Day: March 24, 2022

Synthetic Route of 19235-89-3, 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. 19235-89-3, name is 4-Chloropyridine-2-carbonitrile. A new synthetic method of this compound is introduced below.

A three-neck, 3L round bottomed flask fitted with a mechanical stirrer and a reflux condersor was charged with 4-aminophenol (41.35 g, 0.38 mol) and N5N- dimethylacetamide (500 mL). The resulting solution was degassed with bubbling nitrogen before potassium tert-butoxide was added portionwise (44.54 g, 0.40 mol). The solution became green at first, then became an off-white suspension, to which was added 4- chloropyridine-2-carbonitrile (50.00 g, 0.36 mol) in N,N-dimethylacetamide (300 mL) in one portion. The mixture turned brown within minutes and it was heated to 900C overnight. In the next morning, the mixture was cooled to rt and the solvent was removed under vacuum. The resulting residue was partitioned between water (1.5 L) and EtOAc (1.5 L). K2CO3 was added to adjust the pH to slightly basic and the layers were separated. The aqueous layer was extracted with EtOAc (IL). The combined organic phase was dried over MgSO4, filtered and concentrated. The resulting residue was dissolved in dichloromethane and absorbed onto a plug of silica gel (~ 1 kg). It was then eluted with 25% to 75% EtOAc in hexanes to afford 4-(4-aminophenoxy)pyridine-2-carbonitrile (18.9 g, 25%): 1H NMR (DMSO-^5) delta ppm 8.48 (d, IH), 7.51 (d, IH), 7.04 (dd, IH), 6.83 (dd, 2H), 6.60 (dd, 2H), 5.18 (s, 2H); MS ES 212 (M+H), RT 0.97 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,19235-89-3, 4-Chloropyridine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/110763; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 934180-48-0, 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.934180-48-0, name is 4-Chloro-2-methoxy-3-nitropyridine, molecular formula is C6H5ClN2O3, molecular weight is 188.57, as common compound, the synthetic route is as follows.

Tin(ll)chloride dihydrate (12 g, 53.19 mmol) was added to a solution of 4-chloro-2- methoxy-3-nitropyridine (2 g, 10.64 mmol) in ethyl acetate (30 ml.) and the resultant suspension heated at 70 C with stirring for 2 h. The reaction mixture was cooled to ambient temperature, the pH adjusted to pH 9-10 by addition of saturated sodium carbonate (aq.) and extracted with ethyl acetate (3 x 10OmL). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the crude product. Purification by chromatography on silica gel with EtOAc:heptane (1 :9, v/v) as eluent afforded the product as a colourless oil (1.28 g, 76 %).Data for 3-amino-4-chloro-2-methoxypyridine: MS (ESI) m/z: 159/161 ([M+H]+).

The chemical industry reduces the impact on the environment during synthesis 934180-48-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; N.V. ORGANON; WO2007/39563; (2007); 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 945954-94-9, name is Methyl 6-bromo-3-methoxypicolinate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 945954-94-9

A solution of methyl 6-bromo-3-methoxypicolinate (3.0 g, 12.19 mmol) andLiOHH2O (1.4 g, 33.36 mmol) in 1,4-dioxane / H20 (15 mL / 15 mL) was stirred at RT overnight. The mixture was filtered and the filtrate was adjusted to pH = 3 by aqueous HC1 (2 M) and extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2504 andconcentrated to give the crude product of 6-bromo-3-methoxypicolinic acid (2.1 g, yield: 73 %)without further purification. ?H-NMR (CDC13, 400 MHz) 10.05 (br s, 1H), 7.70 (d, J = 8.8 Hz,1H), 7.40 (d, J = 8.8 Hz, 1H), 4.01 (s, 3H). MS (M+H): 232 / 234.

With the rapid development of chemical substances, we look forward to future research findings about 945954-94-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/205593; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 62002-31-7, 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 62002-31-7 as follows.

To a stirred solution of 4,5-dibromo-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one (3 g, 8.88 mmol, 1 equiv.) and 1H,4H,5H,6H,7H-imidazo [4,5-c]pyridine (1.1 g, 8.88 mmol, 1.00 equiv.) in 1,4- dioxane (30 mL) was added DIEA (2.3 g, 17.75 mmol, 2 equiv.) dropwise at 0 degree Celsius under nitrogen atmosphere. The mixture was stirred at 100 degrees Celsius overnight. Desired product could be detected by LCMS. The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with CH2Cl2 / MeOH (10:1 to 5:1) to afford 4-bromo-5-[1H,4H,5H,6H,7H-imidazo[4,5-c]pyridin-5-yl]-2- (oxan-2-yl)-2,3-dihydropyridazin-3-one (3g, 88.89%) as white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62002-31-7, its application will become more common.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 52605-96-6, 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.52605-96-6, name is 2-Chloro-3-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.57, as common compound, the synthetic route is as follows.

The boronic acid was prepared as described in Intermediate 4 to give 2.8mmole. (quant. crude). The boronic acid (2. 14MMOL) was dissolved in acetonitrile (2. 4ML) and 3-methoxy-2-chloropyridine (368mg; 2. 6mmol) was added. After mixing, tetrakis palladium was added (25mg; 0. OLMOL%), follwed by 0. 8ml of water and K2CO3 (887mg; 6. 5MOL). The reaction mixture was heated at 160C in A Personal Chemistry EMRYS Microwave for 300S. After reaction completion, the solvents were evaporated and the residue was dissolved in EtOAc and washed with water and brine. The organic layer was dried over MGSO4, filtered and evaporated. The residue was then dissolved in A 1 : 1 mixture of THF/42NKOH and heated until saponification was complete. The basic layer was then extracted with EtOAc and acidified with cone. HCI. The aqueous layer was then extracted three times with EtOAc. The combined organic layers were dried over MGS04, filtered and evaporated to give the desired material as A yellow solid (425MG ; 76%). MS :MH+= 264

Statistics shows that 52605-96-6 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-3-methoxypyridine.

Reference:
Patent; RENOVIS, INC.; WO2005/32493; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 23628-31-1 ,Some common heterocyclic compound, 23628-31-1, molecular formula is C6H6N2O2, 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.

Step 1) Preparation of ethyl 6-aminopicolinate: To a solution of 2-amino-6-pyridinecarboxylic acid (6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 0 C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate (5.5 g, 76%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23628-31-1, its application will become more common.

Reference:
Patent; GlaxoSmithKline LLC; VU, Chi, B.; DISCH, Jeremy, S.; SPRINGER, Stephanie, K.; BLUM, Charles, A.; PERNI, Robert, B.; (212 pag.)EP2273992; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 96630-88-5, 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. 96630-88-5, name is 4-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, 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 66 Preparation of (4bR,8aR,9R)-N-(3-(2-(2-methoxyethoxy)ethoxy)pyridin-4-yl)-ll- methyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthren-3-amine (66), hydrochloride salt Step 1. Synthesis of 4-chloro-3-(2-(2-methoxyethoxy)ethoxy)pyridine, A mixture of 4-chloropyridin-3-ol (100 mg, 0.772 mmol), l-bromo-2-(2- methoxyethoxy)ethane (141 mg, 0.772 mmol) and CS2CO3 (503 mg, 1.544 mmol) in dimethylacetamide (5 mL) was irradiated in a microwave at 120 C for two hours. The reaction mixture was cooled to room temperature and poured into 20 mL of water. The aqueous solution was extracted with ethyl acetate 3×20 mL. The organic layer was combined, was washed with brine (50 mL), was dried over anhydrous sodium sulfate, was filtered and was concentrated. The crude product was purified via flash column chromatography on silica gel to afford 4-chloro-3-(2-(2-methoxyethoxy)ethoxy pyridine (87.4 mg, 48.9%). MS (EI) for C10H14CINO3: 232.0 (MH+).

According to the analysis of related databases, 96630-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEKTAR THERAPEUTICS; ANAND, Neel; AURRECOECHEA, Natalia; CHENG, Lin; DENG, Bo-liang; O’MAHONY, Donogh; MU, Yongqi; KROGH-JESPERSEN, Erik; (215 pag.)WO2016/182840; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1196152-34-7, 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 1196152-34-7, name is 2-Bromo-6-methoxypyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

(S)-2-Hydroxy-2,4-dimethylpentanoic acid (3073 g; 21 mol; 1.00 eq.), 4-dimethylaminopyridine (128 g; 1 mol; 0.05 eq.) and dichloromethane (24.5 L) are placed in a 100 L reactor. The reaction mixture is cooled to about 0 C. Pyridine (3.75 L) and dichloromethane (6 L) are added while maintaining the temperature at 0-5 C. (0238) Trimethylchlorosilane (5.8 L; 46 mol; 2.20 eq.) is added while maintaining the temperature below 5 C. The reaction mixture is warmed to 20 C. and stirred for 4 hours 30 minutes at this temperature, and then cooled to 0 C. N,N-Dimethylformamide (55 ml; 0.71 mol; 0.03 eq.) is added while maintaining the temperature below 5 C., and oxalyl chloride (1622 ml; 18.9 mol; 0.90 eq.) is then added while maintaining the temperature below 5 C. The reaction mixture is stirred for 1 hour at this temperature and N,N-dimethylformamide (27.50 ml; 0.36 mol; 0.02 eq.) is then added. The reaction mixture is warmed to about 20 C. and stirred for 1 hour at this temperature. (0239) A solution of 2-bromo-4-amino-6-methoxypyridine (3543 g; 17.4 mol; 0.83 eq.) in a dichloromethane (27.3 L)/pyridine (1.9 L) mixture is added to the preceding solution while maintaining the temperature below 25 C. The reaction mixture is stirred for 30 minutes at this temperature. The reaction progress is monitored by TLC with 5% control. (0240) A solution of acetic acid (23 L; 41 mol; 1.95 eq.) in ethanol (19 L) is prepared in a new disposable container of suitable volume and then poured into the reaction mixture while maintaining the temperature below 25 C. The reaction medium is stirred overnight at about 20 C. The reaction progress is monitored by TLC. (0241) An aqueous solution of hydrochloric acid (2.4 L; 12.00 M; 28.77 mol; 0.78 V) in water (27 L) is prepared in a new disposable container of suitable volume and then poured into the reaction medium and stirred for 10 minutes. The aqueous phase is discarded and the organic phase is then washed with water (30 L). The aqueous phase is discarded and the organic phase is then washed again with a solution prepared from NaOH (1 177.29 g; 29.43 mol; 1.40 eq.) in water (30 L). The aqueous phase is discarded and the organic phase is then washed again with water (30 L). (0242) The aqueous phase is discarded. The organic phase is clarified on a filter packed with active charcoal (921 g) and the cake is then washed with dichloromethane (10 L). The filtrate is then placed in the reactor and concentrated at reflux, distillate (37 L). Cyclohexane (43 L) is added to the reactor, which is then refluxed until the head temperature reaches 75 C. (distilled volume 22.5 L). Cyclohexane (10 L) is added and the reactor is allowed to cool to 27 C. An (S)-N-(2-bromo-6-methoxypyrid-4-yl)-2-hydroxy-2,4-dimethylpentanamide initiator (138 g; 0.42 mol; 0.02 eq.) is added to promote the crystallization. The reaction mixture is cooled to 20 C. and then filtered through a 25 mum filter gauze. (0243) The reactor and the filter are rinsed with cyclohexane (10 L). The solid is dried in an oven at 45 C. under vacuum to give (S)-N-(2-bromo-6-methoxypyrid-4-yl)-2-hydroxy-2,4-dimethylpentanamide (3.7 kg; 65%). (0244) 1H NMR (400 MHz, DMSO-d6): 10.0 (bs, 1H); 7.73 (s, 1H); 7.33 (s, 1H); 5.70 (bs, 1H); 3.80 (s, 3H); 1.79-1.67 (m, 2H); 1.49 (dd, J=13.6 & 5.2 Hz, 1H); 1.32 (s, 3H); 0.89 (d, J=6.4 Hz, 3H); 0.78 (d, J=6.4 Hz, 3H)

According to the analysis of related databases, 1196152-34-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Galderma Research & Development; BOITEAU, Jean-Guy; DAVER, Sebastien; RODEVILLE, Nicolas; (19 pag.)US2019/10124; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.23056-46-4, name is 2-Bromo-5-methyl-3-nitropyridine, molecular formula is C6H5BrN2O2, molecular weight is 217.02, as common compound, the synthetic route is as follows.Product Details of 23056-46-4

[00259] A round bottom flask was charged with 2-bromo-5-methyl-3- nitropyridine (60.53 g, 278.9 mmol) and CuCN (27.52 g, 307.3 mmol) The flask was evacuated, and back-filled with nitrogen. DMF (150 mL) was added via cannula. The solution was heated to 70 0C for 1.5 hours. After cooling to room temperature, the reaction mixture was poured into EtOAc (500 mL) and water (250 mL). Both phases were filtered through a 1 cm bed of celite. The layers were separated, and the organic phase washed with water (2 * 100 mL) then with a solution of 1 :1 sat. aq. NH4CI / NH4OH (2 x 100 mL). The combined aqueous layers were extracted with EtOAc (2 * 200 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound (36.1Og, 79% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23056-46-4, 2-Bromo-5-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2009/9740; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 40473-07-2 ,Some common heterocyclic compound, 40473-07-2, molecular formula is C6H6BrNO, 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-bromo-6-methoxypyridine (10 g, 0.053 mol) in dry ACN (100 ml_), was added A/-bromosuccinimide (18.82 g, 0.106 mol) at RT. The reaction mixture was stirred at 90? for 16 h. The completion of reaction was monitored by TLC. After completion, the reaction was filtered through a celite bed, diluted with water (30 mL) and exacted with 10% EtOAc in petroleum ether (2 x 100 mL). The combined organic layer washed with water (10 mL), brine (10mL) dried over Na2SC>4 and concentrated. The resulting crude material was purified by crystallization (5 mL DCM in 50 mL n- pentane). The solid was filtered, washed with n-pentane and then dried unber vacuum to get afford the tittle compound. Yield: 35% (4.92 g, off white solid). 1H NMR (400 MHz, CDCI3): d 7.70 (d, J = 8.4 Hz, 1 H), 6.62 (d, J = 8.4 Hz, 1 H), 3.93 (s, 3H), LCMS: (Method A) 367.9 (M+H), Rt. 2.4 min, 96.7% (Max).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,40473-07-2, its application will become more common.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; WISHART, Grant; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; RAKESH, Paul; (250 pag.)WO2020/39028; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem