Day: May 21, 2021

Application of 504-24-5, 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. 504-24-5, name is 4-Aminopyridine. A new synthetic method of this compound is introduced below.

(1) Bromination reaction:In a 100 ml three-necked flask, 3.76 g (0.04 mol)4-aminopyridineAnd 0.04 g of azobisisobutyronitrile were dissolved in 36 ml of carbon tetrachloride,14.95g (0.084mol) of N-bromosuccinimide was added portionwise at 25 C, the reaction was carried out for 20h,After the liquid-phase central control monitored the conversion of 4-aminopyridine and intermediate 3-bromo-4-aminopyridine into the target product 3,5-dibromo-4-aminopyridine,The reaction mixture was cooled to room temperature with stirring, poured into 50ml carbon tetrachloride and stirred, filtered, the filter cake was washed twice with 2 × 30ml carbon tetrachloride, the filtrate was washed once with aqueous sodium bicarbonate solution, saturated salt Water once, spin-dried to remove carbon tetrachloride, and then recrystallized from petroleum ether,9.28 g of a white solid was obtained,Namely 3,5-dibromo-4-aminopyridine,Yield 92.10%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,504-24-5, 4-Aminopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Wohua Chemical Co., Ltd.; Hu Yadong; Yang Benmei; (5 pag.)CN106957259; (2017); A;,
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 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Bromo-1H-pyrrolo[2,3-b]pyridine

To a mixture of tert-butyl piperazine- 1-carboxylate (224 mg, 1.2 equiv.), 3-bromo-lH- pyrrolo[2,3-£]pyridine (197 mg, 1 equiv.), RuPhos (9.3 mg, 0.02 equiv.) and Ruphos Pd Gl, MTBE adduct (16.3 mg, 0.02 equiv.) in THF (2 mL), under argon atmosphere, a 1.3 M THF solution of LiHMDS (1.92 mL, 2.5 equiv.) was added. The resulting mixture was purged with argon for 5 min, and was then sealed in a vial and heated at 70 C for 3 h. The reaction mixture was cooled to RT, quenched by an addition of 1 M HC1 (1.5 mL), diluted with EtOAc and poured into a sat. solution of sodium bicarbonate. After extracting with 3 portions of EtO Ac, combined organic extracts were dried, and the solvent was removed in vacuo. The obtained residue was purified by flash chromatography on silica gel (eluting with a cyclohexane/EtOAc gradient, 0-100 % of EtO Ac) to afford the expected product (165 mg). LCMS: MW (calc’d): 302.4; MS (ES+, m/z): 303.2 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 74420-15-8.

Reference:
Patent; E-THERAPEUTICS PLC; JURKOVIC, Mihaela; LANDEK, Ivana Ozimec; POLJAK, Tanja; RO?CIC, Maja; STUBBERFIELD, Colin; VADLAMUDI, Srinivasamurthy; (228 pag.)WO2019/43372; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6959-47-3 , The common heterocyclic compound, 6959-47-3, name is 2-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, 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.

The ligand L3 was prepared by modifying an established method bySong et al. [24]. To a 100 mL round bottom flask, 15 mL of doubledistilled water was added, followed by an addition of 2-chloromethylpyridineHCl (4.96 g, 0.03 mol). Cyclohexylamine (1.73 mL,0.015 mol) was added dropwise to the mixture which was stirred for5 min before adding NaOH pellets (2.4 g, 0.06 mol). The mixture wasfurther stirred for 5 days at room temperature and the product was thenextracted with 3×30 mL portions of CHCl3. The organic layers werecombined and dried over MgSO4, yielding a crude product that waspassed through a silica column and eluted with CHCl3. The off-white crystalline solid obtained was isolated in moderate yield (1.8 g, 43%based on cyclohexylamine). 1H NMR (DMSO): delta 1.1 (m, 2H, CH2-cy),1.3 (q, 2H, J=11.1 Hz, CH2-cy), 1.5 (m, 2H, CH2-cy), 1.7 (m, 2H, CH2-cy), 1.8 (d, 2H, J=12.6 Hz, CH2-cy), 2.4 (m, 1H, CH2-cy), 3.8 (s, 4H,N-CH2-py), 7.2 (ddd, 2H, J=7.6, 3.9, 1.1 Hz, CH-py), 7.5 (d, 2H,J=7.6 Hz, CH-py), 7.7 (ddd, 2H, J=8.6, 7.8, 1.7 Hz, CH-py), 8.4 (d, 2H, J=4.9 Hz, CH-py). 13C NMR (DMSO): delta 24.4 (CH2-cy), 25.6 (CH2-cy), 25.7 (CH2-cy), 28.4 (CH2-cy), 32.9 (CH2-cy), 56.0 (N-CH2-py), 59.3(CH-cy), 121.8 (CH-py), 122.0 (CH-py), 136.3 (CH-py), 148.5 (CH-py),160.8 (C-py). IR numax (cm-1): 2923 (w), 2851 (w), 1587 (w), 1440 (w),1359 (s), 1127 (w), 754 (s), 620 (s). Melting point: 57.3-60.1 C. m/z[M+H]+ (calcd): 282.20 (282.40).

The synthetic route of 6959-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chanerika, Revana; Friedrich, Holger B.; Shozi, Mzamo L.; Inorganica Chimica Acta; vol. 495; (2019);,
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.109-04-6, name is 2-Bromopyridine, molecular formula is C5H4BrN, molecular weight is 157.996, as common compound, the synthetic route is as follows.Product Details of 109-04-6

General procedure: The general procedure for the preparation of N-(3-phenyl)-2,2-dichloroacetamide heterocyclic derivatives was as follows. A mixture of 1 mmol aryl(heterocyclic) bromide, 1.5 mmol 3-aminophenylboronic acid, 2 mmol K2CO3, Triphenyl phosphine at 0.4 mmol and palladium acetate at 0.1 mmol were stirred in 6 mL toluene and 6 mL ethanol at 60? under an argon atmosphere. The progress of the reaction was monitored by TLC (petroleum ether/ethyl acetate). After the reaction finished, the reaction mixture was filtered. The filtrate was concentrated to dryness and subjected to flash column chromatography (silica gel), eluting with petroleum ether/ethyl acetate, to give 3-aryl (hetero) aniline.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,109-04-6, 2-Bromopyridine, and friends who are interested can also refer to it.

Reference:
Article; Li, Tianwen; Yang, Yongchong; Cheng, Changmei; Tiwari, Amit K.; Sodani, Kamlesh; Zhao, Yufen; Abraham, Ioana; Chen, Zhe-Sheng; Bioorganic and Medicinal Chemistry Letters; vol. 22; 23; (2012); p. 7268 – 7271;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 94220-45-8 , The common heterocyclic compound, 94220-45-8, name is 5-Chloro-1H-pyrazolo[4,3-b]pyridine, molecular formula is C6H4ClN3, 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.

To a solution of 5-chloro-1H-pyrazolo[4,3-b]pyridine (500 mg, 3.29 mmol) in 1,4-dioxane (20 mL) and water (5 mL) were added (2-fluorophenyl)boronic acid (500 mg, 3.57 mmol), potassium phosphate (1.4 g, 6.5 mmol) and (2′-aminobiphenyl-2-yl)(chloro)(dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphoranylidene)palladium (100 mg, 0.127 mmol). The reaction was degassed and backfilled with N2 and stirred at 90 C. for 15 hours. After this time it was cooled to r.t., filtered and concentrated to dryness. The residue was purified by silica gel chromatography using 0-100% ethyl acetate in hexanes to afford desired product as yellowish oil (620 mg, 98%). LC-MS calculated for C12H9FN3 (M+H)+: m/z=214.2; found 214.2.

The synthetic route of 94220-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Liu, Kai; Pan, Jun; Sokolsky, Alexander; Vechorkin, Oleg; Ye, Hai Fen; Ye, Qinda; Yao, Wenqing; (75 pag.)US2018/72718; (2018); 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. 152460-10-1, name is N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine. This compound has unique chemical properties. The synthetic route is as follows. Safety of N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine

General procedure: The final target compounds were synthesized from 6-methyl-N-(4-(pyridin-3-yl) pyrimidin-2-yl) benzene-1,3-diamine 8(2 mmol), DMF (10 mL), and DIPEA (4 mmol) followed by substituted aromatic acid (2 mmol) was added and stirred at room temperature for 1 h. After completion of the reaction mixture was poured into ice-cold water. The obtained yellow precipitate washed with water and dried to get target titled product pyrimidine scaffold benzamide derivatives (9 a-k).

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, 152460-10-1, N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine.

Reference:
Article; Thirumurugan; Lakshmanan, Sivalingam; Govindaraj, Dharman; Daniel Prabu, D. Sam; Ramalakshmi; Arul Antony; Journal of Molecular Structure; vol. 1171; (2018); p. 541 – 550;,
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. 1597-33-7, name is 2-Fluoropyridin-3-amine. A new synthetic method of this compound is introduced below., name: 2-Fluoropyridin-3-amine

A solution of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 0.12 g, 0.34 mmol), EDC (0.16 g, 0.84 mmol) and HOBT (0.13 g, 0.84 mmol) in dimethy.formamide (2 ml) was stirred in air at room temperature for 1 h. 2-Fluoropyridin-3-amine (0.04 g, 0.37 mmol) was then added in one charge. The reaction mixture was stirred at 25 C overnight. Another batch of HOBT (0.13 g, 0.84 mmol), EDC (0. 61 g, 0.842 mmol) and 2-fluoropyridin~3-amine (0.04 g, 0.37 mmol) was added into the mixture and heating was continued at 40C for 38 hours. The reaction mixture was diluted with water (30 ml) and extracted with ethyl acetate (60 ml x 3). The organic phases were combined, washed with brine (50 ml x 3), dried over anhydrous MgS04l and concentrated. The residue was purified by chromatography (silica gel, 40 g, eluent: dichloromethane/methanol=50:1 , 1L). The solid was washed by methanol (3 ml x 2) and dried in vacuo to yield the title compound as a grey solid. 31 mg.1HNMR (400 MHz, DMSO-d6): 10.31 (s, 1 H), 8.64-8.61 (m, 3H), 8.26(d, 1 H, J=2.0), 8.04 (dd, 1H, J=2.4, 9.2), 7.97 (d, 1 H, J=4.8), 7.74 (dd, 2H, J=1.6, 4.8), 7.56 (d, 2H, J=7.2), 7.50(d,1 H, J=8.8), 7.43-7.36 (m, 4H), 5.42 (s, 2H).MS (electrospray): m/z [M+H]+ = 400.0

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, 1597-33-7, 2-Fluoropyridin-3-amine.

Reference:
Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (2011); 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.85838-94-4, name is tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate, molecular formula is C10H17NO2, molecular weight is 183.25, as common compound, the synthetic route is as follows.Formula: C10H17NO2

1′-(1-t-butoxycarbonyl-3-hydroxypiperidin-4-yl)-3,4-dihydro-spiro[naphthalene1(2H),4′-piperidine] (19c) and 1′-(1-t-butoxycarbonyl-4-hydroxypiperidin-3-yl)-3,4-dihydro-spiro[naphthalene-1(2H),4′-piperidine] (20c) A mixture of the hydrochloride of 10 (4.9 g, 20.6 mmol) and 5.8 g (21 mmol) of the isomeric bromohydrins derived from 1-t-butoxycarbonyl-l,2,3,6-tetrahydropyridine (see Procedure above) in absolute ethanol (25 mL) and triethylamine (15 mL) was refluxed for 24 h. Since TLC (silica gel, Hexanes/Ethyl acetate: 50/50) failed to show any progress in the reaction, solid potassium carbonate (7.26 g, 52.5 mmol) was added and the mixture was refluxed for four more days. After cooling, the salts were filtered off and the volatiles were removed under reduced pressure. The remaining brown oil was dissolved in ethyl acetate (30 mL) and the organic layer was successively washed with water (2*20 mL) and brine (20 mL), dried (Na2 SO4) and concentrated. The mixture of 19c and 20c was obtained as an orange oil (6.7 g, 84%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,85838-94-4, tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Regents of the University of Minnesota; US5457207; (1995); A;,
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.1620-76-4, name is 4-Methylpicolinonitrile, molecular formula is C7H6N2, molecular weight is 118.14, as common compound, the synthetic route is as follows.category: pyridine-derivatives

A solution of 2-cyano-4-methyl pyridine (0.15 g, 1.27 mmol) in about 10 mL of 6 M HCl was heated under reflux for 24 h. During this time, the initially light yellow solution changed to a clear solution. The solution was evaporated to dryness to leave a white solid. The solid was recrystallized from a minimal amount of distilled water to give a yield of 148 mg (85 %) . 1H NMR (DMSO-dff) : delta = 8.65 (IH, s), 8.06 (IH, s), 7.66 (IH, s) 2.05 (3H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1620-76-4, 4-Methylpicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; THE UNIVERSITY OF WARWICK; SADLER, Peter, John; PEACOCK, Anna, Frances, Acushla; VAN RIJT, Sabine, Helena; HABTEMARIAM, Abraha; WO2008/17855; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 524955-09-7, 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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. A new synthetic method of this compound is introduced below.

Following hydrogenation to form the first aniline intermediate, acid catalyzed coupling was performed to prepare 4-[3-chloro-4-(2-pyridylmethoxy)anilino]-3-cyano-7-ethoxy-6-N-acetylaminoquinoline, as shown below: To perform the coupling reaction, the two reactants were heated together in alcohol at 65-78 C. over 4-6 hours, yielding the product. The reaction begins as an amber slurry and thickens to a lighter beige slurry as it approaches completion. Upon scaling up from 75 g to 350 g, it proved necessary to add a catalytic amount (0.025 eq.) of methanesulfonic acid to initiate the reaction. As a specific example, 4-chloro-3-cyano-7-ethoxy-6-N-acetylaminoquinoline (0.141 kg, 0.49 mole) was added to the mixture of Example 2, followed by ethanol (0.037 L) to give a suspension. A catalytic amount of methanesulfonic acid (1.17 g) was added at 20-25 C. The resulting slurry was heated to 70-75 C. and held for a minimum of 4 hours. Thickening of the slurry was evident after 1.5 hours. Following reaction completion, the mixture was cooled to room temperature and may be used ?as is? in the telescoped reaction of Example 4 below.; As solvents EtOH, DMF or other suitable solvent may be used. Experimental results obtained using different solvents and reaction conditions are shown in Table 3. Difficulty filtering the product of this step (noted in several entries on Table 3) was circumvented by not isolating the solid at this point, but telescoping the reaction with the next step. It has been found that on the order of 20 volumes of EtOH were necessary to achieve reasonable stirring, but that the reaction can proceed in only 10 volumes of DMF, without significant loss in purity. In Table 3, where the entry is labelled NI, the intermediate product was not isolated, but carried into the next reaction step. TABLE 3 Coupling Reaction Coupling Temp Time Yield Solvent Solvent ( C.) (h) (%) Comments IPA EtOH 78 4 85.4 contains impurity THF EtOH 78 4 90.5 v. slow filtration THF THF 68 4 NA Only 16% product formed THF EtOH 78 4 94.2 v. slow filtration EtOH IPA 82 5 NA No reaction EtOH MeOH 65 5 60.0 v. slow filtration THF EtOH 78 1.5 80.3 v. slow filtration (MeSO3H) THF EtOH 78 4 86.0 v. slow filtration THF EtOH 78 3 85.7 4 h filtration – hard, green (MeSO3H) coated solid on drying THF Dimethoxy 85 2 74.2 Faster filtration (<1 hr) ethane Nice yellow solid THF Diethoxy 85 5 - - Methane THF Dimethoxy 70 6 - - Ethane THF EtOH 78 6 96.6 Slow filtration THF DMF 78 0.5 65.6 Some product lost in filtrate (MeSO3H) THF DMF 70 8 NI See Note 1 (MeSO3H) THF EtOH 78 6 ND See Note 2 (MeSO3H) THF EtOH 78 4 NI Yield to the free base is (MeSO3H) 80.4%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 83%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 86%3/ NR = no reaction, NI = not isolated; ND = not determined; NA = not available 1. Carried through to the deprotection and generation of free base to give 69.5% overall yield. 2. The overall yield after the deprotection and generation of the free base is 76.1% 3This reaction was not filtered at all but taken as slurry to the next step. At the same time, in my other blogs, there are other synthetic methods of this type of compound,524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, and friends who are interested can also refer to it. Reference:
Patent; WYETH; US2006/270668; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem