Month: April 2022

Electric Literature of 18699-87-1 ,Some common heterocyclic compound, 18699-87-1, 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.

Add to a 3 neck flask containing 500 mL of absolute ethanol under N2, 2.2 g (0.0956 g-atom) of sodium. After all the sodium reacts, add diethyl oxalate (98 mL) dropwise, and then add compound 2a-1 (one equivalent). The color turns from light yellow to brown upon addition. Allow the resulting solution to stand for two days at rt. Treat the orange mixture with SN HCl (pH=1), collect the precipitate by filtration and wash the filter cake with 100 mL EtOH and 200 mL di-isopropyl ether to afford 3a-1 as 2-hydroxy-3-(3-nitro-pyridin-2-yl)-acrylic acid ethyl ester (R4H, 20 g, 86%) or its tautomeric ketoester or as a mixture of keto-enol tautomers. 1H NMR (DMSO-d6) delta 8.83 (dd, 1H, J=1.1, 5.0 Hz), 8.65 (dd, 1H, J=1.5, 8.4 Hz), 7.56 (dd, 1H, J=5.0, 8.4 Hz), 7.11 (s, 1H), 3.47 (bs, 1H), 4.28 (q, 2H, J=7.1 Hz), 1.30 (t, 3H, J=7.0 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18699-87-1, its application will become more common.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US2005/131012; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1206775-52-1 ,Some common heterocyclic compound, 1206775-52-1, 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.

(2) Tetrakistriphenylphosphine palladium (403 mg), phenylboronic acid (510 mg) and a 2 M sodium carbonate solution (3.5 mL) were sequentially added to a solution of 5-bromo-6-methoxypyridine-2-carbaldehyde (753 mg) in 1,2-dimethoxyethane (23 mL) in a nitrogen atmosphere, and the mixture was stirred at 80 C. for three hours. Water was added to the reaction solution at room temperature, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1?1:1) and further purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to give 6-methoxy-5-phenylpyridine-2-carbaldehyde (445 mg, 60%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1206775-52-1, its application will become more common.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD.; US2011/237791; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 117519-13-8, 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. 117519-13-8, name is 6-Chloro-2-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, 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.

Step 3: 6-Chloro-2-(trifluoromethyl)pyridine-3-sulfonyl chloride (P73c) Step (a): Thionyl chloride (42 mL) was added dropwise under ice cooling over 60 min to water (250 mL) maintaining the temperature of the mixture at 0-7C. The solution was allowed to warm to 18C and stirring was continued for 3 d. CuCI (151 mg) was added to the mixture and the resultant yellow-green solution was cooled to -3C using an acetone/ice bath. Step (b): Hydrochloric acid (36% w/w, 12.2 mL) was added with agitation to compound P73b (1.65 g, 8.4 mmol), maintaining the temperature of the mixture below 30C with ice cooling. The mixture was cooled to -5C using an ice/acetone bath and a solution of sodium nitrite (0.68 g, 9.8 mmol) in water (2.8 mL) was added dropwise over 30 min maintaining the temperature of the mixture between -5 to 0C. The resultant slurry was cooled to -2C and stirred for 10 min. Step (c): The slurry from step (b) was cooled to -5C and added to the solution obtained from step (a) over 95 min, maintaining the temperature of the mixture between -3 to 0C (the slurry from step (b) was maintained at -5C throughout the addition). As the reaction proceeded, a solid began to precipitate. When the addition was complete, the mixture was agitated at 0C for 75 min. The solid was collected by vacuum filtration, washed with ice-cooled water (2x 25 mL) and dried under vacuum at below 25C to give compound P73c (1.53 g, 66%) as yellow solid. H-NMR (CDCI3, 300 MHz) delta: 7.81 (1 H, d, J = 8.4 Hz), 8.57 (1 H, d, J = 8.4 Hz).

According to the analysis of related databases, 117519-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2013/79223; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 86521-05-3, 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 86521-05-3, name is 2-((Trimethylsilyl)ethynyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

a) 2-Ethynyl-pyridine A solution of 2-trimethylsilanylethynyl-pyridine (3.05 g, 14 mmol) in MeOH (8.5 mL) was added dropwise to potassium hydroxide solution (1 N, 14 mL) and the reaction mixture was stirred at room temperature for 1 h and then acidified with HCl (3 N, 8.5 mL) and the mixture concentrated. The residue was then diluted with water and make alkaline with solid sodium carbonate, extracted with diethyl ether and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, diethylether) afforded the title compound (1.3 g, 75%) as a brown liquid. MS: m/e=176.0 [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 86521-05-3, 2-((Trimethylsilyl)ethynyl)pyridine.

Reference:
Patent; Hernandez, Maria-Clemencia; Lucas, Matthew C.; Thomas, Andrew; US2012/115844; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1231930-13-4, 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. 1231930-13-4, name is 3-Bromo-2-methyl-6-nitropyridine, molecular formula is C6H5BrN2O2, 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 Example A6 (1.7 g, 6.40 mmol) in dioxane (30 mL) was sparged with Ar, treated with acetamide (1.512 g, 25.6 mmol), Cs2CO3 (2.085 g, 6.40 mmol), X-Phos (0.153 g, 0.320 mmol) and Pd2(dba)3 (0.293 g, 0.320 mmol) and heated at 80 C. for 20 h. The mixture was cooled to RT, treated with EtOAc, the solids removed via filtration through diatomaceous earth and rinsed well with EtOAc. The filtrate was washed with water, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/DCM) to afford N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (450 mg, 24%) as a light yellow solid. MS (ESI) m/z: 289.1 (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 1231930-13-4, 3-Bromo-2-methyl-6-nitropyridine.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Samarakoon, Thiwanka; Caldwell, Timothy Malcolm; Vogeti, Lakshminarayana; Ahn, YuMi; Patt, William C.; Yates, Karen M.; US2014/315917; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 169280-83-5, tert-Butyl (5-(hydroxymethyl)pyridin-2-yl)carbamate, 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 C11H16N2O3, blongs to pyridine-derivatives compound. Computed Properties of C11H16N2O3

Production Example 1 To a mixture of tert-butyl [5-(hydroxymethyl)pyridine-2-yl]carbamate (2.13 g), triethylamine (5.3 ml), and DMSO (15 ml), a sulfur trioxide-pyridine complex (3.02 g) in a DMSO solution (15 ml) was added dropwise, followed by stirring at room temperature for 4.5 hours. To the reaction mixture, water was added, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After removing the desiccant, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 2.00 g of tert-butyl (5-formylpyridin-2-yl)carbamate.

The synthetic route of 169280-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; EP2216330; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 139585-48-1, Adding some certain compound to certain chemical reactions, such as: 139585-48-1, name is 2-Chloro-5-methoxypyridine,molecular formula is C6H6ClNO, 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 139585-48-1.

(Step 3) Preparation of methyl 2-[(2-methoxyethoxy)methoxy]-3-(5-methoxypyridin-2-ylamino)benzoate To a solution of 3-amino-2-((2-methoxyethoxy)methoxy)benzoic acid methyl ester 1.25 g (4.9 mmol) of step 2 in 1,4-dioxane 10 mL were added 2-chloro-5-methoxypyridine 0.70 g (4.9 mmol), Pd(OAc)2 0.11 g (0.49 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 0.31 g (0.49 mmol) and Cs2CO3 3.85 g (9.8 mmol), followed by stirring at 90 C. for 12 hrs. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, diluted with ethylacetate, and washed with a saturated sodium bicarbonate solution and a saturated NaCl solution. After drying over magnesium sulfate and concentration in a vacuum, purification by column chromatography (developing solvent: ethylacetate/hexane=1/2) afforded 1.2 g of the title compound (yield 68%).

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. 139585-48-1, 2-Chloro-5-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Daewoong Pharmaceutical Co., Ltd.; US8026235; (2011); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1147422-00-1 ,Some common heterocyclic compound, 1147422-00-1, molecular formula is C12H22N2O2, 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.

1-Methyloctahydro-1H-pyrrolo[3,2-c]pyridine To a solution of tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (1.05 g, 4.64 mmol, Shah, S. K et. al, Bioorg. Med. Chem. Lett. 2005, 15, 977-982) in DCM (20 mL) was added TEA (1.29 mL, 9.29 mmol) followed by dropwise addition of benzyl chloroformate (0.795 mL, 5.57 mmol) at ambient temperature. After about 4 h, the mixture was diluted with DCM and then washed with water and brine. The organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with a gradient of 0-75% EtOAc in heptane to give 5-benzyl 1-tert-butyl hexahydro-1H-pyrrolo[3,2-c]pyridine-1,5(6H)-dicarboxylate (1.05 g, 63% yield): LC/MS (Table 1, Method a) Rt=2.59 min; MS m/z: 361 (M+H)+.

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. 1147422-00-1, tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; US2011/152243; (2011); 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 1159812-31-3, name is 7-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1159812-31-3

To 7-bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine (2.14 g, 10.09 mmolAnd benzophenone imine (2.75g, 15.17mmol)In a solution of 1,4-dioxane (40 mL),Add Pd2(dba)3 (467.0 mg, 0.51 mmol),BINAP (95%, 664.4 mg, 1.01 mmol)And t-BuONa (1.94 g, 20.19 mmol).The reaction system was stirred at 100 C overnight.It was then cooled to room temperature and concentrated under reduced pressure.The residue obtained was purified by silica gel column chromatography (MeOH / DCThe title compound was obtained as a yellow solid (2.56 g, yield: 81.2%).

With the rapid development of chemical substances, we look forward to future research findings about 1159812-31-3.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Peng Ju; Li Xiaobo; Zhang Tao; Hu Haiyang; Chen Wuhong; Bai Changlin; Ke Donghua; Chen Peng; (217 pag.)CN109776522; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-35-3, Adding some certain compound to certain chemical reactions, such as: 884494-35-3, name is 2-Chloro-5-fluoropyridin-3-ol,molecular formula is C5H3ClFNO, 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 884494-35-3.

Preparation 222 2-chloro-5-fluoro-3-methoxypyridine 2-chloro-5-fluoro-3-methoxypyridine (1.8 g, 72%) was prepared in an analogous manner to Preparation 153 using 2-chloro-5-fluoropyridin-3-ol (2.3 g, 16 mmol) and methanol (5 g, 156 mmol). 1H NMR (CDCl3, 400 MHz): delta 7.89 (d, J=2.70 Hz, 1H), 7.00 (dd, J=2.5, 9.1 Hz, 1H), 3.93 (s, 3H).

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. 884494-35-3, 2-Chloro-5-fluoropyridin-3-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; Strohbach, Joseph Walter; Akama, Tsutomu; Blakemore, David Clive; Jacobs, Robert Toms; Jones, Peter; Limburg, David Christopher; Oderinde, Martins Sunday; Perry, Matthew Alexander; Plattner, Jacob John; Torella, Rubben Federico; Zhou, Yasheen; Yeoh, Thean Yeow; (200 pag.)US2020/108083; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem