mmol) oftert-butyl [(6-aminomethylpyridin-2-yl)tert-butoxycarbonylamino]acetate obtained by the same manner as in Reference example 1-(e) and 2.24 ml (16.2 mmol) of triethylamine, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, to the reaction mixture was added a 5percent aqueous potassium hydrogen sulfate solution, and the mixture was extracted with chloroform. The organic layer was successively washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (eluent; n-hexane:ethyl acetate=1:1–>1:2 (V/V)), and the fractions containing the objective material were concentrated under reduced pressure to obtain 1.45 g of the title compound as colorless oil. (Yield: 85percent) Mass spectrum (CI, m/z): 479 (M++1). 1H-NMR spectrum (CDCl3, delta ppm): 9.06 (d, J=2.2 Hz, 1H), 8.71 (dd, J=4.6, 1.5 Hz, 1H), 8.13-8.08 (m, 1H), 7.68 (d, J=8.2 Hz, 1H), 7.52 (dd, J=8.2, 7.4 Hz, 1H), 7.38-7.32 (m, 1H), 6.77 (d, J=7.4 Hz, 1H), 5.80 (t, J=5.1 Hz, 1H), 4.40 (s, 2H), 4.24 (d, J=5.1 Hz, 2H), 1.53 (s, 9H), 1.46 (s, 9H).

The synthetic route of 16133-25-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ube Industries, Ltd.; EP2476678; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem