Day: March 16, 2022

Adding a certain compound to certain chemical reactions, such as: 1201187-18-9, 6-Chloro-4-(trifluoromethyl)nicotinonitrile, 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, Recommanded Product: 6-Chloro-4-(trifluoromethyl)nicotinonitrile, blongs to pyridine-derivatives compound. Recommanded Product: 6-Chloro-4-(trifluoromethyl)nicotinonitrile

General procedure: To a stirred solution of 1Hpyrazole4carbaldehyde (1.00 g, 10.40 mmol) and 6bromo4methylnicotinonitrile (2.05 g, 10.40 mmol) in dioxane (15 mL) were added K2CO3 (4.31 g, 31.20 mmol). The resulting reaction mixture was degassed with nitrogen for 5 minutes then copper (I) iodide (0.59 g, 3.12 mmol) was added, followed by transN,N’dimethylcyclohexane1,2diamine (2.59 mL, 16.4 mmol). The resulting mixture was degassed again for 10 minutes and heated at 110 C for 1 h under microwave irradiation. The reaction mixture was cooled to ambient temperature, filtered through Celite and the organic layer was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep24 g, 2040% EtOAc/ nhexane) to obtain Intermediate 6 (1.15 g, 52.10%) as pale yellow solid. 1H NMR (300 MHz, DMSOd6) G^ppm 2.62 (s, 3 H), 8.10 (s, 1 H), 8.38 (s, 1 H), 8.95 (s, 1 H), 9.37 (s, 1 H), 9.98 (s, 1 H). LCMS (methodD), retention time 1.68 min, [M+H] 213.2.

The synthetic route of 1201187-18-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
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 1060814-91-6, name is Ethyl 2-(4-bromopyridin-2-yl)acetate. This compound has unique chemical properties. The synthetic route is as follows. name: Ethyl 2-(4-bromopyridin-2-yl)acetate

To a solution of compound 2-7 (1.3 g, 5.33 mmol, 1 eq) in dimethylformamide (2 mL) was added sodium hydride (533 mg, 13.32 mmol, 60% purity in mineral oil, 2.5 eq) at 0C under nitrogen atmosphere. The mixture was stirred at 0C for 20 minutes and methyl iodide (3.78 g, 26.63 mmol, 1.66 mL, 5 eq) was added. The mixture was stirred at 20C for 10 minutes. TLC (petroleum ether: ethyl acetate = 5:1) indicated the starting material was consumed completely and a new spot was formed. The mixture was poured into water (10 mL) and 1N hydrochloric acid (4 mL). The mixture was adjusted to pH = 8 with sodium bicarbonate solid and extracted with ethyl acetate (20 mLx3). The combined organic phase was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford compound 2-21 (1.44 g, 4.90 mmol, 91.92% yield) as yellow oil. LCMS: RT = 1.408 min, purity: 92.52 %, m/z 271.9,273.9 [M+H]+.1H NMR (CDCl3, 400 MHz): d 8.38 (d, J = 7.2 Hz, 1H), 7.48 (d, J = 2.0 Hz, 1H), 7.34 (dd, J1 = 7.2 Hz, J2 = 2.4 Hz, 1H), 4.17 (q, J = 9.6 Hz, 2H), 1.61 (s, 6H), 1.21 (t, J = 9.2 Hz, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 1060814-91-6.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; TRI-INSTITUTIONAL THERAPEUTICS DISCOVERY INSTITUTE, INC.; FUSHIMI, Makoto; SCALTRITI, Maurizio; HELLER, Daniel, Alan; MONTERRUBIO MARTINEZ, Carles; ARRUABARRENA ARISTORENA, Amaia; MEINKE, Peter, T.; FOLEY, Michael, Andrew; ASANO, Yasutomi; ASO, Kazuyoshi; TAKAHAGI, Hiroki; SHAMAY, Yosef; BASELGA TORRES, Jose, Manuel; SASAKI, Yusuke; MICHINO, Mayako; (271 pag.)WO2020/72892; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 135124-71-9, 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.135124-71-9, name is 5-(Hydroxymethyl)nicotinonitrile, molecular formula is C7H6N2O, molecular weight is 134.14, as common compound, the synthetic route is as follows.

To a stirred solution of 5-(hydroxymethyl)nicotinonitrile (3 g, 0.022 mol) in DCM (30 mL), 4M HC1 in l,4-dioxane (5 mL) was added and concentrated the mixture under vacuum. To the resulting residue, thionyl chloride (20 mL) was added and stirred the mixture at 60 C for 3h. After completion, the reaction was cooled to room temperature and diluted with toluene (150 mL) and filtered off the solid that precipitated out. The filtrate was diluted with DCM (200 mL) and washed with saturated sodium bicarbonate solution (200 mL). The organic layer was dried over sodium sulphate and concentrated to obtain 5-(chloromethyl)nicotinonitrile (Yield: 1.2 g, 35%) as yellow solid. 1H NMR (400 MHz, DMSO-d6, ppm): d 4.86 (s, 2H), 8.42 (s, 1H), 8.94 (d, / = 2.0 Hz, 1H), 8.99 (d, J = 2.0 Hz, 1H). Scheme -9: Synthesis of 3-(hydroxymethyl)-[l,l’-biphenyl]-2-carbonitrile

Statistics shows that 135124-71-9 is playing an increasingly important role. we look forward to future research findings about 5-(Hydroxymethyl)nicotinonitrile.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; D A, Jeyaraj; PENDYALA, Muralidhar; SIVANANDHAN, Dhanalakshmi; RAJAGOPAL, Sridharan; (233 pag.)WO2019/175897; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 51454-63-8, 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.51454-63-8, name is 2-(Hydroxymethyl)isonicotinonitrile, molecular formula is C7H6N2O, molecular weight is 134.14, as common compound, the synthetic route is as follows.

To a cooled solution of oxalyl chloride (13.2mL, 150mmol) in anhydrous DCM (86mL) under nitrogen atmosphere at -78C was added DMSO (21.2ml_ dropwise over 20 minutes. The mixture was stirred for 15 minutes at (-78C) before 2-hydroxymethyl-isonicotinonitrile (4.0g, 30 mmol) dissolved in anhydrous DCM (60mL) was added dropwise to the reaction mixture over 5 minutes. The reaction was stirred for 2 hrs at -78C maintaining a nitrogen atmosphere. A white solid precipitate formed and the temperature was raised to (-55C) and triethylamine (6.15mL, 450mmol) was added dropwise for over 15 minutes, cooling bath was removed allowing the mixture to warm to room temperature over 2 hrs. The mixture was diluted with DCM (400ml_) and washed with brine (2x 50mL). The aqueous phase was extracted with DCM (3x 50 ml_). The combined organic layers were combined and concentrated in vacuo. A buff white solid was isolated that was used without any further purification. Single peak in LC-MS analysis, (yield taken to be quantitative), m/z (LC-MS, ESP), RT=2.53mins, (M+H)=133.0.

Statistics shows that 51454-63-8 is playing an increasingly important role. we look forward to future research findings about 2-(Hydroxymethyl)isonicotinonitrile.

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2006/21801; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59782-90-0, 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 59782-90-0 as follows.

Under the protection of nitrogen, into the three-necked flask, add 53g benzylamine. Then use ice-bath to cool to 3 C. Then continue to add dropwise n-propanal 28g. Control dropwise addition time to 1h. Then add dropwise in batches 13g mass concentration of 10% KOH. Add dropwise 3 time. Then allow the layers to separate. To the organic phase, add 5g mass concentration of 10% KOH. Allow to stand overnight to prepare N-propylidenebenzylamine; Into a 250 ml four-necked flask, add 68g of the above-mentioned prepared N-propylidenebenzylamine. Then add 105 ml dichloromethane and triethylamine 47g. Stir and cool to 0 C, Then continue adding dropwise chloroacetyl chloride 57g. Control the dropwise addition at 1h. Then elevate temperature to 20 C. Continue reacting for 10 min; After the reaction is finished, the deionized water washing and the mass fraction of 10% hydrochloric acid pickling and the mass concentration is 10% of sodium hydroxide caustic wash, finally by reduced pressure distillation to remove the solvent, the reaction liquid prepared, subsequently heating the reaction liquid to column chromatography separation, collection acyl compound; In a 250 ml three-necked flask, add 23g dimethylformamide and 100 ml of 1,2-dichloromethane. Then stir and cool to 0 C. Then take 5.8g triphosgene. Use 50 ml of 1,2-dichloroethane to dissolve. Then add dropwise to the three-necked flask. Control the dropwise addition at 1h. After the completion of the dropwise addition, continue adding dropwise 4.4g of above-mentioned prepared acyl compound. Heat to 55 C and stir reaction for 1h; After the completion of reaction, washing with a large amount of deionized water and collecting the organic phase, for mass fraction of 10% sodium hydroxide solution to adjust the pH to 8.0, subsequently to its hierarchical collection of the organic layer, the solvent is removed by reduced pressure distillation column chromatography separation thereof, to collect colorless transparent crystal 2,3-dichloro-5-methylpyridine; 123.1g of nicotinic acid and 10 ml of 2,3-dichloro-5-methylpyridine were stirred and mixed; Elevate temperature to 55 C. Then add 270g phosphorus trichloride. At 70 C, enter chlorine gas for 2h. Continue heating to 150 C. Then 600 ml ethyl acetate and 20g sodium carbonate were added to the above-mentioned solution. Then continue reaction for 2h. Dry and concentrate and then dissolve in 100 ml toluene. Heat to 80 C and slowly enter phosgene. After reacting for 2h, the sodium carbonate is used to adjust the pH to 7.0, and separating an organic layer to dry the same, subsequently prepared desolution of the 2,3-chloro-5-chloromethyl pyridine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59782-90-0, its application will become more common.

Reference:
Patent; Changzhou University; Chen, Xingquan; (6 pag.)(2016);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 89364-04-5, name is 3-Bromo-4-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Bromo-4-nitropyridine

Example 1 (0052) Non-radioactive fluorination of 3-bromo-4-nitropyridine (3): 10 muL of 1 M tetrabutylammonium fluoride (TBAF) solution in THF (10 mumol, 0.5 eq.) was added to a solution of 3-bromo-4-nitropyridine (96%, Aurum Pharmatech, LLC) (20 mumol, 1 eq.) in 500 L of anhydrous dimethylsulfoxide (DMSO) in a 2 mL HPLC vial. The reaction was analyzed by HPLC (conditions A). Retention times: 3-bromo-4-nitropyridine (3)=10.83 min, 3-fluoro-4-nitropyridine=8.38, 3-bromo-4-fluoropyridine (6)=11.76 min. Retention times for the product matched within 0.05 min the reference standard. Identity of the product was confirmed by HR-MS (m/z M+ exp.: 174.9423, calc: 174.9433) and 1H, 13C and 19F NMR. Product amount was calculated from the area under the curve of the HPLC UV1 trace using a calibration curve.

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, 89364-04-5, 3-Bromo-4-nitropyridine.

Reference:
Patent; The University of Chicago; Brugarolas, Pedro; (35 pag.)US2017/355648; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 71777-70-3, 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.71777-70-3, name is Ethyl 4-ethoxypicolinate, molecular formula is C10H13NO3, molecular weight is 195.22, as common compound, the synthetic route is as follows.

To a solution of ethyl 4-ethoxypicolinate 198 (1 .6 g, 8.2 mmol) in concentrated H2SO4 (80 mL) was added NBS (2.7 g, 14.8 mmol). The reaction was stirred at room temperature overnight then quenched by addition of saturated aqueous NaHCCb (150 mL). The aqueous layer was extracted with DCM (3 x 130 mL) and the combined organic layers dried ( a2S04) and concentrated to give the title compound as a yellow solid (2.0 g, 91 %). 1H NMR (400 MHz, CDCI3) delta 8.67 (s, 1 H), 7.63 (s, 1 H), 4.94-4.40 (m, 2H), 4.29-4.23 (m, 2H), 1 .54-1 .51 (0853) (m, 3H), 1 .46-1 .42 (m, 3H); LCMS-C: RT 2.59 min; m/z 274.0, 276.0 [M+H]+

Statistics shows that 71777-70-3 is playing an increasingly important role. we look forward to future research findings about Ethyl 4-ethoxypicolinate.

Reference:
Patent; CTXT PTY LTD; BERGMAN, Ylva Elisabet; FOITZIK, Richard Charles; MORROW, Benjamin Joseph; CAMERINO, Michelle Ang; WALKER, Scott Raymond; LAGIAKOS, H. Rachel; FEUTRILL, John; STEVENSON, Graeme Irvine; STUPPLE, Paul Anthony; (222 pag.)WO2016/34673; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem