Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 1187830-47-2, 4,5,6,7-Tetrahydro-2H-pyrazolo[4,3-b]pyridine hydrochloride, 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, Formula: C6H10ClN3, blongs to pyridine-derivatives compound. Formula: C6H10ClN3

To a mixture of 4,5,6,7-tetrahydro-2H-pyrazolo[4,3-b]pyridine (500 mg, 3.13 mmol, HCl, CAS1187830-47-2) and (Boc)2O (752 mg, 3.45 mmol) in MeOH (15 mL) was added aq.K2CO3 (3 M, 2.09 mL). The reaction mixture was stirred at 20 C. for 15 hours. On completion, the mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (SiO2) to give the title compound (500 mg, 71% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 12.05 (s, 1H), 7.55 (s, 1H), 3.66-3.55 (m, 2H), 2.65 (t, J=6.4 Hz, 2H), 1.94-1.82 (m, 2H), 1.51 (s, 9H).

The synthetic route of 1187830-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 851484-95-2, Adding some certain compound to certain chemical reactions, such as: 851484-95-2, name is 2-Chloro-5-fluoronicotinaldehyde,molecular formula is C6H3ClFNO, 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 851484-95-2.

Example 37: Synthesis of 3-Fluoro-l,7,llb-triaza-benzo[c]fluorene-6-carboxylic acid ethyl es [0321] To a solution of compound SMI (0.8 g, 5 mmol) and compound SM2 (1.02 g, 5 mmol) in ethanol (50 mL) was added piperidine (1.28 g, 15 mmol) and the mixture was stirred at room temperature for 20 min. The reaction mixture was heated to reflux for 16h. After cooling, the mixture was filtered and washed with ethanol, dried to get compound 7A as yellow solid (0.82 g, 79 yield). LCMS: m/z 309.9 (M+H)+.

According to the analysis of related databases, 851484-95-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HADDACH, Mustapha; WO2015/172123; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 717843-56-6, 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. 717843-56-6, name is 3-Bromo-2-methoxy-5-methylpyridine. A new synthetic method of this compound is introduced below.

Example 172 (7bR,11aS)-N-(2-Methoxy-5-methyl-3-pyridinyl)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-6-amine A solution of tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate from Example 56, Part B (968 mg, 2.81 mmol), 3-bromo-2-methoxy-5-methylpyridine (515 mg, 2.55 mmol), and NaOt-Bu (404 mg, 4.20 mmol) in anhydrous toluene (40 mL) was stirred under an argon atmosphere in a sealable test tube. The mixture was degassed with argon at 85 C. for 30 min then cooled to 50 C. Tris(dibenzylideneacetone)dipalladium(0) (62 mg, 67 mumol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (84.0 mg, 135 mumol) were added; the reaction was sealed and heated at 85 C. for 16 h. The reaction was cooled to room temperature, diluted with EtOAc, filtered through a bilayer pad of diatomaceous earth and silica gel, and concentrated. Purification of the residue by flash column chromatography (silica gel, 10-50% EtOAc/hexanes) provided tert-butyl (7bR,11aS)-6-(2-methoxy-5-methyl-3-pyridinyl)-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate (1.16 g, 89%). A solution of the intermediate in CH2Cl2 (20 mL) at -10 C. was treated with TFA (6 mL) and stirred for 1 h. Upon concentration in vacuo, the residue was partitioned between a 1:1 solution of CH2Cl2/satd NaHCO3 (100 mL). The aqueous phase was extracted with CH2Cl2 (4*75 mL). The combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography [silica gel, 5-50% (80:18:2 CHCl3/MeOH/concd NH4OH)/CH2Cl2] and trituration with CH2Cl2/Et2O/hexanes provided the title compound of Example 172 (590 mg, 65%) as a tan solid: mp 122-124 C.; 1H NMR (300 MHz, CDCl3) delta 7.40 (s, 1H), 6.99 (s, 1H), 6.88 (s, 1H), 6.77 (s, 1H), 5.84 (br s, 1H), 4.75 (d, J=14.1 Hz, 1H), 4.58 (d, J=14.1 Hz, 1H), 4.34-4.16 (m, 1H), 4.01 (s, 3H), 3.89-3.69 (m, 1H), 3.58-3.39 (m, 1H), 3.38-3.13 (m, 2H), 3.11-2.99 (m, 1H), 2.98-2.85 (m, 2H), 2.81-2.68 (m, 1H), 2.61-2.42 (m, 1H), 2.19 (s, 3H), 2.01-1.77 (m, 3H); ESI MS m/z 367 [C21H26N4O2+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,717843-56-6, 3-Bromo-2-methoxy-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Robichaud, Albert J.; Fevig, John M.; Mitchell, Ian S.; Lee, Taekyu; Chen, Wenting; Cacciola, Joseph; US2004/186094; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 185315-53-1, Adding some certain compound to certain chemical reactions, such as: 185315-53-1, name is 3-Chloro-2-(chloromethyl)pyridine,molecular formula is C6H5Cl2N, 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 185315-53-1.

General procedure: A mixture of N-tert-butyl-7-(3,3-difluoropyrrolidin-l-yl)-3H-triazolo[4,5-d]pyrimidin-5- amine (25 mg, 0.08 mmol), NEt3 (14.6 mg, 0.144 mmol) and l-(bromomethyl)-2- (trifluoromethyl)benzene (26.8 mg, 0.112 mmol) in 2 mL DMF was stirred at room temperature for 5 h. The mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt . After evaporation of the product containing fractions 5.2 mg (14 %) of the title compound was isolated. MS(m/e): 456.4 (MH+). Example 27; N-[(3S)-l-[5-(tert-Butylamino)-3-[(3-chloropyridin-2-yl)methyl]triazolo[4,5- d]pyrimidin-7 -yl] pyrrolidin- 3 -yl] acetamide; In analogy to the procedure described for the synthesis of N-tert-butyl-7-(3,3- difluoropyrrolidin- l-yl)-3-[[2- (trifluoromethyl)phenyl] methyl] triazolo [4, 5 -d] pyrimidin- 5 – amine (example 22) the title compound was prepared from N-[(3S)-l-[5-(tert-butylamino)- 3H-triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-yl]acetamide and 3-chloro-2- (chloromethyl)pyridine. MS(m/e): 444.4 (MH+).

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. 185315-53-1, 3-Chloro-2-(chloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ROEVER, Stephan; ROGERS-EVANS, Mark; NETTEKOVEN, Matthias; SCHMITT, Sebastien; GRETHER, Uwe; KIMBARA, Atsushi; WO2015/32769; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine, the common compound, a new synthetic route is introduced below. COA of Formula: C5H2BrClN2O2

A mixture of 2- bromo-5-chloro-3-nitropyridine (1.00 g, 4.21 mmol), methyl 2,2-difluoro-2- (fluorosulfonyl)acetate (0.971 g, 5.05 mmol), and copper(I) iodide (0.963 g, 5.05 mmol) in DMF (10 mL) was heated at 85 oC for 16 h. Upon cooling to rt, the mixture was diluted with ethyl acetate (20 mL) and filtered through Celite. The filtrate was concentrated under vacuum to almost dryness. The residue was diluted with ethyl acetate (180 mL), washed with water (3 x 40 mL) and brine (30 mL), and dried over anhydrous MgSO4. The desired product, 5-chloro-3-nitro-2-(trifluoromethyl)pyridine (0.578 g, 2.55 mmol, 60.6% yield), was isolated as a light yellow oil by flash chromatography (80 g silica gel, solid loading, 5-20% ethyl acetate/hexane).1H NMR (500 MHz, CHLOROFORM-d) delta 8.89 (d, J=2.2 Hz, 1H), 8.25 (d, J=1.7 Hz, 1H).

The synthetic route of 75806-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; JALAGAM, Prasada Rao; NAIR, Satheesh Kesavan; PANDA, Manoranjan; FENG, Jianxin; WANG, Wei; LIU, Chunjian; ELLSWORTH, Bruce A.; SARABU, Ramakanth; SWIDORSKI, Jacob; HARTZ, Richard, A.; XU, Li; YOON, David S.; BENO, Brett R.; REGUEIRO-REN, Alicia; (457 pag.)WO2019/67702; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 103058-87-3 , The common heterocyclic compound, 103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde, 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.

n-Butyllithium (120 ml, 1.6M in hexane) is added to a suspension of 80.74 g of (3-methoxy- propyl)triphenylphosphonium bromide [11 1088-69-8] in 250 ml of tetrahydrofuran under an argon atmosphere at 0C. The reaction mixture is stirred at 0C for 50 minutes and then 28 g of 5-bromo-2-methoxypyridine-3-carbaldehyde [103058-87-3] are added. The reaction mixture is stirred at 0C for 1 hour and then at room temperature for 1 hour and diluted with tert-butyl methyl ether. The solution is washed with 1 M sodium bicarbonate solution. The organic phase is dried over sodium sulphate and evaporated. The title compound is obtained as a yellowish oil from the residue by flash chromatography (SiO2 60F). Rt = 5.03 (Gradient I)

The synthetic route of 103058-87-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2007/31558; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1443-42-1, 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. 1443-42-1, name is (4-Methylpyridin-3-yl)methanamine, molecular formula is C7H10N2, 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.

General procedure: To a solution of compound 3w (0.70g, 2.1mmol) in THF (10ml) was added phenyltrimethylammonium tribromide (0.79g, 2.1mmol). The reaction mixture was stirred at room temperature for 12h. Water (50mL) was added and the mixture was extracted with ethyl acetate (10mL×3), the combined organic phase was washed with water (30mL×2), dried over anhydrous Na2SO4 and concentrated to afford the intermediate 4w. To a solution of different pyridin-3-ylmethanamine derivatives (2.1mmol) in acetone (10ml) was added Et3N (0.43g, 4.2mmol). The reaction mixture was stirred for 5min and was added CS2 (0.24g, 3.15mmol) to continuously stir for 30min. The intermediate 4w were added respectively and this mixture was stirred at room temperature for 4h. Water (50mL) was added and the mixture was extracted with ethyl acetate (10mL×3), the combined organic phase was washed with brine (30mL×2), dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to provide the product.

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 1443-42-1, (4-Methylpyridin-3-yl)methanamine.

Reference:
Article; Li, Ridong; Ning, Xianling; Zhou, Shuo; Lin, Zhiqiang; Wu, Xingyu; Chen, Hong; Bai, Xinyu; Wang, Xin; Ge, Zemei; Li, Runtao; Yin, Yuxin; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 48 – 65;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 60010-03-9, Adding some certain compound to certain chemical reactions, such as: 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine,molecular formula is C6H4Cl2N2O2, 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 60010-03-9.

6-Chloro-4-methyl-3-nitro-2-pyrrolidin-1 -yl-pyridine (Intermediate compound)To a solution of crude 2,6-dichloro-4-methyl-3-nitro-pyridine (see previous reaction; 23.87g; 115mmol), pyrrolidine (11 ml 1.1 eq) in 100 ml_ acetonitrile was added TEA (ca. 50 ml 3eq). After stirring overnight at room temperature one aliquot of water was added to the reaction mixture and the acetonitrile was removed in vacuo. The remaining aqueous layer was extracted with EtOAc (3x15OmL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to yield a dark semi-solid. The crude material was purified by flash column chromatography (5-40% EtOAc in heptane) to yield 1 Og (26% over three steps) of the title compound as a yellow solid.

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. 60010-03-9, 2,6-Dichloro-4-methyl-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROSEARCH A/S; BROWN, William, Dalby; JESSEN, Carsten; MATTSSON, Cecilia; SOTT, Richard; STRØBAeK, Dorte; WO2010/122064; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 107351-82-6 , The common heterocyclic compound, 107351-82-6, name is 2-Bromo-5-phenylpyridine, molecular formula is C11H8BrN, 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.

EXAMPLE 5 Synthesis of 2,4-bis(4-tert-butylphenyl)-6-[4-(5-phenylpyridin-2-yl)phenyl]-1,3,5-triazine Under a stream of argon, 3.5 ml of a pentane solution containing 5.2 mmol of tert-butyl lithium was slowly added to 15 ml of tetrahydrofuran cooled to -78C, and 10 ml of tetrahydrofuran in which 0.61 g of 2-bromo-5-phenylpyridine had been dissolved was further added dropwise to this solution. After stirring at -78C for 30 minutes, 1.64 g of dichloro(tetramethylethylenediamine)zinc(II) was added thereto and stirred at -78C for 10 minutes and then at room temperature for 2 hours. A 35 ml portion of tetrahydrofuran prepared by dissolving 1.00 g of 2-(4-bromophenyl)-4,6-bis(4-tert-butylphenyl)-1,3,5-triazine synthesised by the method of Reference Example 1 and 0.12 g of tetrakis(triphenylphosphine)palladium(0) therein was added to this solution and stirred under heating reflux for 10 hours. The reaction solution was concentrated under a reduced pressure and the thus obtained solid was recrystallized from dichloromethane-methanol. The thus obtained crude product was purified by a silica gel column chromatography (eluding solution hexane:dichloromethane = 3:2 to 4:3) and then again recrystallized from dichloromethane-methanol to obtain a white solid of the intended 2,4-bis(4-tert-butylphenyl)-6-[4-(5-phenylpyridin-2-yl)phenyl]-1,3,5-triazine (1.05 g, yield 91%). Its melting point is shown in Table 4. In this case, a distinct point of glass transition was not observed. 1H-NMR (CDCl3): delta 1.45 (s, 18H), 7.44-7.60 (m, 3H), 7.65 (d, J=8.6 Hz, 4H), 7.88 (d, J=8,5 Hz, 2H), 7.88-7.94 (m, 1H), 8.07-8.15 (m, 3H), 8.74 (d, J=8.6 Hz, 4H), 8.93 (d, J=8.5 Hz, 2H), 9.09 (d, J=1.7 Hz, 1H). 13C-NMR (CDCl3): delta 31.2, 35.1, 120.3, 125.6, 126.9, 127.0, 128.8, 129.1, 129.6, 133.6, 134.1, 135.1, 136.2, 138.8, 141.2, 148.1, 156.1, 156.6, 170.9, 171.5.

The synthetic route of 107351-82-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH CENTER; EP1930329; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 886365-47-5, 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 886365-47-5, name is 1-(5-Bromo-2-chloropyridin-3-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1-(5-bromo-2-chloropyridin-3- yl)ethanone (4.85 g, 0.85 mmol) and N,N-dimethylformamide dimethyl acetal (15 mL, 113 mmol) was stirred at 85C for 90 minutes in an oil bath. The mixture was cooled to room temperature, and concentrated under reduce pressure. The residue was diluted by addition of ethanol (30 mL) and water (15 mL), acetic acid (3.3 mL, 58 mmol) and 2-hydrazinoethanol (1.83 mL, 26.9 mmol) was added thereto at room temperature, and the mixture was stirred at 90C for 4 hours in an oil bath. The mixture was cooled to room temperature, and neutralized by addition of a 1.0 mol/L aqueous solution of sodium hydroxide, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified in an automatic chromatography apparatus (n-hexane/ethyl acetate = 100/0- 0/100) to obtain 2-[5-(5-bromo-2-chloropyridin-3-yl)- 1H-pyrazol-1-yl]ethanol (3.62 g) as a mixture containing positional isomers. To a solution of 2-[5-(5-bromo-2- chloropyridin-3-yl)-1H-pyrazol-1-yl]ethanol (3.62 g) as a mixture containing positional isomers obtained in the above step in N,N-dimethylformamide (240 mL) was added potassium carbonate (3.31 g, 23.9 mmol) at room temperature, and the mixture was stirred at 120C for 2 hours in an oil bath. The reaction mixture was cooled, and an insoluble material was filtered off. The residue was washed with ethyl acetate, and the filtrate and the washes were combined. The solvent was distilled off under reduced pressure, and the residue was purified in an automatic chromatography apparatus (Yamazen Co. Ltd., High-flashTM column Amino, n-hexane/ethyl acetate = 100/0- 30/70) to obtain the title compound (101 mg, yield for 2 steps: 57%)?H NNR spectrum (CDC13, 400MHz) oe: 8.27 (1H, d, J =2.3 Hz), 8.18 (1H, d, J= 2.3 Hz), 7.55 (1H, d, J=2.0 Hz), 6.69 (1H, d, J = 2.0 Hz), 4.74-4.72 (2H, m),4.62-4.60 (2H, m)

According to the analysis of related databases, 886365-47-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; MIYAZAKI, Shojiro; INUI, Masaharu; KUROSAKI, Yasunobu; YAMAMOTO, Yuko; IZUMI, Masanori; SOMA, Kaori; PINKERTON, Anthony; KISHIDA, Masamichi; (309 pag.)WO2018/119444; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem