Month: August 2021

Reference of 65156-94-7 ,Some common heterocyclic compound, 65156-94-7, molecular formula is C7H5ClN2, 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.

B. 1-Benzenesulfonyl-5-chloro-1H-pyrrolo[3,2-b]pyridine The title compound is prepared from 5-chloro-1H-pyrrolo[3,2-b]pyridine as described in EXAMPLE 41, Part A. The crude product is purified by column chromatography eluding with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes to give the title compound as a solid. 1H NMR (CDCl3, 300 MHz) delta8.23 (d, 1H), 7.87 (d, 2H), 7.81 (d, 1H), 7.62 (m, 1H), 7.49 (m, 2H), 7.26 (d, 1H) 6.81 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,65156-94-7, its application will become more common.

Reference:
Patent; Aventis Pharma Deutschland GmbH; US6281227; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 17997-47-6, 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. 17997-47-6, name is 2-(Tributylstannyl)pyridine, molecular formula is C17H31NSn, 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.

A mixture of 2-tri-n-butylstannylpyridine (18.4 g, 0.05 mol), 1,5-dibromo-2,4-dimethyl-benzene (5.3 g, 0.02 mol), bis(triphenylphosphine) palladium(II) chloride (0.28 g, 0.4 mmol) and lithium chloride (6.4 g, 0.15 mol) in dry toluene (50 mL) was heated at 116 C under N2 for 24 h. After the reaction mixture cooled to room temperature, saturated KF solution (50 mL) was added and the solution stirred for 30 min. The precipitated solid was removed by filtration and washed with water (50 mL). NaHCO3 solution (10%, 150 mL) was then added to the combined filtrates, extracted with dichloromethane (3×200 mL), and dried over MgSO4. Removal of solvent under reduced pressure and purification of the residue by column chromatography (silica, hexane/dichloromethane=8:1; V/V) gave the desired product as a pale yellow solid (3.62 g, 69%).

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 17997-47-6, 2-(Tributylstannyl)pyridine.

Reference:
Article; Tan, Shuai; Wu, Xiugang; Zheng, Yanqiong; Wang, Yafei; Chinese Chemical Letters; vol. 30; 11; (2019); p. 1951 – 1954;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 130722-95-1, Adding some certain compound to certain chemical reactions, such as: 130722-95-1, name is 3-(Benzyloxy)-5-bromopyridine,molecular formula is C12H10BrNO, 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 130722-95-1.

3-Benzyloxy-5-bromopyridine (4.73 g, 18.0 mmol) was dissolved in tetrahydrofuran (25 rnL) and cooled to 0 0C.Isopropylmagnesiumchloride (10 mL, 2.0 M in THF) was syringed in and the reaction mixture was stirred for 2 hrs at room temperature. N.N-dimethylformamide (3 mL) in tetrahydrofuran (10 mL) was added and stirring was continued for an additional hour. The solution was quenched with 2 N HCl to pH of 3 then partitioned between ethyl acetate and water. The organic layer was separated and concentrated to give a residue which was purified using flash chromatography to give 3-benzyloxy-5-formylpyridine (2.00 g, 53%) as white solid. 1H NMR (DMSO-^6): delta 10.1 (s, IH), 8.72 (d, IH), 8.66 (d, IH), 7.84 (m, IH), 7.42-7.48 (m, 5H), 5.28 (s, 2H).

According to the analysis of related databases, 130722-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2007/84560; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55279-29-3, 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. 55279-29-3, name is 3-Aminoisonicotinaldehyde, molecular formula is C6H6N2O, 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.

3-Amino-pyridine-4-carbaldehyde (5.00 g, 40.9 mmol) was dissolved in DCM (60 mL), ethyl 4-piperidinecarboxylate (7.57 mL, 49.1 mmol) and NaBH(OAc)3 (10.4 g, 49.1 mmol) were added and the reaction mixture was heated in a microwave reactor at 60 C. for 5 min. The reaction mixture was diluted with DCM (100 mL) and quenched with sat aq Na2CO3 (50 mL). The organic fraction was washed with sat aq NH4Cl (30 mL). The combined aq fractions were extracted with DCM (2*50 mL) and the combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the crude title compound as a yellow gum (11.3 g). LCMS (ES+): 264.1 [MH]+.

According to the analysis of related databases, 55279-29-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROXIMAGEN LIMITED; Evans, David; Carley, Allison; Stewart, Alison; Higginbottom, Michael; Savory, Edward; Simpson, Iain; Nilsson, Marianne; Haraldsson, Martin; Nordling, Erik; Koolmeister, Tobias; US2014/357623; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 636-73-7, Adding some certain compound to certain chemical reactions, such as: 636-73-7, name is Pyridine-3-sulfonic acid,molecular formula is C5H5NO3S, 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 636-73-7.

PREPARATION 1 Pyridine-3-sulfonyl chloride hydrochloride A mixture of pyridine-3-sulfonic acid (15.0 g), phosphorous pentachloride (24.0 g) and phosphorous oxychloride (30 mL) was heated to 120 C. for 16 h. The reaction was cooled to room temperature, and the resulting suspension was saturated with HCl (g). A white precipitate was collected, washed with CHCl3, and dried in vacuo to afford the title compound (15.6 g). 1 H NMR (400 MHz, DMSO) delta 8.98 (s, 1H), 8.85 (d, 1H), 8.66 (d, 1H), 8.02 (t, 1H).

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. 636-73-7, Pyridine-3-sulfonic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; US6124314; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 50488-42-1, 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. 50488-42-1, name is 2-Bromo-5-(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 301A 5-(trifluoromethyl)-2-pyridinecarbonitrile Copper (I) cyanide (14.1 g) and 2-bromo-5-trifluoromethylpyridine (3.00 g, 13.3 mmol) in dry DMSO (70 mL) were combined and heated at 180 C. for 2 hours, cooled, and poured into NH4OH (3M). The mixture was then extracted with ethyl acetate (3*500 mL), washed with water (1*200 mL), dried (MgSO4), filtered and the filtrate concentrated under reduced pressure to provide the title compound. 1H NMR (DMSO, 300 MHz) delta 8.22 (m, 1H), 8.42 (m, 1H), 9.01 (s, 1H).

According to the analysis of related databases, 50488-42-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbott Laboratories; US6933311; (2005); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 872619-43-7, 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.872619-43-7, name is Methyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylate, molecular formula is C9H7BrN2O2, molecular weight is 255.07, as common compound, the synthetic route is as follows.

Example 7; Methyl 5-[4-(2-morpholin-4-ylethoxy)phenyl]-l^-pyrrolo[2,3-6]pyridine-3-carboxylate; Triisopropyl borate (0.39 mL, 1.7 mmol) was added to a stirred solution of 4-[2-(4-bromophenoxy)ethyl]morpholine (0.163 g, 0.57 mmol; described in: Lednicer, D., et al, J.Med. Chem. 1965, 8, 52-57) in anhydrous tetrahydrofuran (4 mL). The resulting solution wascooled to -70 C and H-butyllithium (1.1 mL, 1.6 M in hexane, 1.76 mmol) was addeddropwise. The mixture was stirred at -70 C for 1 h and was then allowed to warm to roomtemperature. Hydrochloric acid (aq. 2.85 mL, 1 M, 2.85 mmol) was added and the mixturewas stirred for 2 min, followed by addition of sodium carbonate (0.604 g, 5.7 mmol). Afterstirring for another 2 min, methyl 5-bromo-l//-pyrrolo[2,3-6]pyridine-3-carboxylate (0.100 g,0.4 mmol) and [l,r-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethaneadduct (0.047 g, 0.057 mmol) were added and the resulting mixture was heated at 65 C overnight. The solvent was evaporated and the residue was purified on a silica gel column usingdichloromethane/methanol, (95:5), as the eluent. Re-crystallization from acetonitrile gave0.048 g (31% yield) of the title compound as crystals:’H NMR (CDC13, 400 MHz) 8 10.06 (m, 1 H), 8.57 (m, 2 H), 8.06 (s, 1 H), 7.58 (m, 2 H),7.02 (m, 2 H), 4.29 (m, 2 H), 3.94 (s, 3 H), 3.85 (m, 4 H), 2.99 (m, 2 H), 2.77 (m, 4 H).

Statistics shows that 872619-43-7 is playing an increasingly important role. we look forward to future research findings about Methyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylate.

Reference:
Patent; ASTRAZENECA AB; WO2006/1754; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6000-50-6, 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 6000-50-6 as follows.

A solution of 100mg of Intermediate 11(0.35 minol, 1.00 eq) in DMF (10 mL) was treated with108 mg of N,N?-disuccinimidyl carbonate (0.42 minol, 1.20 eq) and 51.4 mg of 4-dimethylaminopyridine (0.42 minol, 1.20 eq) and was left over night at room temperature. Asuspension of 81 .2 mg of 2,3-dihydro-1 H-pyrrolo[3,4-c]pyridine dihydrochloride (0.42 minol, 1 .20eq) and 667 pL of triethylamine (4.78 minol, 3.60 eq) in DMF (5 mL) was added. The reactionmixture was left for 3 days at room temperature. The mixture was poured into water. The aqueous phase was three times extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2504 and the solved was removed under reduced pressure. The residue was purified by preparative reverse phase HPLC to yield the desired productExample 11(30 mg, 20percent).1H-NMR (400MHz, DMSO-d6): oe [ppm] = 1.09 (d, 3H), 2.40-2.47 (m, IH), 2.79-2.87 (m, IH),3.42-3.54 (m, IH), 4.26-4.38 (m, IH), 4.37-4.37 (m, IH), 4.80-4.83 (m, 4H), 7.41 -7.47 (m, I H), 7.65 – 7.72 (m, 2H), 7.72 – 7.79 (m, 2H), 8.50 (d, I H), 8.61 (s, I H), 8.66 (s, I H).U PLC-MS (Method 2): R= 0.81 min; MS (ESipos): mz [M÷H] 432.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6000-50-6, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; GIESE, Anja; QUANZ-SCHOEFFEL, Maria; MUeLLER, Thomas; GUeNTHER, Judith; BOeHNKE, Niels; GRIEBENOW, Nils; BARAK, Naomi; BOeMER, Ulf; NEUHAUS, Roland; OSMERS, Maren; KOPITZ, Charlotte Christine; KAULFUSS, Stefan; REHWINKEL, Hartmut; WEISKE, Joerg; BADER, Benjamin; CHRISTIAN, Sven; HILLIG, Roman; (426 pag.)WO2018/86703; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 175201-94-2, 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. 175201-94-2, name is 4-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

Example 6 (1,3-Dimethyl-4-morpholin-4-ylpyrazolo[5,4-b]pyridin-5-yl)-N-({[4-fluoro 3-(trifluoromethyl)phenyl]amino}carbonyl)carboxamide (65) A solution of 4-chloro-1,3-dimethylpyrazolo[5,4-b]pyridine-5-carboxylic acid (450 mg) and morpholine (870 mg) in DMF (15 mL) was stirred at room temperature for 5 h, and then concentrated under reduced pressure. The residue was treated with water (10 mL), and the resulting solid was filtered, washed with water, and dried under high vacuum. The solid was suspended in anhydrous dichloromethane (20 mL) and treated with oxalyl chloride (1.0 mL) and anhydrous DMF (0.1 mL). The mixture was stirred at room temperature for 1 h, filtered, and the filtrate was concentrated under reduced pressure. The residue was cooled in an ice-bath and slowly treated with a saturated solution of ammonia in THF (20 mL). The suspension was removed from the ice-bath, stirred at room temperature for 1 h, and filtered. The solid was washed with water and dried under high vacuum to give 1,3-dimethyl-4-morpholin-4-ylpyrazolo[5,4-b]pyridine-5-carboxamide as a white powder. A portion of this material (0.33 g) was dissolved in hot toluene (30 mL) and azeotroped for 1 h.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175201-94-2, 4-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Laborde, Edgardo; Robinson, Louise; Meng, Fanying; Peterson, Brian T.; Villar, Hugo O.; Anuskiewicz, Steven E.; Ishiwata, Yoshiro; Yokochi, Shoji; Matsumoto, Yukiharu; Kakigami, Takuji; Inagaki, Hideaki; Jomori, Takahito; Matsushima, Kouji; US2003/96705; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 271-73-8, 1H-Pyrazolo[3,4-b]pyridine, 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, Computed Properties of C6H5N3, blongs to pyridine-derivatives compound. Computed Properties of C6H5N3

To a solution of 1 H-pyrazolo[3,4-b]pyridine (I-6) (4 g, 34 mmol) in DMF (150 mL) was added KOH (7.6 g, 136 mmol) at 0 C. The mixture was stirred at room temperature for 30 min. To the resulting mixture was added iodine (15 g, 61 mmol) in portions at 0C and the mixture was stirred at room temperature overnight. TLC (petroleum ether/ EtOAc = 1 :1) showed the reaction was complete. The reaction mixture was poured into ice water and extracted with CH2CI2 (300 mL x 2). The combined organic layers were washed with sat. aq.Na2S03 (300 mL chi 2), brine (200 mL x 3), dried over Na2S04 and concentrated in vacuo to give 3-iodo-1 H-pyrazolo[3,4-b]pyridine (I-7) (7 g, 84%) as a yellow solid.

The synthetic route of 271-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem