Tag: M.W:200-300

Synthetic Route of 17282-40-5, 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.17282-40-5, name is 1-(2-Ethoxy-2-oxoethyl)pyridin-1-ium bromide, molecular formula is C9H12BrNO2, molecular weight is 246.1011, as common compound, the synthetic route is as follows.

General procedure: Mixture of ethyl acetoacetate(1, 211 mg, 0.153 mmol), hydrazine (2, 81 mg, 0.153), 7-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde (4a, 406 mg,0.153 mmol), 1-(2-ethoxy-2-oxoethyl)pyridinium ylide (4, 272mg, 0.153 mmol), 0.1 equivalents of trimethylamine (16 mg,0.015 mmol) in15 mL EtOH were refluxed in a pre-heated oilbath (80 C) under the blanket of nitrogen for 30 min till the completion of reaction (TLC, 20 % dicholromethane in hexanes; Rf = 0.3). The reaction mixture was diluted with dichloromethane (10 mL) and the organic solution was washed with water (20 mL) and brine (20 mL) and dried over anhydrousNa2SO4. Column chromatographic purification on silica gelwith increasing amount of dichlormethane in hexanes provided 8a as a free flowing solid in about 88 % yield. Analytical samples were obtained through from the recrystallization in EtOH.

Statistics shows that 17282-40-5 is playing an increasingly important role. we look forward to future research findings about 1-(2-Ethoxy-2-oxoethyl)pyridin-1-ium bromide.

Reference:
Article; Tangeti, Venkata Swamy; Vasundhara; Satyanarayana; Pavan Kumar, Kaja Srinivas; Asian Journal of Chemistry; vol. 29; 7; (2017); p. 1525 – 1532;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53937-02-3, 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. 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone. A new synthetic method of this compound is introduced below.

c) 4-(Benzyloxy)- 1 -( 1 -(2-(pyrrolidin- 1 -yl)ethyl)- lNo.-indazol-5-yl)pyridin-2( lNo.)-one; Chemical Formula C25H26N4O2Exact Mass 414 21 Molecular Weight 414 5 [0081] A suspension of 5-bromo-l-(2-(pyrrolidin-l-yl)ethyl)-lH-indazole (0 21 g, 0.70 mmol) in 1,4-dioxane (10 mL) stirred under nitrogen was treated sequentially with 4- (benzyloxy)pyridin-2(li/)-one (0.14 g, 0.70 mmol), trans- 1,2-diaminocyclohexane (0.03 mL, 0.2 mmol), CuI (28 mg, 0.15 mmol) and K2CO3 (0.19 g, 1 4 mmol). After stirring overnight at 1100C, the mixture was allowed to cool to room temperature, diluted with CH2Cl2, washed with brine, dried over Na2SO4, filtered and concentrated to dryness. Purification by flash column chromatography (silica gel, CH2Cl2/Me0H, 95:5 to 90: 10) gave the title compound (21 mg, 7%) as an off-white powder 1H NMR (500 MHz, DMSO-J6) delta 8.03 (s, IH), 7.66 (d, J = 1.4 Hz, IH), 7.53 (d, J = 8.8 Hz, IH), 7.43-7.36 (m, 6H), 7.28 (d, J = 7.5 Hz, 1 H), 6.09-6.06 (m, 2H), 5.06 (s, 2H), 4.58-4.55 (m, 2H), 3.03 (br m, 2H), 2 61 (br m, 4H), 1.81 (br m, 4H); ESI MS m/z 415 [M + H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53937-02-3, 4-Benzyloxy-2-(1H)-pyridone, and friends who are interested can also refer to it.

Reference:
Patent; AMR TECHNOLOGY, INC.; WO2008/86404; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65550-77-8, Adding some certain compound to certain chemical reactions, such as: 65550-77-8, name is 2-Bromo-5-chloro-3-methylpyridine,molecular formula is C6H5BrClN, 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 65550-77-8.

10201] Under nitrogen condition, 2-bromine-3-methyl-5-chioropyridine (400.00 mg, 1.94 mmol, 1.00 eq), WX1313-3-1 (465.61 mg, 2.32 mmol, 1.20 eq), sodium tert-butoxide (372.35 mg, 3.87 mmol, 2.00 eq), 1,1?-binaphthyl-2,2?-bis (diphenylphosphino) (241.26mg, 387.47 tmol, 0.20 eq) and tris(dibenzylideneacetone)dipalladium (177.40 mg, 193.73 tmol, 0.10 eq) were dissolved in anhydrous methylbenzene (10.00 mE). The mixture was stirred at 90 C. for 12 h. After reaction, the reaction liquid was dried by rotary evaporation to obtain the crude. The crude was purified by column chromatography (ethyl acetate: petroleum ether=1.-20%) to obtain WXO11-1. ?H NMR (400 MHz, CDC13) oeppm: 7.96 (d, J=2.00 Hz, 1H), 7.22 (s, 1H), 4.17-4.06 (m, 1H), 3.68- 3.61 (m, 1H), 3.58-3.46 (m, 2H), 3.41-3.31 (m, 1H), 2.07 (s, 3H), 1.99-1.86 (m, 1H), 1.84-1.67 (m, 2H), 1.65-1.60 (m, 1H), 1.59 (s, 9H).

According to the analysis of related databases, 65550-77-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHENZHEN SALUBRIS PHARM CO LTD.; Wu, Chengde; Yan, Jie; Xu, Wenjie; Yu, Tao; Li, Ning; Chen, Shuhui; US2018/305346; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 669066-93-7, 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 669066-93-7 as follows.

To a solution of the compound [172-1] obtained in the process (1) (426 mg) in ethylene glycol (2.1 mL) was added hydrazine monohydrate (197 muL) at room temperature, and then the reaction mixture was stirred at 140C for 23 hours. After cooling to room temperature, to the reaction mixture was added water, and extracted with a mixed solution of chloroform/isopropanol (volume ratio 10/1). The obtained organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (275 mg) as a yellow solid. 1H-NMR (400 MHz, CDCl3) delta: 10.17 (1H, br), 8.65 (1H, d, J = 1.7 Hz), 8.31 (1H, s), 8.04 (1H, s). ESI-MS found: 198 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,669066-93-7, its application will become more common.

Reference:
Patent; Sato Pharmaceutical Co., Ltd.; NAGAI Keita; NAGASAWA Koh; TAKAHASHI Hirobumi; BABA Motoaki; FUJIOKA Shinichi; KONDOH Eri; TANAKA Kenichi; ITOH Yoshiki; EP2669270; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 885500-55-0, Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, 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, 885500-55-0, blongs to pyridine-derivatives compound. COA of Formula: C10H9ClN2O2

Preparation 14 To a solution of ethyl 4-chloro-1H-pyrrolo[2,3-b]-pyridine-5-caboxylate (2 g) in DMF (20 mL) was added NaH (60% dispersion in oil, 427 mg) at 5C. After the reaction mixture was stirred at ambient temperature for 1 hour, [2-(chloromethoxy)ethyl]-(trimethyl)silane (1.72 mL) was added, and the mixture was stirred at ambient temperature for additional 2 hours. After the reaction mixture was diluted with EtOAc (50 mL), the solution was washed with saturated NaHCO3 aqueous solution (50 mL) and brine (50 mL) successively. After the organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane) to afford ethyl 4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-caboxylate (2. 91 g) as a colorless viscous liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,885500-55-0, its application will become more common.

Reference:
Patent; Astellas Pharma Inc.; EP2123651; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 886365-28-2, Methyl 5-bromo-2-chloroisonicotinate, 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: Methyl 5-bromo-2-chloroisonicotinate, blongs to pyridine-derivatives compound. name: Methyl 5-bromo-2-chloroisonicotinate

To a mixture of methyl 5-bromo-2-chloroisonicotinate (10 g, 39.9 mmol) and Pd(Ph3P)4(4.61 g, 3.99 mmol) in THF (100 mL) was added trimethylaluminum (26.0 mL, 51.9 mmol) at 25C. The mixture was then heated to and stirred at 80 C for 6 h. Water (5 mL) was added toquench the reaction and the mixture was concentrated in vacuum. The residue was purified by flash silica gel chromatography (eluting with ethyl acetate/pet. ether gradient) to give methyl 2- chloro-5-methylisonicotinate as a colorless oil. MS: 186 (M + 1). ?HNMR (400 MHz, CDC13) 8.29 (s, 1H), 7.70 (s, 1H), 3.91 (s, 3H), 2.49 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,886365-28-2, Methyl 5-bromo-2-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CTXT PTY. LTD.; MACHACEK, Michelle, R.; WITTER, David, J.; REUTERSHAN, Michael Hale; ALTMAN, Michael, D.; STUPPLE, Paul Anthony; (67 pag.)WO2019/94311; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 189278-27-1, 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. 189278-27-1, name is 2-Bromo-6-(trifluoromethyl)pyridine, molecular formula is C6H3BrF3N, 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 30 (3aR,4R,6aS)-2-[6-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-ol (3aR,4R,6aS)-Octahydrocyclopenta[c]pyrrol-4-ol (1.65 g, 12.97 mmol) from Example 29, 2-bromo-6-(trifluoromethyl)pyridine (3.66 g, 16.22 mmol) and triethylamine (7.23 mL, 51.9 mmol) were combined in ethanol (7.23 mL). The reaction was heated at 80 C. for 24 hours and the solvent was concentrated in vacuo. The resulting residue was purified by silica gel chromatography using 0-40% ethyl acetate/hexane as eluent to give the title compound and the title compound of Example 31: 1H NMR (500 MHz, pyridine-d5) delta ppm 7.47 (t, J=7.9, 1H), 6.94 (d, J=7.2, 1H), 6.53 (d, J=8.6, 1H), 6.38 (d, J=4.1, 1H), 4.47-4.38 (m, 1H), 4.12 (dd, J=11.0, 4.3, 1H), 3.70-3.63 (m, 1H), 3.53 (t, J=10.0, 1H), 3.38 (dd, J=10.4, 4.6, 1H), 2.80-2.73 (m, 1H), 2.72-2.64 (m, 1H), 1.97-1.74 (m, 3H), 1.64-1.56 (m, 1H); MS (ESI+) m/z 273 (M+H)+.

According to the analysis of related databases, 189278-27-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; US2011/294854; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15862-37-0, 2,5-Dibromo-3-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, Product Details of 15862-37-0, blongs to pyridine-derivatives compound. Product Details of 15862-37-0

Step 1: Methyl 4-(5-bromo-3-nitropyridin-2-yl)benzoate To a mixture of 2,5-dibromo-3-nitropyridine (2.00 g, 7.09 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (1.28 g, 7.09 mmol) Pd(dppf)C12 (0.36 g, 0.50 mmol) in THF (30 mL) was added tripotassium phosphate (3M in water) (7.09 mL, 21.3 mmol). The reaction mixture was purged with N2 (3x) and then stirred at 80 C for 3 h. The aqueous layer was separated. The organic layer dried with Na2SO4, filtered through a small plug of Celite washing with EtOAc and concentrated. The crude residue waspurified using ISCO silica gel chromatography (120 g column, gradient from 0% to 50% EtOAc/CH2C12) to give the title compound (1.64 g, 69%) as a white solid. Step 1: 5-Bromo-2-(2-fluoro-5-methanesulfonylphenyl)-3-nitropyridineFollowing procedures analogous to those described for methyl 4-(5-bromo-3-nitropyridin-2-yl)benzoate, 2-(2-fluoro-5 -methanesulfonylphenyl)-4,4,5 ,5 -tetramethyl1,3 ,2-dioxaborolane (500 mg, 1.66 mmol) was converted to the title compound (325 mg,52%). ?H NMR (500MHz, CDC13) oe 9.02 (d, J=2.0 Hz, 1H), 8.58 (d, J=2.0 Hz, 1H), 8.34(dd, J6.5, 2.4 Hz, 1H), 8.10 (ddd, J8.7, 4.7, 2.4 Hz, 1H), 7.34 (dd, J=9.4, 8.8 Hz, 1H),3.15 (s, 3H); LCMS (M+H) = 375; HPLC RT = 1.977 mm (Column: Chromolith ODS S54.6 x 50 mm; Mobile Phase A: 10:90 MeOH:water with 0.1% TFA; Mobile Phase B:90:10 MeOH:water with 0.1% TFA; Temperature: 40 C; Gradient: 0-100% B over 4 mm; Flow: 4 mL/min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15862-37-0, 2,5-Dibromo-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 17282-03-0 ,Some common heterocyclic compound, 17282-03-0, molecular formula is C6H5BrClN, 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.

Synthesis 53 [5-(2-Chloro-5-methyl-pyridi -3-yl)-thiazol-2-yl]-propyl-carbamic acid tert-butyl ester 3-tert-Butyl-1-propyl-1-[5-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-thiazol-2-yl]-urea (1 mmol, 0.37 g) 2-chloro-3-bromo-5-methylpyridine (1 mmol, 0.20 g), potassium carbonate (2 mmol, 0.27 g) and bis(triphenylphosphine) palladium(ll)dichloride (0.050 mmol, 0.035 g) were weighed into a microwave vial and treated with dioxane (1.5 mL) and water (0.5 mL). The reaction mixture was heated at 130 C for 15 minutes in a microwave reactor. The reaction mixture was diluted with water (40 mL), extracted with DCM (2×30 mL) and passed through a phase separation cartridge. The organics were evaporated to a brown oil. This was purified by flash column chromatography 1 :9 ethyl acetate cyclohexane to yield the title compound as a pale yellow oil. LCMS, analytical method 2, TR=6.22 mins, 70%, Ml+H=368.

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. 17282-03-0, 3-Bromo-2-chloro-5-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHARLES, Mark David; BROOKFIELD, Joanna Lola; EKWURU, Chukuemeka Tennyson; STOCKLEY, Martin Lee; WO2015/25172; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 52833-94-0, 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 52833-94-0 as follows.

Step 2: 5-Bromo-3-(3-(difluoromethyl)-1 ,2,4-oxadiazol-5-yl)pyridin-2-amine To a stirring suspension of 2-amino-5-bromonicotinic acid (500 mg, 2.304 mmol) in DCM (11.5 ml) was added 1-chloro-N,N,2-trimethyl-1-propenylamine (Ghosez’s reagent) (0.366 ml, 2.76 mmol). The reaction mixture was left stirring for 1.5 hrs. 2,2-Difluoro-N’- hydroxyacetimidamide (step 1) (507 mg, 4.61 mmol) was added followed by DIPEA (0.805 ml, 4.61 mmol) and the mixture was stirred overnight. T3P (4.04 ml, 6.91 mmol) was added and the mixture was heated using microwave radiation for 135 mins at 100C. The mixture was added to water (100ml) and the product extracted into EtOAc (2 x 90ml). The organic phase was washed with brine, dried over MgS04 and concentrated to dryness. The crude product was purified by flash column chromatography, eluting with 0-10% gradient of (2M NH3 in MeOH) in DCM on a 24g Si-column to afford the title compound; LCMS: Rt = 1.11 mins; MS m/z 291.4 [M+H]+; Method 2minl_owpHv01 1H NMR (400 MHz, DMSO-d6) delta 8.43 (1 H, d), 8.39 (1 H, d), 7.55 (2H, br s), 7.47 (1 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,52833-94-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; WO2015/162456; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem