Tag: M.W:200-300

Electric Literature of 175205-82-0, 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. 175205-82-0, name is 2-Bromo-3-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

Step 2: A mixture of 2-bromo-3-(trifluoromethyl)pyridine (50 mg), 2-[4- (ethylsulfonyl)phenyl]-N-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yI)phenyl]acetamide (104 mg), Cs2C03 (87 mg) and PdCl2(dppf)-CH2Cl2 adduct (10 mg) in acetonitrile (1.5 mL) and water (0.5 mL) was sealed in a vessel and heated in the microwave at 100C for 30 mins. The reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was purified by MDAP to afford 2-[4-(ethylsulfonyl)phenyl]-N-{4-[3-(trifluoromethyl)-2- pyridinyl]phenyl}acetamide (32 mg) as a white solid. ‘H-NMR (400 MHz, DMSO-rf6) delta ppm 1.10 (t, J= 7.2 Hz, 3H), 3.28 (q, J= 7.2 Hz, 2H), 3.85 (s, 2H), 7.42 (d, J= 8.4 Hz, 2H), 7.62 (m, 3H), 7.70 (d, J= 8.4 Hz, 2H), 7.86 (d, J= 8.4 Hz, 2H), 8.28 (dd, = 1.2 Hz, 8.0 Hz, 1H), 8.89 (d, J= 4.4 Hz, 1H), 10.46 (s, 1H); 19F-NMR (376 MHz, DMSO-t?) delta ppm -55.98; MS(ES+) m/z 449 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175205-82-0, 2-Bromo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WANG, Yonghui; CAI, Wei; LIU, Qian; MENG, Qinghua; CHENG, Yaobang; YANG, Ting; ZHANG, Guifeng; XIANG, Jianing; WU, Chengde; WO2013/29338; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 53937-02-3, Adding some certain compound to certain chemical reactions, such as: 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone,molecular formula is C12H11NO2, 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 53937-02-3.

a) 8-(4-Benzyloxy)-2-oxopyridin-1(2H)-yl)-6-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one 8-Bromo-6-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one (0.20 g, 0.68 mmol), 4-benzyloxy pyridinone (0.18 g, 0.89 mmol), and Cs2CO3 (0.24 g, 0.75 mmol) were suspended in DMSO (4.0 mL), and the air was removed under vacuum for 15 min. The system was flushed with Ar and the process repeated. 8-Hydroxyquinoline (30 mg, 0.21 mmol) and copper iodide (0.17 g, 0.89 mmol) were added to the suspension, and the evacuation/Ar flushing process was repeated twice more. The reaction mixture was heated at 130 C. for 18 h under N2. The mixture was cooled, diluted with 5:1 MeOH/NH4OH (10 mL), and the resulting solution was stirred at ambient temperature for 30 min. The reaction was further diluted with CH2Cl2 (75 mL). The solution was filtered through silica gel, and the filtrate was concentrated under reduced pressure. The residue was diluted with CH2Cl2 and washed with brine (3*25 mL). The organic solution was dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. Flash chromatography (12 g ISCO column, (1:1 hexanes/EtOAc)/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 5 column volumes, increased to 50:50 over 20 column volumes and held for 4 column volumes; increased to 0:100 over 10 column volumes) followed by flash chromatography (12 g ISCO column, (1:1 hexanes/EtOAc)/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 5 column volumes, increased to 70:30 over 20 column volumes and held for 4 column volumes; increased to 25:75 over 10 column volumes) followed by trituration in hot EtOH provided the title compound (19 mg, 7%) as an off-white powder: mp 178-181 C.; 1H NMR (500 MHz, DMSO-d6) delta 8.29 (d, J=8.5 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.53 (t, J=5.5 Hz, 1H), 7.49-7.35 (m, 6H), 7.00 (dd, J=8.5, 2.0 Hz, 1H), 6.10 (dd, J=7.5, 2.5 Hz, 1H), 5.97 (d, J=2.5 Hz, 1H), 5.15 (s, 2H), 3.68 (s, 3H), 3.21-3.10 (m, 2H), 3.12 (t, J=6.5 Hz, 2H), 2.08-2.07 (m, 2H); ESI MS m/z 414 [M+H]+; HPLC (Method A) 97.2% (AUC), tR=16.5 min.

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. 53937-02-3, 4-Benzyloxy-2-(1H)-pyridone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2011/3793; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 625-92-3, 3,5-Dibromopyridine, 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, HPLC of Formula: C5H3Br2N, blongs to pyridine-derivatives compound. HPLC of Formula: C5H3Br2N

[0187] Step 1. 3,5-Dibromoisonicotinaldehyde. Lithium diisopropylamide (507 mmol, 1.2 eq.) was added to 200 mL of dry THF at -78 C under N2. A solution of 3,5-dibromopyridine (100 g, 424 mmol) in 537 mL of dry THF was then added drop-wise over 30 mm. The reaction mixture was stirred at -78 C for 1 h. Ethyl formate (34.4 g, 465 mmol) was added drop-wise and stirred at -78 C for 30 mm, then the reaction mixture was poured into ice-cold saturated aqueous NaHCO3 solution. The mixture was extracted with 3 x 500 mL of EtOAc. The organic layer was concentrated to provide a brown solid, which was filtered through a pad of silica gel (eluted with dichloromethane) to give the title compound as a yellow powder (70 g, 63%).

The synthetic route of 625-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth, W.; BAUMEISTER, Timm, R.; GOSSELIN, Francis; ZAK, Mark; ZHENG, Xiaozhang; WO2013/130935; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 159981-19-8, 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.159981-19-8, name is 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde, molecular formula is C8H6F3NO2, molecular weight is 205.13, as common compound, the synthetic route is as follows.

Resin-bound tetra-alkylcyanoborohydride (9.03 g, 21.2 mmol) was added to a preformed mixture of 7-(benzylthio)-1,2,3,4-tetrahydroisoquinoline (4 g, 14.1 mmol), 6-(2,2,2-trifluoroethoxy)nicotinaldehyde (3.18 g, 15.5 mmol), and glacial acetic acid (3.23 ml, 56.4 mmol) in MeOH (35 ml). The reaction vessel was fitted with a reflux condensor and heated to 40 C. overnight. The reaction mixture was cooled to room temperature, filtered through a fritted funnel, then neutralized by the addition of saturated aqueous NaHCO3 solution. The layers were cut and the aqueous phase extracted with EtOAc¡Á3. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by medium pressure liquid chromatography ?MPLC? (KP-Sil 100 g SNAP column, BIOTAGE system) eluting with 1% MeOH/DCM over 3 CV followed by a gradient of 6-9% MeOH/DCM over 8 CV to give the desired compound. LC/MS (m/z): 445 (M+H)+

The chemical industry reduces the impact on the environment during synthesis 159981-19-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck Sharp & Dohme Corp.; Berger, Richard; Blizzard, Timothy A.; Campbell, Brian T.; Chen, Helen Y.; Debenham, John S.; Dewnani, Sunita V.; Dubois, Byron; Gude, Candido; Guo, Zack Zhiqiang; Harper, Bart; Hu, Zhiyong; Lin, Songnian; Liu, Ping; Wang, Ming; Ujjainwalla, Feroze; Xu, Jiayi; Xu, Libo; Zhang, Rui; (64 pag.)US2018/9796; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1232431-11-6 ,Some common heterocyclic compound, 1232431-11-6, molecular formula is C6H7BrN2O, 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.

5-Bromo-4-methoxy-pyridin-2-ylamine (9.50 g, 46.79 mmol), hexane-2, 5-dione (7.08 mL, 60.83 mmol) and p-toluenesulfonic acid (0.81 g, 4.68 mmol) in toluene (80 mL) are stirred over night at l20C using a Dean-Stark-apparatus. The reaction mixture is concentrated under reduced pressure, taken up in DCM and purified by silica gel chromatography (DCM). Yield: 7.60 g (58%) ESI-MS: m/z = 281 and 283 [M+H]+ (Br-isotopic pattern) Rt(HPLC): 1.13 min (method 1)

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. 1232431-11-6, 5-Bromo-4-methoxypyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela Kay; BOUYSSOU, Thierry; GOTTSCHLING, Dirk; HEINE, Niklas; NETHERTON, Matthew Russell; (119 pag.)WO2019/161010; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 941294-54-8, 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.941294-54-8, name is 5-Bromo-2-methoxynicotinonitrile, molecular formula is C7H5BrN2O, molecular weight is 213.03, as common compound, the synthetic route is as follows.

Example 2 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-amine 35 ml (23.47 mmol) of hydrazine is added at room temperature to 5 g (23.47 mmol) of 5-bromo-2-methoxynicotinonitrile. The reaction medium is carried at 100 C. for 3 hours. After returning to room temperature, the precipitate obtained is filtered, rinsed with water and then dried at 50 C. to yield 3.6 g (72%) of 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-amine in the form of a yellow solid. LCMS (EI, m/z): (M+1) 214.05 1H NMR: deltaH ppm (400 MHz, DMSO): 12.18 (1H, s, NH), 8.38 (1H, d, CHarom), 8.37 (1H, d, CHarom), 5.66 (2H, s, NH).

The chemical industry reduces the impact on the environment during synthesis 941294-54-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PIERRE FABRE MEDICAMENT; KALOUN, El Bachir; BEDJEGUELAL, Karim; RABOT, Remi; KRUCZYNSKI, Anna; SCHMITT, Philippe; PEREZ, Michel; RAHIER, Nicolas; US2013/85144; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 625-92-3, 3,5-Dibromopyridine, 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, Quality Control of 3,5-Dibromopyridine, blongs to pyridine-derivatives compound. Quality Control of 3,5-Dibromopyridine

3-(Benzyloxy)-5-bromopyridine [1099] (Zhu. G.-D. et al., Bioorg. Med. Chem. Lett. 2006, 16, 3150-3155) [1100] A 500 mL three-necked flask was charged with sodium hydride (60% dispersion in oil; 9.6 g, 240 mmol, 2.0 equiv.) and fitted out with stir bar, dropping funnel, N2 balloon, and septa. The sodium hydride was washed with hexane (2¡Á150 mL), then anhydrous DMF (110 mL) was added. With stifling and intermittent ice cooling, benzyl alcohol (25 mL, 240 mmol, 2.0 equiv.) was added dropwise within 105 min. The temperature was kept high enough to permit efficient stifling and prevent excessive frothing. After the addition was finished, the dropping funnel was rinsed with anhydrous DMF. Stirring was continued at room temperature for 20 min. The flask was briefly opened to add 3,5-dibromopyridine (28.4 g, 120 mmol) all at once. The atmosphere was again replaced with N2, and the reaction mixture was stirred at room temperature for 15 h. A thin layer chromatogram (small aliquot quenched into EtOAc/H2O; silica gel, EtOAc/hexane 15:85) taken shortly before the end of this period demonstrated the near-absence of starting material (Rf 0.6) and the formation of a product (Rf 0.25); benzyl alcohol was detected at Rf 0.15. The bulk of DMF was distilled in an oil pump vacuum at a bath temperature of 40 C. into a receiver cooled with acetone/dry ice. Initial foaming was due to the evaporation of residual hexane. The receiver was subsequently changed to maintain a high vacuum. The residue was taken up in diethyl ether (300 mL) and the resulting suspension poured into ice water (300 mL). The phases were separated, and the aqueous phase was twice extracted with ether (100 mL each). The combined organic phases were washed with brine (100 mL) and dried over MgSO4 (15 g). Evaporation furnished an orange-colored liquid together with a colorless solid. After transfer into a 200 mL flask, benzyl alcohol was distilled off in an oil pump vacuum into a -78 C. receiver. The product began to crystallize after partial cooling, whereon methanol (60 mL) was added. Crystallization was initially allowed to proceed at room temperature, then in the freezer overnight. [1101] The product was isolated by suction filtration, washed with two portions of freezer-chilled methanol (20 mL each), and dried (40 C./oil pump) to obtain 23.2 g (73%) of light-tan crystals (mp 67-68.5 C.). The mother liquor was concentrated to a few mL, diluted with methanol (15 mL), seeded, and placed in the freezer. Isolation as above gave 1.7 g of a solid which upon TLC examination revealed contamination with polar material. The second mother liquor still contained substantial amounts of benzyl alcohol, which was removed by evaporation into a 50 mL flask and bulb-to-bulb distillation at 80 C. in an oil pump vacuum until by visual appearance no further distillate was formed. The dark residue (2.7 g) together with the impure second crystal fraction was taken up in CH2Cl2 (3 mL) and chromatographed on silica gel (25¡Á3.8 cm, EtOAc/hexane 1:9) to yield, after evaporation and drying, another 2.4 g (8%) of the product 2. 1H NMR (CDCl3, 300 MHz) delta 8.33 (narrow m, 2H), 7.50-7.32 (m, 6H), 5.11 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,625-92-3, 3,5-Dibromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; The Board of Trustees of the University of Illinois; PsychoGenics, Inc.; Chandrasekhar, Jayaraman; Kozikowski, Alan P.; Liu, Jianhua; Tueckmantel, Werner; Walker, Joel R.; Yuen, Po-wai; US2013/184313; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 148493-37-2, 2,6-Dichloro-3-iodopyridine, 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: C5H2Cl2IN, blongs to pyridine-derivatives compound. COA of Formula: C5H2Cl2IN

General procedure: To asolution of 3-bromo-2,6-dichloropyridine (4.70 g, 20.7 mmol) in DMSO (103 ml)was added cesium fluoride (12.6 g, 82.9 mmol) at room temperature. The mixturewas stirred at 80 C under air for 8 h. The mixture was poured into water atroom temperature and extracted with Et2O. The organic layer wasseparated, washed with water and brine, dried over Na2SO4and concentrated in vacuo. (400 Torr, 40 C). The residue was purified bycolumn chromatography (silica gel, eluted with EtOAc in hexane) to give 3-bromo-2,6-difluoropyridine (3B) (2.58 g, 64%) as colorless oil. 1H NMR (CDCl3)delta: 6.79 1H,dd, J = 8.3, 3.0 Hz), 8.03 (1H, ddd, J = 8.4, 8.4 7.0 Hz). 19F NMR(CDCl3) delta: -69.3 Hz, -63.8 Hz. The compound 4B-8B were prepared in a manner similarto that described for 3B.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,148493-37-2, 2,6-Dichloro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Article; Katoh, Taisuke; Tomata, Yoshihide; Tsukamoto, Tetsuya; Nakada, Yoshihisa; Tetrahedron Letters; vol. 56; 44; (2015); p. 6043 – 6046;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 80537-07-1, Adding some certain compound to certain chemical reactions, such as: 80537-07-1, name is 2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid,molecular formula is C14H10N2O2, 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 80537-07-1.

EXAMPLE 56 STR64 Thionyl chloride (240 mg) was added dropwise to a stirred mixture of 2-phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid [compound (I)] (320 mg) and N,N-dimethylformamide (one drop) in chloroform (10 ml), and then stirred under reflux for 4 hours. After cooling the mixture, chloroform was evaporated in vacuo to give acid chloride of compound (I). Triethylamine (338 mg) was added to a suspension of the acid chloride of compound (I) in methylene chloride (10 ml) under ice-cooling, and to this suspension a solution of 2-ethylpiperidine in methylene chloride was added dropwise. The mixture was stirred under ice-cooling and stood at room temperature overnight. Saturated sodium chloride aqueous solution (20 ml) was added to the mixture and extracted with chloroform (20 ml). The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (8 g) with chloroform as an eluent. The fractions containing the objective compound were combined and evaporated in vacuo to give 1-(2-phenylpyrazolo[1,5-a]pyridin-3-ylcarbonyl)-2-ethylpiperidine (263 mg). mp: 182-183 C. IR (Nujol): 1630, 1600, 1520 cm-1 NMR (DMSO-d6, delta): 0.69 (3H, t, J=7.0 Hz), 1.12-1.93 (8H, m), 2.73-3.17 (1H, m), 3.69-4.45 (2H, m) 7.07 (1H, td, J=7.0 Hz and 2.0 Hz), 7.29-8.00 (7H, m), 8.86 (1H, dd, J=7.0 Hz and 1.0 Hz) Analysis Calcd. for C21 H23 N3 O: C 75 65, H 6.95, N 12.60. Found: C 75.75, H 7.01, N 12.66.

According to the analysis of related databases, 80537-07-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4994453; (1991); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 5349-17-7, 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 5349-17-7, name is 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide. This compound has unique chemical properties. The synthetic route is as follows.

[0246] 7V-{4-[2-(Dimethylamino)ethoxy]phenyl}-4-(4-pyridinyl)-l,3-thiazol- 2-amine (29). A mixture of bromoketone hydrobromide 1 (0.63 g, 2.25 mmol) and l-(4-(2-(dimethylamino)ethoxy)phenyl)thiourea (28) (0.54 g, 2.25 mmol) in EtOH (20 mL) was stirred at reflux temperature for 2 h. The mixture was cooled to 20 0C, diluted with water (50 mL), the pH adjusted to ca. 8 with aqueous NH3 and the mixture stirred at 0 0C for 1 h. The precipitate was filtered, washed with water (5 mL), and dried. The crude solid was purified by column chromatography, eluting with a gradient (0-20%) of MeOH/EtOAc, followed by 1% aqueous NH3/MeOH/EtOAc, to give amine 29 (447 mg, 58%) as a an oil: 1H NMR delta 10.13 (s, 1 H, NH), 8.60 (dd, J= 4.5, 1.6 Hz, 2 H, H-2′, H-6′), 7.83 (dd, J= 4.5, 1.6 Hz, 2 H, H-3′, H-5′), 7.59-7.64 (m, 3 H, H-5, H-2″, H-6″), 6.95 (ddd, J= 9.0, 3.5, 2.2 Hz, 2 H, H-3″, H-5″), 4.02 (br t, J= 5.9 Hz, 2 H, CH2O), 2.61 (br t, J= 5.9 Hz, 2 H, CH2N), 2.22 [s, 6 H, N(CH3)3]; 13C NMR delta 164.0, 153.4, 150.0 (2), 147.6, 141.0, 134.4, 119.8 (2), 118.7 (2), 114.8 (2), 106.6, 66.0, 57.6, 45.4 (2); MS m/z341.5 (MH+, 100%).

According to the analysis of related databases, 5349-17-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLAND UNISERVICES LIMITED; WO2009/114552; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem