Category: pyridine-derivatives

Electric Literature of 153747-97-8, Adding some certain compound to certain chemical reactions, such as: 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate,molecular formula is C14H20BrN3O2, 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 153747-97-8.

[0951] A solution ofcompound 90b (125 g, 366 mmol) inDMF (1.30 L)was treatedwith, 4,4,4′,4′,5,5,5′,5′-octamethyl2,2′-bi(1,3,2-dioxaborolane) (186 g, 732 mmol), Pd(OAc) 2(4.09 g, 18.3 mmol), PPh3 (19.2 g, 73.2 mmol) and KOAc(108 g, 1.10 mol) under a nitrogen atmosphere. The resultingmixture was stirred overnight at 80 C. Upon cooling to roomtemperature, the solids were collected by filtration. The filtrate was concentratedunderreduced pressure, and the resultant residue was purified by flash colunm chromatography onsilica gel (EtOAc/petroleum ether (1 :50 v/v)) to obtain compound 90c as a white solid (80.0 g, 56% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C20H32BN3 0 4 : 390.2(M+H). found 390.2.

According to the analysis of related databases, 153747-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA, NV; Player, Mark R.; Meegalla, Sanath K.; Illig, Carl R.; Chen, Jinsheng; Wilson, Kenneth J.; Lee, Yu-Kai; Parks, Daniel J.; Huang, Hui; Patel, Sharmila; Lu, Tianbao; US2014/364414; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 884494-45-5, 2-Fluoro-4-iodo-6-methylpyridine, 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, 884494-45-5, blongs to pyridine-derivatives compound. COA of Formula: C6H5FIN

To a solution of 2-fluoro-4-iodo-6-methylpyridine (800 mg, 3.38 mmol, CAS 884494-45-5) and (S)-l,3-dihydrospiro[indene-2,4′-piperidin]-l-amine (1.11 g, 4.05 mmol, Intermediate I, 2HC1) in NMP (10.0 mL) was added DIPEA (2.35 mL, 13.50 mmol) at 25 C, then the mixture was stirred at 120 C for 24 h. Then, additional (S)-l,3- dihydrospiro[indene-2,4′-piperidin]-l-amine (464 mg, 1.69 mmol, Intermediate I, 2HC1) and DIPEA (1.18 mL, 6.75 mmol) were added with stirring at 120 C for 3 h. Next, (Boc)20 (1.10 g, 5.06 mmol, 1.16 mL) was added to the mixture with stirring, then the reaction was stirred at 25 C for 12 h. The reaction mixture was poured into water (100 mL), and then the aqueous phase was extracted with ethyl acetate (100 mL x 2). The combined organic phase was washed with brine (100 mL x 3), dried over Na2S04, filtered and concentrated in vacuo. The crude product was purified by column chromatography (100-200 mesh silica gel, petroleum ether/ethyl acetate=l00/l to 20/1, Product Rf = 0.48) to afford tert-butyl (S)-(l ‘-(4- iodo-6-methylpyridin-2-yl)-l,3-dihydrospiro[indene-2,4’-piperidin]-l-yl)carbamate (860 mg, 49% yield) as a yellow solid. LC-MS (ESI+) m/z 520.1 (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,884494-45-5, its application will become more common.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 63875-01-4, 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. 63875-01-4, name is 2-Methylisonicotinaldehyde. A new synthetic method of this compound is introduced below.

Example 38: Preparation of 4-Chloro-N-{5-chloro-2-fhvdroxy-(2-methyl-pyridin-4- yl)-methyl]-pyridin-3-yl)-N-methoxymethyl-3-trifluoromethyl benzenesulfonamide; [00427] To a stirred solution of N-(2-bromo-5-chloro-pyridin-3-yl)-4-chloro- N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (494 mg, 1.0 mmol) in anhydrous THF (10 mL) was added 2 M isopropylmagnesiumchloride in THF (1.20 mL, 2.4 mmol) at -40 °C. After 5 minutes dry ice-acetone bath was replaced with a ice water bath and stirred at 0 °C for 1 h. Solid 2-methyl-pyridine-4- carbaldehyde (327 mg, 2.7 mmol) was added in one portion and the progress of EPO the reaction was followed by LCMS. The reaction mixture was warmed to room temperature and stirred overnight. It was then quenched with saturated aqueous NH4CI (2 mL), and extracted with EtOAc. The combined extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to provide the desired product which was utilized in the following step without further purification. MS m/z: 536.0 (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,63875-01-4, its application will become more common.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
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.159783-22-9, name is 3,5-Difluoropyridin-4-amine, molecular formula is C5H4F2N2, molecular weight is 130.1, as common compound, the synthetic route is as follows.Recommanded Product: 159783-22-9

EXAMPLE 25 Compounds FQ-FR By proceeding as in Example 24 but using 4-amino-3,5-difluoropyridine instead of 4-amino-3,5-dichloropyridine, and using 3-cyclopentyloxy-4-(methylthio)benzoyl chloride and 4-(methylthio)-3-(tetrahydro-3-furyloxy)benzoyl chloride, there are prepared: N-(3,5-difluoropyrid-4-yl)-3-cyclopentyloxy-4-(methylthio)benzamide is synthesised; m.p. 174-5C. [Elemental analysis: C,59.4; H,5.1;; N,7.6; S,8.3%; calculated: C,59.3; H,5.0; N,7.7; S,8.3%]; and N-(3,5-difluoropyrid-4-yl)-4-(methylthio)-3-(tetrahydro-3-furyloxy)benzamide.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,159783-22-9, 3,5-Difluoropyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; RHONE-POULENC RORER LIMITED; EP741707; (1998); B1;,
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 94220-38-9, name is 7-Chloro-5-methyl-1H-pyrazolo[4,3-b]-pyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 94220-38-9

EXAMPLE 24 7-(3,4-Dichloroanilino)-5-methyl-1H-pyrazolo[4,3-b]pyridine (24) STR37 7-Chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine (1.5 g) and 3,4-dichloroaniline (1.45 g) were heated under reflux in ethanol (90 ml) for 48 h. The solvent was removed in vacuo to yield a yellow solid which was suspended in water and the pH adjusted to 7.8. The solid was filtered off, washed with water, and dried to yield the 7-(3,4-dichloroanilino)-compound (2.27 g, 87%) which was recrystallized from ethanol (charcoal) to yield a white amorphous solid m.p. 273 (dec.). (Found: C, 53.1; H, 3.5; N, 19.3; Cl, 24.1. C13 H10 N4 Cl2 requires C, 53.3; H, 3.45; N, 19.1; Cl, 24.2%), numax. 3400-2250 (N-H), 1630, 1580, 1530, 1410, 1400, 1310, 1135, 955, 850, 810 cm-1, delta (CF3 COOH) 2.76 (3H, s, 5-CH3), 6.86 (1H, s, 6-H), 7.49 (3H, m, aromatic protons), 8.46 (1H, s, 3-H), 9.47 (2H, s, N? H2), total proton count 10.

With the rapid development of chemical substances, we look forward to future research findings about 94220-38-9.

Reference:
Patent; Beecham Group, p.l.c.; US4559348; (1985); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 639091-75-1 ,Some common heterocyclic compound, 639091-75-1, molecular formula is C12H16N2O4, 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.

Compound 2E (2.5 g, 9.91 mmol, 1.00 equiv) and CaCl2 (1.65 g) were dissolved in EtOH (30 mL). The solution was cooled to 0C then NaBH4 (1.13 g, 29.87 mmol, 3.01 equiv) was gradually added. The solution was left under agitation overnight at ambient temperature then the reaction was halted with the addition of water (50 mL). The mixture was extracted three times with 20 mL of EtOAc. The organic phases were combined, washed twice with 20 mL of NaCl (sat.) then dried over sodium sulfate, filtered and concentrated under reduced pressure to yield 2.0 g (90 %) of compound 2F in the form of a colourless solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,639091-75-1, its application will become more common.

Reference:
Patent; PIERRE FABRE MEDICAMENT; GOETSCH, Liliane; JOUHANNEAUD, Alexandra; PEREZ, Michel; (129 pag.)WO2016/173682; (2016); A1;,
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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below., Safety of 5-Bromo-2-chloro-4-methoxypyridine

Step B: 6-Chloro-4-methoxypyridine-3-carbonitrile: A solution of 5-bromo-2-chloro-4- methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 min. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added successively. The resulting suspension was stirred at 95 C for 12 h under nitrogen. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product.

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, 880870-13-3, 5-Bromo-2-chloro-4-methoxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DONG, Shuzhi; PASTERNAK, Alexander; GU, Xin; FU, Qinghong; JIANG, Jinlong; DING, Fa-Xiang; TANG, Haifeng; DEJESUS, Reynalda, K.; SUZUKI, Takao; WO2015/100147; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59942-87-9, 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.59942-87-9, name is Pyrazolo[1,5-a]pyridin-2(1H)-one, molecular formula is C7H6N2O, molecular weight is 134.1353, as common compound, the synthetic route is as follows.

52a. Synthesis of 4,5,6,7-tetrahydropyrazolo[1 ,5-a]pyridin-2-ol A solution of pyrazolo[1 ,5-a]pyridin-2-ol (7.5 g, 0.056 mol) in 280 mL of AcOH was hydrogenated over 2.5 g of 10 wt % Pd/C dry powder for 20 h under atmospheric pressure of hydrogen. After 72 h, the suspension was filtered over decalite and concentrated under vacuum to afford an orange residue that was suspended in hot IPA and stirred for 15 min, then cooled to 0 5C and filtered to afford 4.84 g of a cream colored solid. The filtrate was concentrated under vacuum, and recrystallyzed from EtOAc to afford additional 2.62 g (global 96%). 1 H NMR (CDCI3) delta ppm: 5.32 (s, 1 H), 3.91 (t, J = 6.1 Hz, 2H), 2.69 (t, J = 6.3 Hz, 2H), 2.06 – 1 .91 (m, 2H), 1 .86 – 1 .69 (m, 2H).

Statistics shows that 59942-87-9 is playing an increasingly important role. we look forward to future research findings about Pyrazolo[1,5-a]pyridin-2(1H)-one.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE S.A.; DIAZ FERNANDEZ, Jose Luis; CUBERES ALTISENT, Mª Rosa; WO2013/124341; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69045-78-9 ,Some common heterocyclic compound, 69045-78-9, molecular formula is C6H3Cl4N, 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.

REFERENCE EXAMPLE 1 A reaction was conducted for 12 hours in the same manner as in Example 1 except that 2-chloro-5-trichloromethylpyridine (0.2 mole) was replaced by 3-trichloromethylpyridine (0.2 mole). The resulting reaction mixture was analyzed by gas chromatography, which indicated that the amount of 3-cyanopyridine formed was 1% or less.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69045-78-9, its application will become more common.

Reference:
Patent; Ihara Chemical Industry Co., Ltd.; US5675012; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 90145-48-5, 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 90145-48-5, name is 5-Bromopyridine-2-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1-1-isopropyl-3-methyl-1H-pyrazol-4-yf)-3-methyl-8-(4,4 5,5-tetramethyl- (1 ,3,2]dioxaborolan-2-yl)-1,3-d.hydroimidazo[4,5-c]quinolin-2-one (Stage 112.1.1 , 34 mg, 0.075 mmol), delta-bromo-py?dine^-carboxylic acid amide (Combi-Blocks, San Diego, USA, 20 mg, 0 099 mmol), and PdCI2(PPh3)2 (3.5 mg, O 005 mmol) in DMF (O 9 ml) and 1 M aqueous K2CO3 (0.187 ml) was stirred under argon at 105 C for 2.5 h The RM was cooled to rt. The mixture was diluted with MeOH + 3 drops TFA and purified directly by Prep.HPLC (H2O (0.1% TFA)/CH3CN 97:3 to 55:45). The fractions containing product were collected together and basifted with NaHCO3 (0.3 g), before being concentrated The resulting layer was extracted with DCM, washed with brine, dned over Na2SO4, filtered and evaporated to dryness to give the title compound as a white solid (HPLC: tR 2.44 mm (Method A): M+H ~ 442 MS-ES; 1H-NMR (dbeta-DMSO, 400 MHz) 9.00 (s, 1H). 8 75-8 69 (m, 1H), 8.24-8.19 (m, 1H), 8.18-8.07 (m, 2H) 8.07-7.98 (m, 3H), 7.75-7.67 (m, 1 H), 7 61-7.56 (m, 1H)1 4.61-4 48 (m, 1H). 3.58 (s, 3H), 1 97 (s, 3H), 1.45 (s, 3H), 1.43 (s, 3H)).

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 90145-48-5, 5-Bromopyridine-2-carboxamide.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; KALTHOFF, Frank Stephan; MAH, Robert; RAGOT, Christian; STAUFFER, Frederic; WO2010/139731; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem