Day: April 18, 2022

Reference of 79491-46-6, 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 79491-46-6, name is 2,6-Dibromo-3-methoxy-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Alternate Procedures Useful for the Synthesis of Compound 39 Preparation of 5,7-dibromo-4-methoxy-7-azaindole 36: Vinylmagnesium bromide (0.85 M in THF, 97.7 mL, 83.0 mmol) was added over 30 min. to a stirring solution of 2,6-dibromo-3-methoxy-5-nitropyridine (7.4 g, 23.7 mmol) in THF (160 mL) at -75 C. The solution was stirred 1 h at -75 C., overnight at -20 C., recooled to -75 C. and quenched with saturated aqueous NH4Cl (~100 mL). The reaction mixture was allowed to warm to rt, washed with brine (~100 mL) and extracted with Et2O (150 mL) and CH2Cl2 (2*100 mL). The combined organics were dried (MgSO4), filtered and concentrated. The residue was purified by flash column chromatography (SiO2, 3:1 hexanes/EtOAc) to yield 5,7-dibromo-4-methoxy-7-azaindole 36 (1.10 g, 3.60 mmol, 15%) as a pale yellow solid.

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 79491-46-6, 2,6-Dibromo-3-methoxy-5-nitropyridine.

Reference:
Patent; Wang, Tao; Wallace, Owen B.; Zhang, Zhongxing; Meanwell, Nicholas A.; Bender, John A.; US2002/119982; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 851484-95-2, 2-Chloro-5-fluoronicotinaldehyde, 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 C6H3ClFNO, blongs to pyridine-derivatives compound. Computed Properties of C6H3ClFNO

To a suspension of methyltriphenylphosphonium bromide (0.68 g, 1.92 mmol) in anhydrous THF (20 ml), n-BuLi (1.06 ml of a 1.6 M solution in Cy, 1.69 mmol) was added under nitrogen at -78 C. The cold bath was then removed and the reaction was allowed to reach room temperature and stirred for 1 h. To the resulting suspension at 0 C., a solution of 2-chloro-5-fluoro-3-pyridinecarbaldehyde (0.18 g, 1.13 mmol) dissolved in THF (10 ml) was slowly added. Stirring was maintained at room temperature for 4 h. The reaction was quenched with water (8 ml), the two phases were separated and the aqueous layer back-extracted with DCM. The organic phase was dried (Na2SO4) and the solvent was removed under reduced pressure. Purification by flash chromatography on silica gel (Cy/EtOAc 95/5) gave the title compound D41 (0.05 g, 0.27 mmol, 24% yield).UPLC: rt=0.70 min, peaks observed: 158 (M+1, 100%) and 160 (M+1, 33%). C7H5ClFN requires 157. 1H NMR (400 MHz, CDCl3) delta (ppm): 8.20 (d, 1H), 7.62 (dd, 1H), 7.01 (ddd, 1H), 5.83 (d, 1H), 5.59 (d, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,851484-95-2, 2-Chloro-5-fluoronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; ALVARO, GIUSEPPE; AMANTINI, DAVID; BELVEDERE, SANDRO; US2009/22670; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 92276-38-5, 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. 92276-38-5, name is 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine. A new synthetic method of this compound is introduced below.

General procedure: To a stirred solution of 6-bromo-1H-i,2,3-triazolo[4,5-b]pyridine (250 mg, 1.26 mmol) in DMF (5 mL) at rt was added 60% sodium hydride in mineral oil (55 mg, 1.38 mmol) and the mixture was stirred at rt for 30 mins. (2-(Chloromethoxy)ethyl)trimethylsilane (419 mg, 2.51 mmol) was added and the mixture was stirred for 15 h. The reaction mixture was partitioned between water and EtOAc and the aqueous layer was separated and further extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0 – 20% EtOAc in hexanes to afford a 1:1 mixture of 6-bromo- 1 -((2- (trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5-b]pyridine and 6-bromo-3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo[4,5 -b]pyridine (240 mg) as an oil, which was not purified further. LC-MS (ESI) mlz 329 and 331 (M+H).v [000223] Step 2: A 1:1 mixture of N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 – yl)-2-(4-(l -((2-(trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5 -b]pyridin-6- yl)phenyl)acetamide and N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)-2-(4-(3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo [4,5 -b]pyridin-6-yl)phenyl)acetamide (71 mg, 40%) was obtained as a solid using a procedure analogous to that described in Step 3 of Example4, substituting the product obtained from Step 1 of this example for the 2-chloro-6,7- dimethoxyquinoxaline used in Example 4 and substituting 2-(4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)acetamide (Ref: S. Abraham et al, WO 2011022473 Al) for the 2-(2-fluoro-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1 -(trifluoromethyl)cyclopropyl)isoxazol-3 -yl)acetamide used in Example 4. LC-MS (ESI) mlz 561 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; HOLLADAY, Mark, W.; LIU, Gang; ROWBOTTOM, Martin, W.; WO2015/31613; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 75279-39-9, name is N-(4-Aminopyridin-2-yl)acetamide. A new synthetic method of this compound is introduced below., Safety of N-(4-Aminopyridin-2-yl)acetamide

Step G 2,4-Diaminopyridine, dihydrochloride 4-Amino-2-acetylaminopyridine (150 mg, 1.0 mmol) was dissolved in 5 mL of concentrated aqueous ammonium hydroxide and heated in a glass pressure tube for 18 h at 100 C. The solvent was removed under reduced pressure and the residue dissolved in 3 mL of 2N HCl. The solvent was removed under reduced pressure and the product isolated by recrystallization from ethanol to give 102 mg of the bis hydrochloride salt. 1 H NMR (200 MHz, CD3 OD) delta 7.35 (bs, 1H); 6.12 (d, 1H, J=5 Hz); 5.79 (bs, 1H). Mass spectrum (FAB): m/e=110 (M+1).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 75279-39-9, N-(4-Aminopyridin-2-yl)acetamide.

Reference:
Patent; Merck & Co., Inc.; US5972975; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 77199-09-8, Adding some certain compound to certain chemical reactions, such as: 77199-09-8, name is Ethyl 5-bromopicolinate,molecular formula is C8H8BrNO2, 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 77199-09-8.

Under the protection of N2, PdCl2(dppf) (1.80 g, 0.0025 mol) was added to an anhydrous 1,4-dioxane (200 mL) solution of ethyl 5-bromo-2-picolinate (10.00 g, 0.043 mol), bis(pinacolato)diboron (12.20 g, 0.048 mol) and anhydrous potassium acetate (13.00 g, 0.13 mol), and the resulting mixture was heated to 100 C to react overnight. After cooling and concentration under reduced pressure, water and ethyl acetate were added to the residue, stirred for 15 min, and filtered through Celite, and the Celite was rinsed with ethyl acetate. After the filtrate was layered, the aqueous phase was extracted with ethyl acetate once. The ethyl acetate phases were combined, washed with a saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate, and concentrated to obtain a black residue, which was separated through a silica gel column (ethyl acetate/petroleum ether=1:10-1:2) to obtain a white solid product (9.03 g, 75%). 1H NMR (400 MHz, CDCl3,) delta 9.06 (d, J=1.6 Hz, 1H), 8.21 (dd, J=7.6 Hz, J=1.6 Hz, 1H), 8.10 (d, J=7.6 Hz, 1H), 4.48 (q, J=7.2 Hz, 2H), 1.45 (t, J=7.2 Hz, 3H), 1.37 (s, 12H).

According to the analysis of related databases, 77199-09-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; LI, Jijun; WU, Wei; ZHU, Yan; WANG, Huting; ZHAO, Lijia; HE, Weinan; SUN, Yinghui; PENG, Yong; HAN, Yongxin; (108 pag.)EP3412669; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 936011-17-5, 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. 936011-17-5, name is 5-Bromo-2-methoxyisonicotinaldehyde, molecular formula is C7H6BrNO2, 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 5-bromo-2-methoxypyridine-4-carbaldehyde (430 mg, 1.99 mmol), 4-(tributylstannyl)-1-(triphenylmethyl)-1H-imidazole (Intermediate A, 1800 mg, 3.0 mmol) and PdAMPHOS (142 mg, 0.20 mmol) in acetonitrile (20 mL) was stirred at 100 C. for 8 h under N2 atmosphere. The resulting reaction mixture was diluted with water (40 mL) and extracted with ethyl acetate (80 mL*2). The combined organic phase was washed with brine, and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with petroleum ether: ethyl acetate (7:3) to yield 2-methoxy-5-[1-(triphenylmethyl)-1H-imidazol-4-yl]pyridine-4-carbaldehyde (630 mg, 71%) as yellow solid. MS: m/z=446.0 [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 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; (167 pag.)US2016/75711; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 61830-40-8, name is 3,5-Dibromopicolinic acid, molecular formula is C6H3Br2NO2, 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. Computed Properties of C6H3Br2NO2

To n-butyllithium (2.5 M in hexane, 12 mL, 30 mmol) in THF (40 mL) at -78 C was added a solution of 3,5-dibromopicolinic acid (4.0 g, 14 mmol) in THF (60 mL) over 30 minutes. The reaction was stirred at -78 C for 1 hour after which DMF (11 mL, 144 mmol) was added dropwise. The cold bath was allowed to expire while stirring for 12 h. Water was added followed by IN HC1 (30 mL). The pH was adjusted to pH 3-4 using IN NaOH. The solution was extracted with EtOAc while maintaining a pH of 3 to 4. The combined organic layerswere washed with water and brine, dried (MgS04), filtered, and concentrated in vacuo to provide the title compound Ab2 that was carried on directly.

With the rapid development of chemical substances, we look forward to future research findings about 61830-40-8.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GILBERT, Eric, J.; CUMMING, Jared, N.; SCOTT, Jack, D.; WU, Wen-Lian; BURNETT, Duane, A.; STAMFORD, Andrew, W.; WO2014/150344; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211521-46-8, 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. 1211521-46-8, name is 2-Bromo-4-chloro-3-methylpyridine, molecular formula is C6H5BrClN, 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 2-bromo-3-methyl-4-chloro-pyridine (10.6 g, 57.1 mmol) in freshly distilled THF (120 mL) was cooled down to 0C and treated with isopropyl magnesium chloride (45.7 mL, 2.0 M in THF, 91.5 mmol). The resulting mixture was stirred at room temperature for 3 h then cooled to -5C. Cyclopropane carboxaldehyde (6.83 mL, 91.5 mmol) was added. The reaction mixture was stirred at room temperature for 1 h and quenched by adding water (100 mL), and extracted with ethyl acetate (2X150 mL). The organic phase was separated, dried, and concentrated. The residue was purified by flash silica column chromatography (hexane:ethyl acetate, 3:1) to afford the title compound as a yellow oil (7.01 g, 62%). ESI-MS m/z: 198 (M+H)+; 1H NMR (CDCl3, 300 MHz) delta ppm: 8.28 (d, J = 5.4 Hz, 1 H), 7.26 (d, J = 5.4 Hz, 1 H), 4.79 (d, J = 5.4 Hz, 1 H), 4.55 (br, s, 1 H), 2.39 (s, 3 H), 1.10-1.28 (m, 1 H), 0.58-0.41 (m, 4 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 1211521-46-8, 2-Bromo-4-chloro-3-methylpyridine.

Reference:
Patent; Emergent Product Development Gaithersburg Inc.; Roussel, Patrick; Heim, Jutta; Schneider, Peter; Bartels, Christian; Liu, Yaoquan; Dale, Glenn; Milligan, Daniel; (107 pag.)EP3034078; (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 1254073-41-0, name is 5-Fluoropicolinohydrazide. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 5-Fluoropicolinohydrazide

To a solution of 4-[(2,4-dichloro-3-fluorophenyl)carbonyl]-2-piperazinone (137) (0.146 g, 0.5 mmol) in Dichloromethane (DCM) (3 ml.) was added triethyloxonium tetrafluoroborate (0.100 g, 0.525 mmol). The solution was then stirred, under argon, for 10 minutes before 5-fluoro-2-pyridinecarbohydrazide (I24) (0.093 g, 0.600 mmol) was added. The solution was then stirred for a further hour before the solvent was concentrated and n-butanol (3.00 ml.) was added. The solution was then stirred, under argon and reflux, for 3 hours before being cooled to room temperature. The solvent was then evaporated in vacuo and the remaining residue was purified by flash chromatography (Biotage SP4, 25M cartridge) with a gradient of 0-10% 2M NH3/MeOH in DCM. TLC confirmed product location and the solvent from the combined fractions was evaporated in vacuo. The remaining residue was then further purified by mass-direct automated HPLC, and the solvent evaporated in vacuo. The remaining solid was then triturated with ether and dried in a vac-oven to yield the product in 0.045 g. LCMS: m/z = 409 (M+ H)+, retention time = 0.93 minutes (2 minutes)

With the rapid development of chemical substances, we look forward to future research findings about 1254073-41-0.

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALTER, Daryl Simon; WO2010/125102; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109613-97-0, Adding some certain compound to certain chemical reactions, such as: 109613-97-0, name is 2-Bromo-4-methoxypyridin-3-amine,molecular formula is C6H7BrN2O, 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 109613-97-0.

To an ice-cold solution of 2-bromo-4-methoxypyridin-3-amine (Intermediate 38), (2.74 g) in pyridine (102 mL) was added ethyl chloroformate (1.91 mL) dropwise and then stirred at rt for 45 min. The reaction mixture was cooled in an ice-bath and more ethyl chloroformate (9 mL) added and the mixture left to stir overnight at rt. The reaction mixture was diluted with EtOAc and washed with sat. aq. NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers washed with brine, dried over MgSO4, filtered and evaporated under vacuum to give a solid. Product was observed in the aqueous layer by LC-MS, so this was re-extracted with EtOAc (3*) and evaporated under vacuum to give a solid which was combined with the previous solid, dissolved in DCM and purified by column chromatography (normal phase, 50 g, Biotage SNAP cartridge KP-Sil, 50 mL/min, gradient 10-70% EtOAc in n-hexane) to give the desired product (2.35 g). LCMS: m/z 275.43 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.32 (t, J=7.1 Hz, 3H) 3.93 (s, 3H) 4.24 (q, J=7.1 Hz, 2H) 6.06 (br. s., 1H) 6.86 (d, J=5.6 Hz, 1H) 8.19 (d, J=5.6 Hz, 1H)

According to the analysis of related databases, 109613-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; PAYNE, Andrew; CASTRO PINEIRO, Jose Luis; BIRCH, Louise Michelle; KHAN, Afzal; BRAUNTON, Alan James; KITULAGODA, James Edward; SOEJIMA, Motohiro; WO2015/49574; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem