Category: pyridine-derivatives

Electric Literature of 86847-84-9 ,Some common heterocyclic compound, 86847-84-9, molecular formula is C10H13ClN2O, 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 solution of iert-BuLi (1.7 M in pentane) was slowly added over half hour to a solution of compound 13-2 (1.25 g, 5.91 mmol) in anhydrous THF at -78 C. After the reaction was stirred for 3 h at -78 C, a solution of iodine (1.8 g, 7.09 mmol, 1.2 equiv.) in THF was added and the reaction mixture was allowed to warm up to room temperature and stirred for 14 h. The reaction was concentrated and the residue diluted with methylene chloride. The organic layer was washed sequentially with 10% aqueousNa2S203 and NaHC03 and concentrated under reduced pressure. The product was purified by flash chromatography using Combiflash and employing a gradient of 0-20% EtOAc in Hexanes to afford 1.50 g (4.45 mmol, 73% yield) of 13-3.

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. 86847-84-9, N-(6-Chloropyridin-2-yl)pivalamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FENG, Yangbo; CHEN, Yen Ting; SESSIONS, Hampton; MISHRA, Jitendra K.; CHOWDHURY, Sarwat; YIN, Yan; LOGRASSO, Philip; LUO, Jun-Li; BANNISTER, Thomas; SCHROETER, Thomas; WO2011/50245; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 81803-60-3, 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.81803-60-3, name is Ethyl imidazo[1,5-a]pyridine-3-carboxylate, molecular formula is C10H10N2O2, molecular weight is 190.2, as common compound, the synthetic route is as follows.

To a solution of ethyl imidazo[1,5-a]pyridine-3-carboxylate (152 mg) in Acetic Acid (0.25M) was added Bromine (leq). The reaction was stirred at room temperature for 5 minutes thenconcentrated to dryness to give 205 of the title compound. This intermediate was taken onto the next step without purification.

The chemical industry reduces the impact on the environment during synthesis 81803-60-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 56057-19-3 , The common heterocyclic compound, 56057-19-3, name is 6-Chloro-5-nitro-2-picoline, molecular formula is C6H5ClN2O2, 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.

C. 2-Phenyl-5-nitro-6-methylpyridine A mixture of Compound B and 2-chloro-3-nitro-6-methylpyridine (0.42 g, 2.40 mmol) in THF (10 mL) was degassed with nitrogen. Tetrakistriphenylphosphine palladium (28 mg, 0.024 mmol) was added and the mixture was stirred 30 minutes. 25 Phenylboronic acid (0.44 g, 3.6 mmol) and 2M Na2 CO3 (1.8 mL) were added and the mixture was heated at 75 C. for 17 hours and stirred at room temperature for 48 hours. Methylene chloride was added and the mixture was filtered through celite and partitioned. The mixture was washed with saturated aqueous NaHCO3, dried (magnesium sulfate), filtered and evaporated to afford 0.77 g of brown solid. Flash chromatography (silica, 10% ethyl acetate/hexanes) afforded 0.37 g of Compound C (72%) as an off white solid and 0.05 g of 2-phenyl-3-nitro-6-methylpyridine (10%) as an oil.

The synthetic route of 56057-19-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US6011029; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 718608-10-7 , The common heterocyclic compound, 718608-10-7, name is 5-(Bromomethyl)-2-methylpyridine hydrobromide, molecular formula is C7H9Br2N, 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 mixture of 8-chloro-3-((1S,2S)-2-hydroxycyclohexyl)-6-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)quinazolin-4(3H)-one (130 mg, 0.321 mmol), cesium carbonate (314 mg, 0.964 mmol) and 5-(bromomethyl)-2-methylpyridine hydrobromide (103 mg, 0.385 mmol) in THF (5.0 ml) was sparged under nitrogen for 5 minutes. The mixture was treated with [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (26.2 mg, 0.032 mmol), sparged under nitrogen (3 minutes) and then heated at 60 C for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (25 mL) and water (25 mL), and extracted with ethyl acetate (3 x 25 mL). The combined organic extracts were washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (90:10 to 0:100; water containing 0.1% formic acid : acetonitrile containing 0.1% formic acid) to yield the title compound. 1H NMR (400MHz, CD3OD): delta 8.35 (d, J = 2.0 Hz, 2H), 8.02 (d, J = 1.6 Hz, 1H), 7.80 (d, J = 2.0 Hz, 1H), 7.62 (d, J = 8.0, 2.0 Hz, 1H), 7.27 (d, J = 8.0 Hz, 1H), 4.51- 4.49 (m, 1H), 4.13 (s, 2H), 4.07- 4.02 (m, 1H), 2.51 (s, 3H), 2.20- 2.10 (m, 1H), 1.97- 1.84 (m, 4H), 1.48- 1.46 (m, 3H) ppm. LRMS C21H23ClN3O2: calc?d 384.1, obs 384.2 (M+H) +.

The synthetic route of 718608-10-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; MOHANTY, Subhendu Kumar; LATTHE, Prashant R.; KUDUK, Scott D.; HOYT, Scott B.; (107 pag.)WO2017/155816; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 22282-70-8, 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.22282-70-8, name is 2-Fluoro-4-iodopyridine, molecular formula is C5H3FIN, molecular weight is 222.99, as common compound, the synthetic route is as follows.

Example 75A 2-Amino-4-iodopyridine A mixture of 2-floro-4-iodopyridine (3.0 g, 13.5 mmol), acetylamide (15.8 g, 269 mmol) and potassium carbonate (9.2 g, 67 mmol) was stirred at 180 C. for 7 hours, poured into ice (100 g), extracted with ethyl acetate, washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexane to provide the title compound (1.1 g, 37%). MS (DCI/NH3) m/e 221 (M+H).

The chemical industry reduces the impact on the environment during synthesis 22282-70-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 696-42-4, 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 696-42-4, name is 5-Fluoronicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

[0307] Cesium carbonate (0.734 g, 2.25 mmol) and 5-chloro-3-methylpyridine-2-carbonitrile (0.206 g, 1.35 mmol) wereadded at room temperature to a suspension of the optically active form of cis-1-(diphenylmethyl)-5-hydroxy-3-(piperidin-4-yl)-4-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one (0.212 g, 0.451 mmol) produced in ReferenceExample 27 in DMSO (2 mL), and the mixture was stirred at 150C for 2 hours. The reaction suspension wascooled to room temperature, then diluted with ethyl acetate, and washed with brine. The obtained organic layer wasdried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residuewas purified by silica gel column chromatography [elute: hexane/ethyl acetate = 92/8 – 50/50 (gradient)] to obtain thetitle compound (0.226 g, yield: 86%, optically active form:_[0327] The title compound (42.7 g, yield: 70%, optically active form) was obtained through reaction at 80C for 1 hourand then at 100C for 5 hours by the method described in Reference Example 30 using 5-fluoropyridine-3-carbonitrile(26.0 mg, 0.213 mmol) instead of 5-chloro-3-methylpyridine-2-carbonitrile.[0328] 1H-NMR (400MHz, CDCl3) delta: 8.46 (1H, d, J=3Hz), 8.25 (1H, d, J=2Hz), 7.43-7.04 (10H, m), 6.91 (1H, s), 6.71(1H, s), 4.56-4.51 (1H, m), 3.96-3.86 (1H, m), 3.83-3.73 (2H, m), 3.72-3.67 (1H, m), 3.02-2.93 (2H, m), 2.87-2.76 (1H,m), 2.08-1.85 (4H, m).

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 696-42-4, 5-Fluoronicotinonitrile.

Reference:
Patent; Daiichi Sankyo Company, Limited; KOBAYASHI, Hideki; ARAI, Masami; KANEKO, Toshio; TERASAKA, Naoki; (95 pag.)EP3081566; (2016); 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.79055-59-7, name is 2-Bromo-6-methylpyridin-4-amine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.name: 2-Bromo-6-methylpyridin-4-amine

Lithium bis(trimethylsilyl)amide in THF (4.63 mL, 1 M, 4.63 mmol) was added to ethyl 3-fluoro- 1 -methyl-4-[[ 1 -(trifluoromethyl)cyclobutyl]sulfamoyl]pyrrole-2-carboxylate (492.4 mg, 1.322 mmol) and 2-bromo-6-methylpyridin-4-amine (371.0 mg, 1.98 mmol) in THF (4 mL) and the mixture was stirred for 1 hour. The reaction mixture was quenched with a saturated aqueous NH4CI solution, diluted with brine and extracted with EtOAc. The organic layer was dried over magnesium sulphate, filtered and concentrated. The residue was purified by column (0775) chromatography using a gradient from 10 till 100% EtOAc in heptane. The obtained solid was dissolved in methanol (40 mL) and water was added untill crystallisation began. The product was filtered off and dried overnight in vacuo at 50C resulting in compound 164 (534 mg) as a white powder. Method D: Rt: 1.98 min. m/z: 511.1 (M-H)~ Exact mass: 512.0. DSC: From 30 to 300 C at 10C/min, peak 202.4 C. 1H NMR (400 MHz, ACETONITRILE-d3) delta ppm 1.85 – 1.93 (m, 2 H), 2.36 – 2.46 (m, 5 H), 2.47 – 2.57 (m, 2 H), 3.86 (s, 3 H), 6.48 (br. s, 1 H), 7.25 (d, J=4.8 Hz, 1 H), 7.42 (d, J=1.5 Hz, 1 H), 7.73 (d, J=1.5 Hz, 1 H), 8.47 (br. s, 1 H). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.79 – 1.91 (m, 2 H), 2.27 – 2.38 (m, 2 H), 2.39 – 2.49 (m, 5 H), 3.82 (s, 3 H), 7.52 (d, J=1.3 Hz, 1 H), 7.57 (d, J=4.4 Hz, 1 H), 7.77 (d, J=l . l Hz, 1 H), 8.73 (s, 1 H), 10.46 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,79055-59-7, 2-Bromo-6-methylpyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 79456-33-0, 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.79456-33-0, name is 5-Chloro-3-(trifluoromethyl)pyridin-2-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.

To a stirred solution of 5-chloro-3-(trifluoromethyl)pyridin-2-amine (Intermediate 47; CAS79456-33-0, 10 g, 50.9 mmol) in aqueous HBr (48 %, 56.7 g, 336 mmol) at -10 C wasadded bromine (23.6 g, 147.5 mmol) dropwise over 20 minutes, followed by a solution ofsodium nitrite (10.2 g, 147.8 mmol) in water (18 mL). The reaction was stirred at ambienttemperature for 2 hours and was basified (pH 9-10) and extracted into diethyl ether. Theorganic was washed with brine, dried (Na2504), filtered and concentrated in vacuo toafford the title compound without further purification.MS ES: 262

The chemical industry reduces the impact on the environment during synthesis 79456-33-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GOLDBY, Anne; JENKINS, Kerry; TEALL, Martin; WO2015/79224; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 197376-47-9, 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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate, molecular formula is C9H10ClNO2, 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 (E)-3-ethyl-1-(4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1, 3, 2] dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1-penten-3-ol (Example 39-(5); 50.0 mg, 0.10 mmol), (6-chloro-pyridin-3-yl)acetic acid ethyl ester (31.4 mg, 0.15 mmol), tetrakistriphenylphosphine palladium (16.9 mg, 0.0146 mmol) and potassium phosphate (33.4 mg, 0.15 mmol) in N,N-dimethylformamide (0.30 mL) was stirred with microwave heating at 140C for 10 minutes. The reaction mixture was filtered through cotton plug, and the residue was purified by silica gel chromatography (30 to 40% ethyl acetate/hexane) to give the title compound (37.6 mg, 69%). 1H-NMR (chloroform-d): 0.65 (t, 6H, J=7.3Hz), 0.92 (t, 6H, J=7.3Hz), 1.26 (t, 3H, J=7.1Hz), 1.64 (q, 4H, J=7.5Hz), 2.13 (q, 4H, J=7.2Hz), 2.30 (s, 3H), 3.64 (s, 2H), 4.18 (q, 2H, J=7.1Hz), 6.01 (d, 1H, J=16.1Hz), 6.75 (d, 1H, J=16.1Hz), 6.96-6.99 (m, 2H), 7.26-7.32 (m, 3H), 7.68 (s, 2H), 7.85 (d, 2H, J=8.4Hz), 8.56 (s, 1H).

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 197376-47-9, Ethyl 6-Chloropyridine-3-acetate.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1894911; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 7477-10-3 ,Some common heterocyclic compound, 7477-10-3, molecular formula is C6H3ClN2O4, 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.

Methyl 6-chloro-5-nitronicotinate was purchased from Sigma Aldrich or synthesized as follows. Toa solution of 6-chloro-5-nitronicotinic acid (Ark Pharm, Inc., 2.5 g, 12.3 mmol) in dry DMF (30mL) were added K2CO3 (2.5 g, 18.5 mmol) and iodomethane (8.76 g, 61.7 mmol). The solution wasstirred at room temperature for 24 h, then poured onto ice, and extracted with EtOAc (100 mL × 3).The organic layer was washed with H2O (100 mL × 2) and brine (100 mL), and dried over MgSO4.The solvent was evaporated under reduced pressure and the residue was purified by flash columnchromatography (EtOAc/n-hexane = 1/2) to afford 10 (2.4 g, 92percent) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7477-10-3, its application will become more common.

Reference:
Article; Takamura, Yuta; Takahashi, Manami; Nishii, Midori; Shibahara, Osamu; Watanabe, Masaki; Fujihara, Michiko; Kakuta, Hiroki; Bioorganic and Medicinal Chemistry Letters; vol. 29; 15; (2019); p. 1891 – 1894;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem