Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 757978-18-0, 5-Bromo-3-iodo-1H-pyrrolo[2,3-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 C7H4BrIN2, blongs to pyridine-derivatives compound. Computed Properties of C7H4BrIN2

To a 500 ml 3-neck flask, 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (32 g, 99.1 mmol) and DMF (300 ml) were added. The solution was cooled to -40 C. under nitrogen and sodium hydride (2.8 g, 118.9 mmol) was added in 2 batches. The mixture was stirred at -40 C. for 1 hour. Then SEM-Cl (21 ml, 118.9 mmol) in DMF (50 ml) was added drop wise and the resulting mixture was allowed to stir at -40 C. for another 2 hours. The reaction was quenched with saturated NH4Cl (40 ml) and worked up with ethyl acetate, brine, dried with Na2SO4, concentrated to dryness. Silica chromatography of the crude using a gradient of ethyl acetate and hexane afforded 5-bromo-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (32.8 g, 73% yield). NMR (500 MHz, DMSO-d6) delta 0.06 (s, 9H), 0.91 (m, 2H), 3.62 (m, 2H), 5.70 (s, 2H), 8.04 (m, 1H), 8.11 (s, 1H), 8.51 (m, 1H). MS: m/z 455.9 (M+H+).

The synthetic route of 757978-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SGX Pharmaceuticals, Inc.; US2008/261921; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 60290-21-3, 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. 60290-21-3, name is 4-Chloro-1H-pyrrolo[3,2-c]pyridine, molecular formula is C7H5ClN2, 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.

4-Chloro-1H-pyrrolo[3,2-c]pyridine (247 mg) synthesized by the method disclosed in was dissolved in DMF (7.0 ml). After cooling to 0C, N-iodosuccinimide (382 mg) was added thereto. The resulting mixture was stirred at room temperature for 1 hour, and then chloroform and water were added thereto to separate the organic layer. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a darkbrown solid (455 mg). Physical properties: m/z[M+H]+ 279.1

According to the analysis of related databases, 60290-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; SAGARA, Takeshi; ITO, Satoru; OTSUKI, Sachie; SOOTOME, Hiroshi; EP2657233; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 141-86-6, 2,6-Diaminopyridine, 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, Application In Synthesis of 2,6-Diaminopyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2,6-Diaminopyridine

In a 100 mL three-necked round bottom flask, acetic anhydride (2.1 ml, 27.5 mmol) in 20 mL THF was added dropwise to a stirred mixture of pyridine-2,6-diamine (3.00 g, 27.5 mmol) and triethylamine (2.78 g, 27.5 mmol) in THF (40 ml) at 0C. After the reaction mixture was stirred at room temperature overnight, it was diluted with water (10 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with brine (2 x 1 OmL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with ethyl acetate/petroleum ether (10/i) to give the title compound as a solid. LCMS (ESI) calc?d for C7H9N30 [M+i ]: 152 found: 152; ?H NMR (300 MHz, CD3OD): oe7.38-7.32(m, 1H),718(d, J= 7.8 Hz, 1H), 6.24 (d,J= 8.1 Hz, 1H),2.08(s,3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,141-86-6, 2,6-Diaminopyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BENNETT, Frank; JIANG, Jinlong; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; SCOTT, Jack D.; TANG, Haiqun; ZHAO, Zhiqiang; HUANG, Yuhua; HUNTER, David; YANG, Dexi; ZHANG, Zhibo; FU, Jianmin; BAI, Yunfeng; ZHENG, Zhixiang; ZHANG, Xu; YOUNG, Katherine; XIAO, Li; (580 pag.)WO2016/206101; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 733757-89-6, tert-Butyl 3-(trifluoromethyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate, 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, 733757-89-6, blongs to pyridine-derivatives compound. Application In Synthesis of tert-Butyl 3-(trifluoromethyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate

Description 21 : 6-methyl-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4- c] pyridineUnder an inert atmosphere of argon, LiAIH4 (2.3 M in THF; 7.5ml; 17.3mmol) was added dropwise over 2 minutes to a cool (O0C) stirring solution of 6-tert-butoxycarbonyl-3- (trifluoromethyl)-4,5,6,7-tetrahydro-1 H-pyrazolo[3,4-c]pyridine (2.0Og; 8.45mmol) in anhydrous THF (42ml). The resulting mixture was stirred in an oil bath at 580C for 17 hours, cooled to O0C, and quenched by the careful addition of an aqueous solution of sodium potassium tartrate (1 M; 50ml). After stirring at room temperature for 1 hour, the mixture was diluted with diethyl ether (50ml) and more aqueous sodium potassium tartrate (1 M; 50ml). After stirring at this temperature for a further 1 hour, the mixture was partitioned between water (100ml) and diethyl ether (200ml). The separated aqueous phase was extracted with ethyl acetate (200ml), and the combined organic phase was dried (MgSO4) and concentrated in vacuo. The resulting off-white solid (1.39g) was purified using an SCX column giving the title compound as a yellow solid (1.23g; 6.01 mmol)LC/MS (ES): Found 206 (ES+), retention time 1.81 mins. C8H10F3N3 requires 205.1 H-NMR (400MHz, CDCI3): 2.48 (3H, app s), 2.74 (4H, app s), 3.58 (2H, app s), 5.01(1 H, br s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,733757-89-6, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/113795; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 757978-18-0, 5-Bromo-3-iodo-1H-pyrrolo[2,3-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, 757978-18-0, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine

100 mL round bottom flaskIodo-1H-pyrrole [2,3-b] pyridine (M1) (100.0 mg, 3.1 mmol)20 mL of dichloromethane, triethylamine (930 mg, 9.2 mmol), DMAP (40 mg, 0.31 mmol),Benzenesulfonyl chloride (N1) (1100 mg, 6.2 mmol) was dissolved in 10 mL of dichloromethane under ice-cooling,Dropping funnel through the constant pressure drop into the solution, the drop is completed, stirring at room temperature 1h,TLC detection, no M1 remaining, washed 3 times, liquid separation, the organic phase anhydrous sodium sulfate drying,The solvent was removed by concentration and recrystallized from ethyl acetate (5 mL) to give a white solid which was dried to give 5-bromo-3-iodo-1- (phenylsulfonyl) -1H-pyrrole [2,3-b] pyridine (B8).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,757978-18-0, its application will become more common.

Reference:
Patent; Fudan University; Zhou, Yaming; Yang, Chengbin; Hong, Hui; Liu, Xiaofeng; Yang, Yongtai; Ling, Yun; Gu, Yu; Deng, Mingli; (38 pag.)CN106117181; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 118650-08-1, 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. 118650-08-1, name is Methyl 2-(5-bromopyridin-3-yl)acetate, molecular formula is C8H8BrNO2, 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.

(5-Bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 30 mg, 0.149 mmol), palladium acetate (2.2 mg, 0.010 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (8.2 mg, 0.020 mmol), potassium phosphate (63 mg, 0.297 mmol) and water (0.2 mL) were added to a solution of (E)-1-(4-{1-[3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-3-ethyl-1-penten-3-ol (Example 38-(6); 50 mg, 0.099 mmol) in toluene (2 mL). After replacement with nitrogen, the mixture was stirred at 100C for 2.5 hours. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate = 1:1) to give the target compound as a colorless oil (12.5 mg, 24%). 1H-NMR (chloroform-d): 0.66 (6H, t, J=7.26Hz), 0.93 (6H, t, J=7.25Hz), 1.65 (4H, q, J=7.34Hz), 1.98 (6H, s), 2.11 (4H, q, J=7.42Hz), 2.35 (3H, s), 3.68 (2H, s), 3.72 (3H, s), 6.03 (1H, d, J=15.99Hz), 6.76 (1H, d, J=16.00Hz), 6.91 (2H, s), 6.97-7.01 (2H, m), 7.33 (1H, d, J=7.91Hz), 7.49 (1H, s), 8.35 (1H, d, J=2.14Hz), 8.47 (1H, d, J=2.14Hz).

According to the analysis of related databases, 118650-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1894911; (2008); 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.100-55-0, name is 3-Pyridinemethanol, molecular formula is C6H7NO, molecular weight is 109.13, as common compound, the synthetic route is as follows.Computed Properties of C6H7NO

General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, PdCl2(CH3CN)2 (0.05mol, 5mol%), Bi(OTf)3 (0.05mol, 5mol%), K2CO3 (1mmol) were added. Substrates 1 (1mmol) and MeOH (2mL) were added subsequently. The reaction tube was vacuumed and backfilled with oxygen (3 times). Then the reaction mixture was stirred at 60C for 3h in the presence of an oxygen balloon. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. Subsequently, the combined organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography with hexane/ethyl acetate to afford the corresponding products 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100-55-0, 3-Pyridinemethanol, and friends who are interested can also refer to it.

Reference:
Article; Hu, Yongke; Li, Bindong; Tetrahedron; vol. 73; 52; (2017); p. 7301 – 7307;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 123148-66-3 ,Some common heterocyclic compound, 123148-66-3, molecular formula is C7H9NO2, 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 2: 3-(2, 6-d ifluoro-3 , 5-dimethoxyphenyl)-1-[(2-methoxypyridin-4-yl)methylJ-8-(morpholin-4-ylmethyl)- 7-(phenylsufonyl)-1, 3,4, 7-tetrahydro-2H-pyrrolo[3 ?,2 ?:5, 6Jpyrido[4, 3-dJpyrimidin-2-one To a solution of 3 -(2,6-difluoro-3 ,5 -dimethoxyphenyl)-8-(morpholin-4-ylmethyl)-7- (phenylsulfonyl)- 1,3 ,4,7-tetrahydro-2H-pyrrolo[3 ?,2? : 5,6]pyrido[4,3 -d]pyrimidin-2-one(10.0 mg, 0.0 167 mmol, from Step 1), (2-methoxypyridin-4-yl)methanol (23.2 mg,0.167 mmol, purchased from Ark Pharma, catalog number: AK-2 8607) in tetrahydrofuran (1.0 mL, 12 mmol) were added triphenylphosphine (26.0 mg, 0.099 1 mmol) and diethyl azodicarboxylate (16 iL, 0.10 mmol). The resulting mixture was stirred at 60 C for 12 h. The reaction was diluted with MeOH (4.0 mL) and purified by RP-HPLC (pH 10) toafford the product. LC-MS calculated for C35H35F2N607S [M+H] mlz: 721.2; found 721.0.

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. 123148-66-3, (2-Methoxypyridin-4-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INCYTE CORPORATION; WU, Liangxing; ZHANG, Colin; HE, Chunhong; SUN, Yaping; LU, Liang; QIAN, Ding-Quan; XU, Meizhong; ZHUO, Jincong; YAO, Wenqing; WO2014/7951; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6332-56-5, Adding some certain compound to certain chemical reactions, such as: 6332-56-5, name is 3-Nitropyridin-2(1H)-one,molecular formula is C5H4N2O3, 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 6332-56-5.

2-Oxo-3-nitro-N-(carbomethoxymethyl)-pyridinone (109). 2-Hydroxy-3-nitropyridine 108 (10 g, 71.38 mmole) is mixed with pulverized potassium carbonate (10.9 g, 78.5 mmole) and 30 mL of DMF. After 10 min, methyl bromoacetate (10.4 mL, 107 mmole) is added. The resulting mixture is stirred at room temperature for 4.5 hr. The reaction is quenched by water and extracted by ethyl acetate. The organic layer is then washed with brine, dried over MgSO4, filtered and evaporated to give an oil which is chromatographed over flash silica with EtOAc to give 109.

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. 6332-56-5, 3-Nitropyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Procter & Gamble Company; US5672598; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 139022-25-6, 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. 139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid, molecular formula is C8H6N2O2, 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 solution of imidazo[1 ,2-a]pyridine-6-carboxylic acid (0.100 g, 0.62 mmol), 5-(3-chlorobenzyl)pyridin-2-amine (0.161 g, 0.74 mmol), 1 -[b/s(dimethylamino)methylene]- 7/-/-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (0.353 g, 0.93 mmol) and A/-A/,A/-diisopropylethylamine (0.240 g, 1 .86 mmol) in A/,A/-dimethylformamide (3 ml_) was stirred at room temperature for 2 h. The crude sample was dissolved in minimal A/,A/-dimethylformamide and purified via prep-HPLC (Boston C18 21 *250 mm 10 pm column; acetonitrile/0.01 % aqueous trifluoroacetic acid) to give A/-(5-(3-chlorobenzyl)pyridin-2-yl)imidazo[1 ,2-a]pyridine-6-carboxamide (0.048 g, 0.1 12 mmol, 18.0%) as a faint yellow solid. 1 H NMR (500 MHz, Dimethylsulfoxide-c/6) d 1 1 .26 (s, 1 H), 9.57 (s, 1 H), 8.41 (d, J = 1 .8 Hz, 1 H), 8.37 (d, J = 2.5 Hz, 1 H), 8.34 (dd, J = 4.8, 4.8Hz, 1 H), 8.22 (d, J = 2.0 Hz, 1 H), 8.12 (d, J = 8.5 Hz, 1 H), 8.02 (d, J = 9.4 Hz, 1 H), 7.77 (dd, J = 8.5, 2.3 Hz, 1 H), 7.36- 7.33 (m, 2H), 7.29-7.25 (m, 2H), 4.00 (s, 2H); LCMS (ESI) m/z: 363.0 [M+H]+.

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 139022-25-6, Imidazo[1,2-a]pyridine-6-carboxylic acid.

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