Month: March 2022

Reference of 1149-24-2, 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.1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, molecular formula is C13H17NO4, molecular weight is 251.28, as common compound, the synthetic route is as follows.

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

The chemical industry reduces the impact on the environment during synthesis 1149-24-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 153747-97-8, 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.153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, molecular weight is 342.23, as common compound, the synthetic route is as follows.

Under nitrogen protection,Tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (202 mg, 0.59 mmol),N,N-bis(tert-butoxycarbonyl)-3-(1-(2,5-dichlorophenyl)ethoxy)-5-(4,4,5,5-tetramethyl-1,3) ,2-Dioxaborolan-2-yl)pyridin-2-amine (300 mg, 0.49 mmol) andCesium carbonate (320mg, 0.98mmol)Ethylene glycol dimethyl ether/water (10 mL/1 mL)Pd(dppf)Cl2.CH2Cl2 (40 mg, 0.05 mmol) was added to the mixture.The reaction solution is heated to 90C.After stirring overnight, cool to room temperature and filter through celite. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography on silica gel (PE/EtOAc (v/v) = 5/1) to give the title compound as a yellow oil (250 mg, 68%).

Statistics shows that 153747-97-8 is playing an increasingly important role. we look forward to future research findings about tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wang Tingjin; (104 pag.)CN104650049; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89809-65-4, 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.89809-65-4, name is Methyl 6-Cyanopyridine-3-carboxylate, molecular formula is C8H6N2O2, molecular weight is 162.1454, as common compound, the synthetic route is as follows.

To a solution of methyl 5-(3-chlorobenzyl)pyridin-2-amine (0.262 g, 1 .2 mmol) in toluene (7 ml_) was added trimethylaluminum (0.6 ml_,1 .2 mmol, 2 M in toluene) at room temperature under argon. The reaction mixture was stirred at room temperature for 1 h before a solution of methyl 6-cyanonicotinate (0.162 g, 1 mmol) in toluene (2 ml_) was added. Reaction mixture was stirred at 100 0 C for 2 h under argon. The reaction solution was cooled to room temperature and quenched with methanol (5 ml_) and 1 N hydrochloric acid aqueous (5 ml_). The volatiles were concentrated, and the aqueous phase was extracted with dichloromethane (1 00 ml_ x 2). The combined organic layers were washed with brine (1 00 ml_), dried over sodium sulfate, filtered and concentrated. The crude sample was dissolved in minimal A/,A/-dimethylformamide and purified v/a prep-HPLC (Boston C18 21 *250 mm 10 pm column. The mobile phase was acetonitrile/0.01 % aqueous trifluoroacetic acid) to give A/-(5-(3-chlorobenzyl)pyridin-2-yl)-6-cyanonicotinamide (70 mg, 0.20 mmol, 20.8%) as a white solid. 1 H NMR (500 MHz, Dimethylsulfoxide-c/g) d 1 1 .33 (s, 1 H), 9.22 (d, J = 1 .3 Hz, 1 H), 8.53 (dd, J = 4.3, 2.5 Hz, 1 H), 8.36 (d, J = 2.0 Hz, 1 H), 8.20 (d, J = 8.0 Hz, 1 H), 8.12 (d, J = 8.5 Hz, 1 H), 7.75 (dd, J = 4.3, 2.5 Hz, 1 H), 7.35 – 7.32 (m, 2H), 7.28-7.23 (m, 2H), 3.99 (s, 2H); LCMS (ESI) m/z: 349.0 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 89809-65-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1116136-63-0 ,Some common heterocyclic compound, 1116136-63-0, molecular formula is C7H4ClN3O2, 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.

Into a 250 ml 3-necked roundbottom flask, was placed a solution of 5-chloro-3-nitro-1H- pyrrolo[3,2-b]pyridine (1.1 g, 5.56 mmol, 1.00 equiv) in 1,4-dioxane (30 ml). To this was added HCl (6mol/L) (15 ml, 90 mmol, 16.00 equiv). This was followed by the addition of a solution of Fe (2.5 g, 44.64 mmol, 8.00 equiv) in MeOH (50 ml). The resulting solution was allowed to react, with stirring, for 3 hours while the temperature was maintained at reflux in a bath of oil. A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was diluted with H2O. Adjustment of the pH to 7-8 was accomplished by the addition of Na2CO3. The resulting solution was extracted three times with 100 ml of EtOAc and the organic layers combined and dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 1.3 g (crude) of 5-chloro-1H-pyrrolo[3,2-b]pyridin-3-amine as a black solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1116136-63-0, its application will become more common.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2009/23844; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 550347-54-1 ,Some common heterocyclic compound, 550347-54-1, molecular formula is C6H5ClIN, 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 stirred solution of 2-chloro-5-iodo-4-methyl-pyridine (23. Og, 90.909mmol, 1 eq) in 1 ,2-dichloroethane (230ml_) was added NBS (24.3g, 136mmol, 1 .5eq) followed by addition of AIBN (6.0g, 36.4mmol, 0.4eq) at room temperature in dark. Resulting reaction mixture was heated at 80C for 16 hours. After maximum consumption of starting material, reaction mixture was cooled to room temperature and quenched with water (50ml_), extracted with DCM (3x50ml_). Combined organic phase was washed with brine (50ml_), dried over anhydrous Na2S04 and concentrated under reduced pressure to get dark brown semi solid (20g, crude). Crude of title compound was used as such for next reaction. LC-MS (m/z): No ionisation.

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. 550347-54-1, 2-Chloro-5-iodo-4-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ZOETIS LLC; MENON, Sanjay; SHEEHAN, Susan M.K.; VAILLIANCOURT, Valerie A.; WO2014/39484; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884495-01-6, Adding some certain compound to certain chemical reactions, such as: 884495-01-6, name is 4-Bromo-5-fluoro-2-hydroxypyridine,molecular formula is C5H3BrFNO, 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 884495-01-6.

A mixture of 4-bromo-5-fluoropyridin-2-ol (442 mg, 2.31 mmol), ethyl 2-iodo-4-methylpentanoate (937 mg, 3.47 mmol) and K2CO3 (958 mg, 6.94 mmol) in MeCN (10 mL) was stirred at 85 C. overnight and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column (pet. ether_EtOAc=4:1) to give the desired product ethyl 2-(4-bromo-5-fluoro-2-oxopyridin-1(2H)-yl)-4-methylpentanoate as a colorless oil (402 mg). Yield 52% (97% purity, UV=214 nm, ESI 334.0 (M+H)+).

According to the analysis of related databases, 884495-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Morphic Therapeutic, Inc.; Bursavich, Matthew G.; Troast, Dawn M.; Harrison, Bryce A.; Lippa, Blaise S.; Rogers, Bruce N.; Konze, Kyle D.; Gerasyuto, Aleksey I.; Day, Tyler; Lin, Fu-Yang; Hahn, Kristopher N.; Svensson, Mats A.; Kim, Byungchan; Zhong, Cheng; Lugovskoy, Alexey A.; Sosa, Brian; (263 pag.)US2019/315692; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 865664-04-6, Adding some certain compound to certain chemical reactions, such as: 865664-04-6, name is 2-Chloro-3-cyclopropylpyridine,molecular formula is C8H8ClN, 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 865664-04-6.

Palladium(ll) acetate (61 mg, 0.27 mmol) and di-fert-butyl[3,4,5,6-tetramethyl-2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane (130 mg, 0.27 mmol) were added to a mixture of C6 (615 mg, 4.00 mmol), C5 (1 .0 g, 2.6 mmol) and cesium carbonate (2.6 g, 8.0 mmol) in 1,4-dioxane (25 mL). The reaction mixture was stirred at 120 C under microwave irradiation for 5 hours, then diluted with ethyl acetate (50 mL) and filtered. After removal of solvents in vacuo, the residue was purified via silica gel chromatography (Gradient: 0% to 25% ethyl acetate in petroleum ether) to provide the product as a yellow gum. Yield: 900 mg, 1 .8 mmol, 69%. LCMS m/z 494.1 [M+H]+. 1 H NMR (400 MHz, CDCl3) delta 8.02 (dd, J=4.8, 1.8 Hz, 1 H), 7.30 (dd, J=7.4, 1.8 Hz, 1 H), 7.11 -7.14 (m, 1 H), 7.08-7.10 (m, 2H), 7.01 (dd, J=7.5, 4.8 Hz, 1 H), 5.51 (AB quartet, JAB=9.3 Hz, DeltanuAlphaBeta=3.8 Hz, 2H), 3.74-3.80 (m, 2H), 3.08 (s, 3H), 2.18 (s, 3H), 2.16-2.24 (m, 1 H), 1.70 (s, 3H), 1.00-1.06 (m, 4H), 0.74-0.79 (m, 2H), 0.03 (s, 9H).

According to the analysis of related databases, 865664-04-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; GRAY, David Lawrence Firman; GREEN, Michael Eric; HENDERSON, Jaclyn Louise; LEE, Chewah; MENTE, Scot Richard; O’NEIL, Steven Victor; ROGERS, Bruce Nelsen; ZHANG, Lei; WO2014/207601; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1049744-89-9 ,Some common heterocyclic compound, 1049744-89-9, molecular formula is C6H7ClF3N3, 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.

A mixture of 5-(4-methoxyphenyl)-1,2,4-oxadiazole-3-carbaldehyde (500 mg, 2.40 mmol) and2-hydrazino-5-(trifluoromethyl)pyridine hydrochloride(877 mg, 2.52 mmol) in MeCN (10 n) was stirred atRT for 3 h. The resulting suspension was diluted with water (10 mL) and filtered. The filter cake was washed with water (10 mL) and dried overnight invacuum oven (50 C, 20 mbar) to give the title compound as a brown solid (630 mg, 1.73 mmol, 72%,Ca. 90:10 mixture of stereoisomers).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1049744-89-9, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; KENNEDY, Jason W. J.; VON MORGENSTERN, Sascha; (37 pag.)WO2016/135062; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 853909-08-7, 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 853909-08-7, name is 5-Ethynyl-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Under argon, to a solution containing 3-aminoquinuclidine bishydrochloridesalt 2 (212 mg, 1.00 mmol) and 1H-imidazole-1-sulfonyle azide 1 (232 mg, 1.10 mmol) in MeOH (6 mL) wasportion wise added K2CO3 (415 mg, 3.00 mmol) and next a catalyticamount of CuSO4, 5H2O (25 mg, 0.10 mmol). The reaction mixturewas stirred at room temperature for 6 h and then concentratedunder reduced pressure. The crude solid was solubilized in Et2O(10 mL), filtered and the precipitate washed with an additionalamount of Et2O (10 mL). The combined organic layers were reducedunder reduced pressure and the (R) intermediate 3a used in thenext step. After addition of MeOH (6 mL), the desired terminalalkyne 4 (1.00 mmol) and next CuSO4, 5H2O (25 mg, 0.10 mmol),sodium ascorbate (40 mg, 0.20 mmol) were successively added. Thereaction mixturewas stirred for 12 h at room temperature. Volatileswere evaporated under reduced pressure and the residue purifiedby flash chromatography. When some traces of imidazole wereobserved, EtOAc (20 mL) was added. After washing with water(2 10 mL), the organic layer was dried over MgSO4, filtered andevaporated under reduced pressure to afford the pure derivative of type IIIa.

According to the analysis of related databases, 853909-08-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ouach, Aziz; Pin, Frederic; Bertrand, Emilie; Vercouillie, Johnny; Gulhan, Zuhal; Mothes, Celine; Deloye, Jean-Bernard; Guilloteau, Denis; Suzenet, Franck; Chalon, Sylvie; Routier, Sylvain; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 153 – 164;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, 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, SDS of cas: 17570-98-8, blongs to pyridine-derivatives compound. SDS of cas: 17570-98-8

2-Bromo-1-(pyridin-2-yl)ethanone hydrobromide 8a(20.0 g, 71.1 mmol) and K2CO3 (14.8 g, 107 mmol) were suspended in acetone (100 mL), andthe suspension was stirred at room temperature for 1.5 hr. To a solution of ethyl cyanoacetate (60.4 g, 534 mmol) in acetone (100 mL) was addedK2CO3 powder (29.6 g, 214 mmol), and the mixture was stirred at 45C for 1 hr. To this mixture was added dropwise the suspension obtained earlier by small portions at 45C, and the resulting mixture was stirred at 45C for 3 h, filtered after cooled to room temperature, and then concentrated under reduced pressure. The residue was taken up withEtOAc, washed with H2O and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. To the obtained oil was added 4 mol/L HCl/EtOAc (250 mL) and the mixture was stirred at 60 C for 3 h, and concentrated under reduced pressure. A solution ofNaHCO3 was added to the residue and the mixture was extracted with EtOAc, washed with brine, dried over anhydrous MgSO4,and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/EtOAc = 4/1), then added dropwise 4 mol/L HCl/EtOAc (20 mL) after dissolved in EtOAc (20 mL), concentrated under reduced pressure, and crystalized from EtOAc to yieldcompound 10a (3.08 g, 15%) as a colorless solid: 1H-NMR (DMSO-d6)d 1.30 (3H, t, J=7.0 Hz), 4.25 (2H, q, J=7.0 Hz), 7.48-7.54 (2H, m), 8.13-8.19 (2H, m), 8.61-8.63 (1H, m), 13.47 (1H, br), 1H not detected.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, and friends who are interested can also refer to it.

Reference:
Article; Nishida, Haruyuki; Arikawa, Yasuyoshi; Hirase, Keizo; Imaeda, Toshihiro; Inatomi, Nobuhiro; Hori, Yasunobu; Matsukawa, Jun; Fujioka, Yasushi; Hamada, Teruki; Iida, Motoo; Nishitani, Mitsuyoshi; Imanishi, Akio; Fukui, Hideo; Itoh, Fumio; Kajino, Masahiro; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3298 – 3314;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem