Tag: M.W:100-200

Synthetic Route of 71902-33-5 , The common heterocyclic compound, 71902-33-5, name is 3,5-Difluoropyridine, molecular formula is C5H3F2N, 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.

General procedure: An oven-dried reaction vessel (4 or 9 ml screw-cap vial) equipped with a stirring bar was allowed to cool to room temperature under vacuum. Activated 4 A molecular sieves (crushed, 50 mg), [Rh-2 ] (and solid substrates, 1.0 equiv.), were added under air. The vial was then depressurized and pressurized with argon gas three times before the addition of dry THF (1 M) (and liquid substrates, distilled over CaH2, 1.0 equiv.). Following the addition of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.0-4.0 equiv. as indicated), the glass vial was placed in a 150 ml stainless-steel autoclave under an argon atmosphere. The autoclave was pressurized and depressurized with hydrogen gas three times before the indicated pressure was set. The reaction mixture was stirred at 25-40 C for 24 h. After the autoclave was carefully depressurized, trifluoroacetic anhydride (3.0 equiv.) and CH2Cl2 (0.5 ml) were added to the crude mixture and stirring was continued for 10 min at room temperature. Alternatively, di-tert-butyl dicarbonate (3.0 equiv.), triethyl amine (3.0 equiv.) and CH2Cl2 (0.5 ml) were added to the reaction mixture and stirring was continued for 2 h at room temperature. The crude was then filtered over fritted funnel and the remaining solid was washed with ethyl acetate (2x 5 ml). The combined solution was concentrated under reduced pressure and submitted to column chromatography (pentane/ethyl acetate or pentane/dichloromethane) to obtain the final product. The indicated diastereoselectivities were determined by GC analysis or from the 19F NMR spectrum immediately after the reaction. NMR yield was calculated using hexafluorobenzene (20 mul, 0.173 mmol) as internal standard.

The synthetic route of 71902-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nairoukh, Zackaria; Wollenburg, Marco; Schlepphorst, Christoph; Bergander, Klaus; Glorius, Frank; Nature Chemistry; vol. 11; 3; (2019); p. 264 – 270;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 68963-75-7, 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. 68963-75-7, name is 4,6-Dichloropyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

2,4-Dichloro-6-hydroxypyridine (696mg, 4.2mmol), 3-exo-hydroxy-8- azabicyclo[3.2.1]octane-8-carboxylic acid terf-butyl ester (965mg, 4.2mmol) and (4,4- Dimethyl-1 ,1-dioxido-1 ,2,5-thiadiazolidin-2-yl)triphenylphosphonium (4.31g, 10.5mmol) in THF (2OmL) were stirred for 16h. Ethyl acetate (5OmL) and water (2OmL) were added and the organic and aqueous layers were separated. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was then purified by chromatography on silica gel. Elution with 10:90 ethyl acetate:heptane afforded 3-exo-(4,6-dichloropyridin-2- yloxy)-8-azabicyclo[3.2.1]octane-8-carboxylic acid terf-butyl ester (1.29g, 3.6mmol, 82percent). M.S. (ESI) m/z: 373,375 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,68963-75-7, its application will become more common.

Reference:
Patent; N.V. ORGANON; WO2007/63071; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 115170-40-6 ,Some common heterocyclic compound, 115170-40-6, molecular formula is C7H7BrN2, 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.

a) 30g (0.151mol) of 5-bromo-7-azaporphyrin, 60g of activated carbon fiber catalyst, 264g of xylene into the reaction flask, stirring evenly, to obtain a reaction mixture G;b) The reaction mixture G at 100 C, oxygen flow 200mL/min, reaction 8h, chromatographic monitoring of the disappearance of raw materials;c) Filtration, filter out activated carbon fiber catalyst, obtain organic layer H, recover solvent, get 5-bromo-7-azaindole crude product, recrystallize from methanol to obtain product 25.37g, yield 85.43%, content ?99% .

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. 115170-40-6, 5-Bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhonggang Group Anshan Heat Energy Institute Co., Ltd.; Wang Haiyang; Wang Shoukai; Xu Zhe; Zhao Wei; Jiang Hui; Jin Dan; Xu Haoran; (7 pag.)CN107987076; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 118289-17-1 ,Some common heterocyclic compound, 118289-17-1, molecular formula is C6H4BrNO, 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.

General procedure: To a 50 mL two-necked flask equipped with magnetic stirrer and condenser was added 2-bromopyridine (1.0 eq), Pd(PPh3)4 (5 mol%), K2CO3 solution (2.0 eq) and toluene under N2 at room temperture. After reacted for 15 min, a solution of the boronic acid (1.2 eq) in EtOH was then added. The reaction mixture was then heated to 95 C and reacted for 4 h. After cooling to room temperature, to the reaction mixture aqueous NH4Cl was added and extracted three times with EtOAc. The organic extracts were then combined, washed with brine, dried with MgSO4 and then concentrated under reduced pressure. The crude product was then purified by silica gel column chromatography(Petroleum ether/EtOAc) to give compounds 1 and 5

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,118289-17-1, its application will become more common.

Reference:
Article; Duan, Yingchao; Qin, Wenping; Suo, Fengzhi; Zhai, Xiaoyu; Guan, Yuanyuan; Wang, Xiaojuan; Zheng, Yichao; Liu, Hongmin; Bioorganic and Medicinal Chemistry; vol. 26; 23-24; (2018); p. 6000 – 6014;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 881-86-7, 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.881-86-7, name is Dimethyl pyridine-2,5-dicarboxylate, molecular formula is C9H9NO4, molecular weight is 195.17, as common compound, the synthetic route is as follows.

To a solution of dimethyl pyridine-2,5-dicarboxylate 21-a (13.0 g, 66.6 mmol) in a mixture of THF (110 mL) and ethanol (110 mL) was added calcium chloride (29.6 g, 266 mmol). After stirring at room temperature for 30 minutes, the reaction was cooled to 0C, and sodium borohydride (3.78 g, 100 mmol) was added portion wise. After the addition was completed the reaction was stirred at room temperature overnight. A saturated aqueous solution of ammonium chloride and dichloromethane were added, the organic layer was separated, and the aqueous phase was extracted twice with dichloromethane. The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to provide Intermediate 21-b as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 881-86-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PHARMASCIENCE INC.; LAURENT, Alain; ROSE, Yannick; WO2015/77866; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1001756-21-3, 4-Amino-6-chloronicotinaldehyde, 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, Recommanded Product: 4-Amino-6-chloronicotinaldehyde, blongs to pyridine-derivatives compound. Recommanded Product: 4-Amino-6-chloronicotinaldehyde

To a solution of 4-amino-6-chloro-pyridine-3-carbaldehyde (1.6 g, 10.2 mmol) (from Example 24 supra) in DMSO (10 mL) at room temperature, was added dimethyl malonate (6.4 g, 48.4 mmol) and DL-proline (1.5 g, 13 mmol) successively. The reaction mixture was stirred at room temperature for 16 hours and then at 65 C. for 2 hours. The mixture was poured into water (80 mL), and extracted with dichloromethane (4*100 mL). The organic phase was washed with water (3.*100 mL), brine (50 mL) and dried to give a crude product. It was purified by chromatography (silica gel, 200-300 mesh, eluting with a mixture of petroleum ether and ethyl acetate (3:2, v/v)) to give 7-chloro-2-oxo-1,2-dihydro-[1,6]naphthyridine-3-carboxylic acid methyl ester. (Yield 2.0 g, 82.3%). 1H NMR (300 MHz, DMSO): delta 12.41 (s, 1H), 8.86 (s, 1H), 8.64 (s, 1H), 7.22 (s, 1H), 3.83 (s, 3H). LC-MS: [M+H]+ 239.0.

The synthetic route of 1001756-21-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Luk, Kin-Chun; US2012/184562; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 52378-64-0, 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. 52378-64-0, name is (3-Bromopyridin-2-yl)methanol. A new synthetic method of this compound is introduced below.

Intermediate 6 3-Bromo-2-(5-chloro-2-iodo-phenoxymethyl)-pyridine Alternate Alkylation Method:(3-Bromo-pyridin-2-yl)-methanol (7.39 g, 39.30 mmoles), and triethylamine (7.15 mL, 51.3 mmoles) are combined in tetrahydrofuran (70 mL) under nitrogen. The solution is chilled to 0.6 C. with an ice bath. Methanesulfonyl chloride (3.35 mL, 43.28 mmol) is added dropwise over 20 min, controlling the exotherm such that the internal temperature does not exceed 5 C. Following the addition, the reaction is stirred over an ice bath. After 20 min HPLC analysis shows that the (3-Bromo-pyridin-2-yl)-methanol is fully consumed. Triethylamine hydrochloride is filtered using a fitted glass funnel, washing with cold THF (50 mL). The THF filtrate containing the mesylate is placed under nitrogen and chilled in an ice bath. 2-Iodo-5-chlorophenol (10.00 g, 39.30 mmoles) is added, followed by addition of sodium t-butoxide (4.10 g, 41.38 mmol) in two equal portions with a mild exotherm of about 5 C. for each addition. The ice bath is removed and the reaction allowed to stir overnight. The reaction is quenched with water (50 mL) and the lower aqueous layer allowed to slowly separate. The organic portion is washed with brine (25 mL), and then the brine and aqueous portions back-extracted with THF (10 mL). The organic portions are combined and dried over sodium sulfate, filtered, and concentrated to afford a rusty orange solid. The solid is dissolved in dichloromethane (25 mL) and chromatographed on an AnaLogix Inc., Intelliflash 180 automated chromatography instrument, version 1.8.0. using a gradient of 10-20% ethyl acetate/hexanes over 35 min to afford 11.0 g (65%) of the product as a yellow solid. 1H NMR (DMSO) delta 5.31 (2H, s), 6.85 (1H, dd), 7.25 (1H, m), 7.39 (1H, dd), 7.77 (1H, d), 8.17 (1H, d), 8.59 (1H, d).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52378-64-0, (3-Bromopyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; US2010/69425; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3222-48-8, name is 5-Cyano-2-picoline. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H6N2

To a solution of 6-methylpyridine-3-carbonitrile (10.5 g, 25.7 mmol) in MeOH (80 mL) and NHs/MeOH (20 mL, 7 M) was added Raney-Ni (2.0 g) under N2 atmosphere. The suspension was degassed in vacuo and refilled with H2. The mixture was stirred for 12 hrs at 40 C under H2 (50 psi) atmosphere. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give (6-methyl-3-pyridyl)methylamine (9.5 g, compound 34b) as a light oil. 1H NMR (400 MHz, DMSO- d6) delta ppm: 8.36 (s, 1H), 7.62 (d, 7 = 8.0 Hz, 1H), 7.18 (d, / = 8.0 Hz, 1H), 3.69 (s, 2H), 2.42 (s, 3H). MS obsd. (ESI+) [(M+H)+]: 123.

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, 3222-48-8, 5-Cyano-2-picoline.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; LIANG, Chungen; MIAO, Kun; WANG, Jianping; YUN, Hongying; ZHENG, Xiufang; (230 pag.)WO2016/180695; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 127406-56-8, name is 4-Pyridin-2-yl-benzaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4-Pyridin-2-yl-benzaldehyde

To a solution of 3, 4, 5-piperidinetriol, 2- (hydroxymethyl)-, (2S, 3R, 4R, [5S)] [(50MG,] 0. [31MMOL)] in methanol [(2ML)] was added 4- (2-pyridyl) benzaldehyde (280mg, 1. [53MMOL).] The mixture was stirred for 5 min until fully dissolved. The pH was adjusted to 5 by addition [OF METHANOLIC HCI (1M),] then (polystyrylmethyl) trimethylammonium cyanoborohydride (180mg, 0. [78MMOL)] was added. The resultant mixture was stirred at room temperature for 48 [H.] The crude reaction mixture was purified using a plug of acidic Dowex 50X4-200 resin [(1.] [5G),] which had been pre-washed with 10% aqueous hydrochloric acid, followed by water then methanol. The resin was eluted with methanol [(25ML)] to remove all non-basic side products. The desired compound was then eluted using a solution of 2: 2: 1 [METHANOL/WATER/AMMONIUM] hydroxide [(50ML).] The solution was concentrated to a small volume [(~LML)] and freeze dried. The resulting residue was crystallised from [METHANOL/ETHYL] acetate to give the title product (80mg, [78%).’H] NMR (d4-methanol) 8 2.63 [(1H,] dd, [J =] 9.6, 12. [2 HZ),] 2.73 [(1H,] dd, J = 5.1, 12. [2 HZ),] 3.11 [(1H,] m), 3.40 [(1H,] t, J [= 9.] 0 Hz), 3.53 [(1H,] m), 3.78 [(1H,] dd, J = 5.3, 9.0 Hz), 3.88-4. 03 (4H, m), 7.35 [(1H,] m), 7.50 [(2H,] d, J [= 8.] 3 Hz), 7.82-7. 90 (4H, m), 8.59 [(1H,] d, J = 4.9 Hz). MS [M/Z] 331.3 (M+H) +.

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, 127406-56-8, 4-Pyridin-2-yl-benzaldehyde.

Reference:
Patent; OXFORD GLYCOSCIENCES (UK) LTD; WO2004/7453; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 170886-13-2, 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. 170886-13-2, name is 2-(Trifluoromethyl)pyridin-4-ol. A new synthetic method of this compound is introduced below.

A mixture of 2-(trifluoromethyl)pyridin-4-ol (100 mg, 0.613 mmol) and Lawesson?s reagent (123.99 mg, 0.307 mmol) in toluene (10 mL) was refluxed for 2 hours. Excess solvent was evaporated under reduced pressure. The residue was purified by automate column chromatography to give the desired product (75 mg, 68% yield). LC-MS: m/z: 180 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,170886-13-2, 2-(Trifluoromethyl)pyridin-4-ol, and friends who are interested can also refer to it.

Reference:
Patent; HELMHOLTZ-ZENTRUM FUeR INFEKTIONSFORSCHUNG GMBH; AHMED, Ahmed S. A.; EMPTING, Martin; HAMED, Mostafa; HARTMANN, Rolf W.; HAUPENTHAL, Joerg; HASTERKAMP, Thomas; KAMAL, Ahmed A. M.; MAURER, Christine K.; ROeHRIG, Teresa; SCHUeTZ, Christian; YAHIAOUI, Samir; ZENDER, Michael; (128 pag.)WO2020/7938; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem