Day: June 10, 2021

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

Synthetic Route of 884495-14-1 ,Some common heterocyclic compound, 884495-14-1, molecular formula is C7H7BrN2O3, 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.

DMF-DMA (600 mL) was slowly added to a stirred and heated (80 C) solution of 5-bromo-2- methoxy-4-methyl-3-nitropyridine (134 g, 0.54 mol) in DMF (1.1 L). After addition, the mixture was heated at 95 C for 5 h, at which time TLC indicated the reaction had gone to completion. The mixture was cooled to room temperature and poured into ice-cold water (3 L). The resulting red solid was collected by filtration, washed with water, and dried under reduced pressure to give the title compound (167 g, 100% yield) as red solid. 1H NMR (400 MHz, DMSO-d6): 6 8.24 (s, 1 H), 7.05 (d, J= 13.6 Hz, I H), 7.05 (d, J= 13.6 Hz, 1 H), 4.80 (d, J = 13.2 Hz, 1 H), 3.88 (s, 3 H), 2.90 (s, 6 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-14-1, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; BELLON, Steven, F.; BURDICK, Daniel, J.; COTE, Alexandre; CRAWFORD, Terry; DAKIN, Les, A.; HEWITT, Michael, Charles; HSIAO-WEI TSUI, Vickie; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F. Anthony; TANG, Yong; TAYLOR, Alexander, M.; WANG, Shumei; (128 pag.)WO2016/77380; (2016); 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

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

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

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

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

Related Products of 156118-16-0, 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. 156118-16-0, name is 3-Amino-6-bromo-4-methylpyridine, molecular formula is C6H7BrN2, 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.

Step 2 [0611] To a suspension 6-bromo-4-methylpyridin-3 -amine (XV) (186 g, 994 mmol, 1.00 eq) and KOAc ( 1 15 g, 1.17 mol, 1.18 eq) in CHC13 (3.50 L) was added Ac20 (405 g, 3.97 mol, 3.99 eq) and the suspension was stirred at 25C for 1 h and then heated at 60-70C to reflux for an additional 2 h. After cooling the suspension to 25C, isopentyl nitrate (233 g, 1.99 mol, 2.00 eq) and 18-crown-6 (21 g, 79.5 mmol, 0.08 eq) was added and the suspension heated to reflux for 12 h. After cooling to 25C, the suspension was filtered and the filtrate was concentrated under reduced pressure to yield a residue that was treated with a suspension of potassium carbonate (450 g) in a solution of methanol and water (450 mL) at 0C for 3 h. The suspension was concentrated under reduced pressure to yield a residue that was extracted with EtOAc (1000 mL x 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 5-bromo-lH-pyrazolo[3,4-c]pyridine (XVI) (200 g, crude) as yellow solid. The crude product was used for the next step without any purification. NMR (DMSO- tf, 400 MHz) delta ppm 7.96 (s, 1H), 8.15 (s, 1H), 8.86 (s, 1H); ESIMS found for C6H4BrN3 mlz 198.3 (M+H).

According to the analysis of related databases, 156118-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (261 pag.)WO2017/23984; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59786-31-1 ,Some common heterocyclic compound, 59786-31-1, molecular formula is C7H6BrNO2, 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 115a. To a solution of methyl 3-bromoisonicotinate (0.2 g, 0.93 mmol, 1.0 equiv) in Dioxane (10 mL) was added benzenethiol (0.204 g, 1.85 mmol, 2.0 equiv), KOAc (0.184 g, 1.876 mmol, 2.0 equiv) and resulting reaction mixture purged with N2 gas for 10 minute, followed by the addition of Pd2(dba)3 (0.042 g, 0.046 mmol. 0.05 equiv), Xanthphose (0.026 g, 0.046 mmol, 0.05 equiv) and resulting reaction mixture). The resulting reaction mixture was heated at 90 C. for overnight. Product formation was confirmed by LCMS. After the completion of reaction, the mixture was filtered through celite bed, washed with ethyl acetate (100 mL). Filtrate was concentrated under reduced pressure. The crude product obtained was purified by flash chromatography (20% ethyl acetate hexane as an eluent) to obtain methyl 3-(phenylthio)isonicotinate (0.100 g, 44.4% Yield) as yellow oil. (0939) LCMS 246.1 [M+H]+ (0940) 1H NMR (400 MHz, DMSO-d6) delta 8.92 (br. s., 1H), 8.76-8.56 (m, 2H), 7.50 (s, 1H), 7.48-7.40 (m, 2H), 7.40-7.29 (m, 2H), 5.14-5.04 (m, 1H), 4.21 (br. s., 1H), 4.03 (d, J=2.6 Hz, 2H), 2.87 (br. s., 1H), 2.79 (d, J=14.5 Hz, 1H), 2.67 (br. s., 1H).

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. 59786-31-1, Methyl 3-bromoisonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Praxis Biotech LLC; ALFARO, Jennifer; BELMAR, Sebastian; BERNALES, Sebastian; PUJALA, Brahmam; PANPATIL, Dayanand; BHATT, Bhawana; US2019/185451; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 149489-32-7, 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 149489-32-7, name is 2-(Chloromethyl)-3-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 182; N-[6-Cyano-9-(3-fluoro-pyridin-2-ylmethyl)-2,3,4,9-tetrahydro-lH-carbazol-3-yl]- isobutyramideSuspend sodium hydride (60% suspension in mineral oil, 114 mg, 1.64 mmol) in dimethylformamide (7 mL) and cool to 0 0C. Add a solution of N-(6- cyano-2,3,4,9-tetrahydro-lH-carbazol-3-yl)-isobutyramide (Preparation 3) (385 mg, 1.37 mmol) in dimethylformamide (3.5 mL). After several minutes, warm the reaction to room temperature, and stir for 30 min, after which time add 2- chloromethyl-3-fluoro-pyridine (Preparation 60). Stir the reaction overnight and then dilute with ethyl acetate (100 mL). Wash the reaction mixture sequentially with brine (3 x 75 mL), water (75 mL), and brine (75 mL). Separate the organic layer, dry over magnesium sulfate, filter, and concentrate under reduced pressure. Purify using flash chromatography [silica gel, gradient from 0: 100 to 20:80 (90: 10: 1 EPO dichloromethane:methanol:concentrated ammonium hydroxide) :dichloromethane] to provide 184 mg (38%) of the title compound as an off-white solid, m.p. = 213- 216 0C; MS: m/z 391 [C23H23FN4O + I]+; 1H NMR (300 MHz, DMSO-J6): delta 8.29- 8.31 (m, IH), 7.92 (d, /= 1.2 Hz, IH), 7.84 (d, / = 7.6 Hz, IH), 7.71-7.78 (m, IH), 7.58 (d, / = 8.5 Hz, IH), 7.38-7.44 (m, 2H), 5.56 (s, 2H), 3.99-4.04 (m, IH), 2.73- 3.00 (m, 3H), 2.49-2.55 (m, IH), 2.37 (septet, J= 6.8 Hz, IH), 1.96-2.00 (m, IH), 1.76-1.83 (m, IH), 1.01 (d, /= 6.8 Hz, 6H).

According to the analysis of related databases, 149489-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/2181; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem