Category: pyridine-derivatives

Application of 912369-42-7, Adding some certain compound to certain chemical reactions, such as: 912369-42-7, name is Methyl 3-((tert-butoxycarbonyl)amino)picolinate,molecular formula is C12H16N2O4, 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 912369-42-7.

ter f-butyl f2-(hvdroxymethyl)py ridin-3-yll carbamate; To methyl 3-[(tert- butoxycarbonyl)amino]pyridine-2-carboxylate and methyl 2-[(tert- butoxycarbonyl)amino]nicotinate (5.00 g, 19.8 mmol) is added THF/MeOH (30 mL/3 mL) and the reaction is cooled to 0 C whereupon sodiumborohydride (1.49 g, 39.6 mmol) is added. The reaction is warmed to rt and stirred for four hours. The reaction mixture is then EPO dissolved in EtOAc and washed with saturated sodium bicarbonate solution. The organic layers are combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford the title compound and tert-buty [3-(hydroxymethyl)pyridin-2- yljcarbamate which are separated by preparatory HPLC (5-95% MeCN/water/0.1% TFA). The desired isomer is confirmed by ID NOE NMR experiments. 1H NMR delta 8.78 (br s, IH), 8.17 (m, IH), 8.10 (d, IH), 7.27 (dd, IH), 4.64 (s, 2H), 1.46 (s, 9H). LCMS (ES, M+H=225).

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. 912369-42-7, Methyl 3-((tert-butoxycarbonyl)amino)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/106326; (2006); 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 72093-03-9, name is 3-Chloro-2-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 72093-03-9

Preparation of teit-butyl 4-((3-chloropyridin-2-yl)methyl)-4- hydroxypiperidine-l-carboxylate. A solution of 3-chloro-2-methylpyridine (64.2 mg, 0.50 mmol) in THF (1 mL) was sparged with N2 and cooled to -78 C before n-butyllithium (2.5 M THF, 0.16 mL, 0.41 mmol) was added dropwise. After stirred at -78 C for 45 min, the mixture was warmed to RT and stirred for 2 h before cooled again to -78 C. A solution of tert-butyl 4-oxopiperidine-l-carboxylate (74.2 mg, 0.37 mmol) in THF (1.5 mL) was added dropwise. After stirring for 2 hr at -78 C, the mixture was warmed to rt and stirred for 2 d. The reaction was then partitioned between EtOAc and sat. H4CI (aq). After phase-separation, the aqueous was extracted with EtOAc (3x). The organic extracts were combined, dried over Na2S04, filtered and concentrated. The residue was purified by silica chromatography (10-90% EtOAc in hexanes) to afford the title compound as a colorless oil (103.5 mg, 85%). MS (apci) m/z = 227.1 (M+H-Boc).

With the rapid development of chemical substances, we look forward to future research findings about 72093-03-9.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COLLIER, James; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; RAMANN, Ginelle A.; TANG, Tony P.; REN, Li; WALLS, Shane M.; (946 pag.)WO2018/71454; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 156072-84-3, 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 156072-84-3 as follows.

[0307] Cesium carbonate (0.734 g, 2.25 mmol) and 5-chloro-3-methylpyridine-2-carbonitrile (0.206 g, 1.35 mmol) wereadded at room temperature to a suspension of the optically active form of cis-1-(diphenylmethyl)-5-hydroxy-3-(piperidin-4-yl)-4-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one (0.212 g, 0.451 mmol) produced in ReferenceExample 27 in DMSO (2 mL), and the mixture was stirred at 150C for 2 hours. The reaction suspension wascooled to room temperature, then diluted with ethyl acetate, and washed with brine. The obtained organic layer wasdried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residuewas purified by silica gel column chromatography [elute: hexane/ethyl acetate = 92/8 – 50/50 (gradient)] to obtain thetitle compound (0.226 g, yield: 86%, optically active form).[0308] 1H-NMR (400MHz, CDCl3) delta: 8.14 (1H, d, J=3Hz), 7.40-7.36 (6H, m), 7.12-7.06 (5H, m), 6.91 (1H, d, J=3Hz),6.69 (1H, s), 4.53 (1H, d, J=7Hz), 3.94-3.86 (3H, m), 3.69 (1H, d, J=3Hz), 3.08-3.00 (2H, m), 2.89-2.81 (1H, m), 2.45(3H, s), 2.02-1.80 (4H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156072-84-3, its application will become more common.

Reference:
Patent; Daiichi Sankyo Company, Limited; KOBAYASHI, Hideki; ARAI, Masami; KANEKO, Toshio; TERASAKA, Naoki; (95 pag.)EP3081566; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 50501-38-7, Adding some certain compound to certain chemical reactions, such as: 50501-38-7, name is 6-(Hydroxymethyl)picolinonitrile,molecular formula is C7H6N2O, 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 50501-38-7.

P4: For alternative syntheses, see [36?38]. The reaction was performed under nitrogen. SeO2 (386 mg, 3.48 mmol) and P3 (933 mg, 6.96 mmol) were stirred in dioxane (30 mL; neither dried nor degassed) at 110°C (bath temperature) for 24 h to give a dark yellow solution and black precipitate of selenium. The mixture was filtered through Celite to remove selenium. Celite was washed with CH2Cl2. Purification by chromatography (10 g of silica; CH2Cl2)gave pale yellow eluate of the product. White solid: 692 mg(5.24 mmol; 75percent; C7H4N2O; MW 132.12).

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. 50501-38-7, 6-(Hydroxymethyl)picolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shavaleev, Nail M.; Eliseeva, Svetlana V.; Inorganica Chimica Acta; vol. 427; (2015); p. 81 – 86;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 847729-27-5, 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.847729-27-5, name is Methyl 2-chloro-5-fluoronicotinate, molecular formula is C7H5ClFNO2, molecular weight is 189.57, as common compound, the synthetic route is as follows.

STEP 2. Methyl 5-fluoro-2- (4-fluorobenzvl) nicotinate; To a stirred solution of methyl 2-chloro-5-fluoronicotinate (step 1, 350 mg, 1.85 mmol) and dichlorobis [triphenylphosphine] nickel (1I) (362 mg, 0.55 mmol) in tetrahydrofuran (15 mL) was added a 0.5 M solution of 4-fluorobenzylzinc chloride in tetrahydrofuran (5.54 mL, 2.77 mmol) at 0 C under nitrogen. The resulting mixture was warmed to room temperature and stirred for 16 h. The mixture was poured into saturated aqueous ammonium chloride solution (50 mL) and extracted with ethyl acetate (100 ML). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (10/1) to afford 439 mg (90%) of the title compounds as colorless oil: H-NMR (CDC13) 6 8.56 (1H, d, J = 2.8 Hz), 7.91 (1H, dd, J = 8.6, 2.9 Hz), 7.26-7. 19 (2H, m), 6.98-6. 92 (2H, M), 4.52 (2H, s), 3.89 (3H, s); MS (ESI) m/z 264 (M + H) +.

Statistics shows that 847729-27-5 is playing an increasingly important role. we look forward to future research findings about Methyl 2-chloro-5-fluoronicotinate.

Reference:
Patent; PFIZER INC.; PFIZER JAPAN, INC.; WO2005/21508; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1111637-94-5, Adding some certain compound to certain chemical reactions, such as: 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine,molecular formula is C8H7BrN2, 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 1111637-94-5.

Step 7: 3-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine To a solution of 5-bromo-3-methyl-lH-pyrrolo[2,3-b]pyridine (20 g, 94.8 mmol) in N,N- dimethylformamide (200 mL) was added potassium acetate (27.9 g, 284.4 mmol) and 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (28.8 g, 113.74 mmol). The resulting mixture was degassed with nitrogen for 5 min, l,l’-Bis(diphenylphosphino)ferrocene- palladium(II)dichloride (6.65g, 9.48mmol) was added and the mixture was degassed with nitrogen once more for 5 min. The reaction mixture was stirred overnight at 80-90 C. The reaction mixture was poured into water, extracted with (3 x 200 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 9% to 50% ethyl acetate in petroleum ether) affording 3-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine as a white solid (10.5 g, 43%): lU NMR (400MHz, DMSO-d6), delta 11.360 (s, 1H), 8.371-8.375 (d, = 1.6 Hz, 1H), 8.097-8.100 (s, = 1.2 Hz, 2H), 7.17 (s, 1H), 3.296 (s, 3 H), 1.245 (s, 12H).

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. 1111637-94-5, 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); 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 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5-(Trifluoromethyl)pyridin-3-amine

5-(Trifluoromethyl)pyridin-3 -amine (977 mg, 6.03 mmol, Anichem, P20551 , North Brunswick, NJ) was treated with THF (40 mL) and LiHMDS (1.0 M in THF, 13.26 mL, 13.26 mmol) slowly dropwise at RT and stirred at this temperature for 20 min. The solution was then cooled in an ice bath and di-tert-butyl dicarbonate (1.38 g, 6.33 mmol) was added and the solution stirred warming to RT overnight. LC-MS indicated partial conversion to bis(Boc) material (M+l =363.2). The reaction mixture was treated with additional di-tert-butyl dicarbonate (1.38 g, 6.33 mmol) and of 1M LiHMDS and stirred overnight (16 h). The reaction mixture was concentrated and the crude material was treated with 0.2M HC1 (aq., 30 mL) and extracted with EtOAc (100 mL). The organic layer was washed with a saturated solution of NaHCC>3 (aq.) and brine and dried over MgS04, filtered and concentrated. The resulting crude product was purified by silica gel chromatography (20-50% EtOAc in hexanes) to afford bis(teri-butyl (5- (trifluoromethyl)pyridin-3-yl)carbamate) (729 mg, 33 % yield) as a yellow crystalline solid. MS (ESI, pos. ion) m/z: 363.0 (M+l). .H NMR (400 MHz, CDCl3) delta ppm 8.80 (1 H, s), 8.58 – 8.64 (1 H, m), 7.75 (1 H, s), 1.44 (18 H, s). 19F NMR (377 MHz, CDCl3) delta ppm -62.36 (3 F, s).

With the rapid development of chemical substances, we look forward to future research findings about 112110-07-3.

Reference:
Patent; AMGEN INC.; D’AMICO, Derin C.; HERBERICH, Bradley J.; JACKSON, Claire L.M.; PETTUS, Liping H.; TASKER, Andrew; WANG, Hui-Ling; WU, Bin; WURZ, Ryan; WO2012/148775; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1132-37-2, 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. 1132-37-2, name is Dipyridin-2-ylmethane, molecular formula is C11H10N2, 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.

100cc Schlenk tube and then in the oxygen and three times replacement with argon and vacuum for removal of water Pt[2,2′-bpyridine]Cl2 (90.34mg, 0.214mmol) was added and dissolved with EtOH solvent (20ml). To this solution was added dipyridin-2-ylmethane (40mg, 0.235mmol) was dissolved in EtOH (15ml). The mixture is contained in a Schlenk tube for 5 hours and then put Reflux NH4PF6 (114.9mg, 0.705mmol) was refluxed with 80C for 36 hours under argon gas. After confirming the completion of the reaction by TLC whether the mixture was cooled at room temperature. Conducted a filter to remove the resulting precipitate was cooled, and the supernatant was filtered through a filter and then dried in vacuum and then washed CHCl3 to give the title compound (yield: 57%).

According to the analysis of related databases, 1132-37-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sunchon National University Industry-Academic Cooperation Foundation; Jung, Min Chul; Kim, Song Chan; (13 pag.)KR101602456; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 936011-17-5 ,Some common heterocyclic compound, 936011-17-5, 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.

To the solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (compound 74a, 25.00 g, 115.70 mmol) in THF (250 mL) was added MeMgBr (3M in 2-Me-THF, 50.20 mL, 150.40 mmol) drop wise at -78 C over 30 mins. After being stirred at -78 C for 0.5 h, the mixture was warmed to rt slowly and then quenched with 100 mL saturated NFLCl, diluted with 400 mL water and extracted with 150 mL EA twice. The combined organic layer was washed with 180 mL water and 100 mL brine, dried over Na2S04 and concentrated to give the cmde product compound 74b (27.00 g) as a yellow oil. MS calc?d 232 (MFL), measured 232 (MFL).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,936011-17-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DEY, Fabian; KOU, Buyu; LIU, Haixia; SHEN, Hong; WANG, Xiaoqing; ZHANG, Weixing; ZHANG, Zhisen; ZHANG, Zhiwei; ZHU, Wei; (203 pag.)WO2019/238616; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3430-22-6, 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 3430-22-6, name is 3-Bromo-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3.98 g of the acid obtained in the previous step (20 mmol, 1 eq.) in 50 ml of methanol is reflux heated in the presence of 4 ml of concentrated sulfuric acid. The mixture is allowed to return to ambient temperature and extracted 3 times with ethyl acetate. The organic phase is dried on Na2SO4 and the solvent is evaporated. 2.65 g (62%) of esterified product is obtained. NMR (1H, CDCl3): 4.02 (s; 3H), 7.64 (d, J=4.9 Hz; 1H), 8.63 (d, J=4.9 Hz; 1H), 8.88 (s; 1H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 3430-22-6, 3-Bromo-4-methylpyridine.

Reference:
Patent; Imbert, Thierry; Monse, Barbara; Koek, Wouter; US2005/80085; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem