Category: pyridine-derivatives

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. 10128-91-3, name is Methyl 2-oxo-1,2-dihydro-3-pyridinecarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 10128-91-3

(b) Methyl 2-hydroxy-5-iodonicotinate. A solution of methyl2-hydroxynicotinate (100 g, 0.65 mol) and N-iodosuccinimide (192 g, 0.85 mol) in dry DCM (2.5 L) was heated at reflux in the dark for 48 hours. The mixture was concentrated to 500 mL under reduced pressure. The solid which precipitated was collected by filtration, washed with small portions of cold DCM, and dried in vacuo to give the title compound as a pale-yellow solid.

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, 10128-91-3, Methyl 2-oxo-1,2-dihydro-3-pyridinecarboxylate.

Reference:
Patent; AMGEN INC.; WO2008/130600; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 117519-09-2, 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.117519-09-2, name is 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.

A mixture of compound 2-chloro-6-(trifluoromethyl)pyridin-3-amine (5.88g, 30mmol, prepared as described in WO 20091 10475), isoamyl nitrite (7.02g, 60mmol), p-TsOH (6.19g, 36mmol), TBAB (19.32g, 60mmol) and CuBr2 (1 .40g, 6mmol) in 60ml of MeCN was stirred at room temperature for 4h. Then, the mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel to give the title compound (5.85g, 75%). 1H-NMR (300Mz, DMSO-d6): delta 7.85 (d, 1 H), 8.52 (s, 1 H); 19F-NMR (300Mz, DMSO-d6): delta -65.72 (s, 3F).

Statistics shows that 117519-09-2 is playing an increasingly important role. we look forward to future research findings about 3-Amino-2-chloro-6-(trifluoromethyl)pyridine.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; EDMUNDS, Andrew; MUEHLEBACH, Michel; STOLLER, Andre; LOISELEUR, Olivier; BUCHHOLZ, Anke; HUETER, Ottmar Franz; BIGOT, Aurelien; HALL, Roger Graham; EMERY, Daniel; JUNG, Pierre Joseph Marcel; LU, Long; WU, Yaming; CHEN, Ruifang; WO2015/715; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55589-47-4 ,Some common heterocyclic compound, 55589-47-4, molecular formula is C7H7NO, 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.

Step D – 4- (5-(l-(6-methoxypyrimidine-4-yI)-8-f(3-methgammalpgammaridin~2~yl) methyll-2, 4-dioxo-l, 3, 8- triazaspiroN. 51 dec-3-yI| pyridin-2-gammal) benzoic acid, (10-1) A suspension of Compound 10-C (0.9 mmol), triacetoxyborohydride (2.09 mmol) and 3- methylpyridine-2-carboxaldehyde (1.43 mmol) in dry methylene chloride was treated with acetic acid (2.85 mmol) and stirred at ambient temperature over night. The mixture was diluted with methylene chloride and water and the pH was adjusted to pH 7 with 1 N NaOH. The layers were separated and the aqueous layer washed (x2) with methylene chloride. The combined organic layers was dried (MgSClambdai) and concentrated. Reverse Phase HPLC purification (Method C) afforded the title Compound 10-D (Example 10-1) as a salt of trifluoroacetic acid; 1H NMR(DMSO): delta = 13.05 -13.43 (b, 1H), 10.15-10.29 (b, 1H), 8.85 (s, 1H), 8.79 (s, 1H), 8.53 (s, 1H), 8.26-8.29 (m, 3H), 8.08-8.12 (m, 3H), 7.76 (d, J= 7.7 Hz, 1H), 7.55 (s, 1H), 7.39-7.42 (m, 1H), 4.73 (s, 2H), 3.98 (s, 3H), 3.78 (m, 2H), 3.66 (m, 2H), 3.52-3.58 (m, 2H), 2.52 (m, 2H), 2.37 (s, 3H). LCMS (Method A): 1.58 min, m/z (MH)+ = 580.1.

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. 55589-47-4, 3-Methylpicolinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PIERCE, Joan, M.; HALE, Jeffrey, J.; MIAO, Shouwu; VACHAL, Petr; WO2010/147776; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1214334-70-9 ,Some common heterocyclic compound, 1214334-70-9, molecular formula is C7H6BrNO3, 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.

5-bromo-6-methoxy-N,N-dimethylpicolinamide (0305) To a solution of 5-bromo-6-methoxypyridine-2-carboxylic acid (1.0 g, 4.31 mmol) in DMF (10 mL) were added dimethylamine (1.5 g, 33.27 mmol), HATU (2.0 g, 5.13 mmol) and DIEA (1.7 g, 12.77 mmol) at room temperature. The resulting solution was stirred for 2 h at 100 C. The reaction mixture was cooled to room temperature and treated with water (50 mL). The resulting mixture was extracted with ethyl acetate (100 mL×3). The organic phases were combined, washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to yield 5-bromo-6-methoxy-N,N-dimethylpyridine-2-carboxamide as black oil (1.2 g, crude). MS: m/z=259.0 [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,1214334-70-9, its application will become more common.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); 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

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

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

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

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

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