Category: pyridine-derivatives

Reference of 824-51-1, 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 824-51-1, name is 6-Methyl-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

PREPARATION 131 1 -(2-((1 ,4-Dimethyl-1 H-pyrazol-5-yl)methyl)-4-fluorophenyl)-6-methyl-1 H- pyrrolo[2,3-b]pyridine The title compound of Preparation 58 (0.150 g, 1 .13 mmol), potassium phosphate (0.48 g, 2.27 mmol) and the title compound of Preparation 130 (0.337 g, 1 .19 mmol) were suspended in 3 ml 1 ,4-dioxane in a Schlenk vessel and the mixture was subjected to three vacuum-argon cycles. Copper(l) iodide (44 mg, 0.23 mmol) and trans-N1 ,N2-dimethylcyclohexane-1 ,2-diamine (0.072 ml, 0.46 mmol) were added and the mixture was submitted to three further vacuum-argon cycles. The reaction vessel was sealed and the mixture was stirred at 130 C for 72 h. Further copper(l) iodide (22 mg, 0.12 mmol) and trans-N1 ,N2-dimethylcyclohexane-1 ,2-diamine (0.036 ml, 0.23 mmol) were added and the kixture was stirred at 130 C for 48 h. The mixture was allowed to cool to room temperature, diluted with ethyl acetate and filtered through Celite. The filtrate was evaporated under reduced pressure and the residue was purified by reverse-phase chromatography using the Isolera Purification System to give 140 mg (0.42 mmol, 37%) of the title compound as an oil. Purity 98%. 1 H N MR (300 MHz, CHLOROFORM-d) delta ppm 7.88 (d, 1 H, J = 8.2 Hz), 7.28-7.33 (m, 2H), 7.16 (d, 1 H, J = 3.5 Hz), 7.01 -7.08 (m, 2H), 6.61 (d, 1 H, J = 3.5 Hz), 6.56 (dd, 1 H, J = 9.4, 2.9 Hz), 3.76 (br s, 2H), 3.58 (s, 3H), 2.58 (s, 3H), 1 .90 (s, 3H). UPLC/MS (3 min) retention time 1 .87 min. LRMS: m/z 335 (M+1 ).

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 824-51-1, 6-Methyl-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; ALMIRALL, S.A.; VIDAL JUAN, Bernat; ALONSO DIEZ, Juan Antonio; BUIL ALBERO, Maria Antonia; EASTWOOD, Paul Robert; ESTEVE TRIAS, Cristina; LOZOYA TORIBIO, Maria Estrella; ROBERTS, Richard Spurring; VIDAL GISPERT, Laura; GONZALEZ RODRIGUEZ, Jacob; MIR CEPEDA, Marta; WO2013/10880; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 915720-71-7, Adding some certain compound to certain chemical reactions, such as: 915720-71-7, name is (S)-tert-Butyl (1-(5-bromopyridin-2-yl)ethyl)carbamate,molecular formula is C12H17BrN2O2, 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 915720-71-7.

Intermediate 67: (5)-tert-butyl (1 -(5-(4-fl uoro-3-methylphenyl)pyridin-2-yI)ethyl)carbamate In a 5 mL microwave vial a solution of (5)-tert-butyl (1-(5-bromopyridin-2-yl)ethyl)carbamate(60 mg, 0.2 mmol), (4-fluoro-3-methylphenyl)boronic acid (37 mg, 0.24 mmol), Sodiumbicarbonate (0.2 mL, 0.4 mmol, 2 M aqueous solution) in Dioxane (2 mL) was bubbled N2 for 3mm then CI2Pd(dppf)CH2CI2 (16 mg, 0.02 mmol) was added. The capped tube was heated to100C for 16 h. After cooling the reaction mixture was diluted with EtOAc (10 mL) and washedwith water (10 mL). After separation, the aqueous phase was extracted with EtOAc (3 x 10 mL). Combined organics were dried over Na2504, filtered and concentrated. The crude material was purified through silica gel column chromatography (EtOAc in Heptane 12 to 100%) to give a white solid (66 mg, 80% yield). LCMS tR = 1.43 mm; MS m/z 331.1 (M+H).

According to the analysis of related databases, 915720-71-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; CHO, Young Shin; LEVELL, Julian Roy; LIU, Gang; SHULTZ, Michael David; VAN DER PLAS, Simon Cornelis; WO2014/141153; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13269-19-7 ,Some common heterocyclic compound, 13269-19-7, molecular formula is C5H5N3O2, 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 stirred suspension of 2-nitro-pyridin-3-ylamine (5.06 g, 36.40 mmol) and sodium acetate (2.99 g, 36.46 mmol) in acetic acid (40 mL), a solution of bromine (2.5 mL, 48.79 mmol) in acetic acid (8 ml) was added drop-wise and the reaction mixture was stirred overnight. The acetic acid was removed under reduced pressure. The residue was cooled toO0C, neutralized with saturated sodium bicarbonate solution to adjust the pH to ~7, and extracted with ethyl acetate (4 x 50 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was triturated with ethyl acetate to afford compound (5) (5.1 g) as a yellow solid.1H NMR (DMSO-de, 400MHz) delta: 7.66 (d, J=8.6 Hz, 1 H), 7.58 (s, 2 H), 7.49 (d, J=8.6 Hz,I H)ESMS: m/z 216.33 [M-I]”

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. 13269-19-7, 2-Nitropyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; BJOeRK, Seth; DELISSER, Vern; JOHNSTROeM, Peter; NILSSON, Nils Anders; RUDA, Katinka; SCHOU, Per Magnus; SWAHN, Britt-Marie; WO2010/24769; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52378-63-9, (3-Aminopyridin-2-yl)methanol, 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, Quality Control of (3-Aminopyridin-2-yl)methanol, blongs to pyridine-derivatives compound. Quality Control of (3-Aminopyridin-2-yl)methanol

ii. A solution of sodium nitrite (2.38 g) in water (10 ml) was added dropwise to a mixture of 3-amino-2-hydroxymethylpyridine (4.8 g), aqueous hydrochloric acid (48%, 10 ml) and water (5 ml) stirred at 0 – 5. This solution was added to a hot solution of cuprous chloride (2.5 g) in conc. hydrochloric acid and the mixture was heated on a steam-bath for 0.5 hours, diluted with water and saturated with hydrogen sulphide. The mixture was filtered, concentrated and extracted with chloroform and the chloroform extract was evaporated to give 3-chloro-2-hydroxymethylpyridine (3.7 g) m.p. 42- 44 (from n-pentane).

The synthetic route of 52378-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4056621; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 639091-75-1, 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 639091-75-1, name is Methyl 2-(Boc-amino)isonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

A slurry of methyl 2-((tert-butoxycarbonyl)amino)isonicotinate (50.4 g, 200 mmol) in DMF (500 mL) was cooled to 0C and sodium hydride (10.4 g, 60% in mineral oil, 260 mmol) was added portion wise. The mixture was allowed to warm to RT and stirred for 30 min. To the reaction iodomethane (37.2 g, 262 mmol) was slowly added. The resulting mixture was stirred at RT overnight. The reaction was quenched by addition of aqueous ammonium chloride (100 mL) and diluted with water (400 mL). The mixture was extracted with EA (250 mL x 2). The combined organic phase was washed with water (100 mL) and brine (100 mL), dried over MgSO4 and concentrated. The residue was chromatographed, eluting with 5:1 hexane:EA) to give the product as colorless oil (48.9 g, 92%).1H NMR (400 MHz, CDCl3) delta 1.54 (s, 9H), 3.42 (s, 3H), 3.94 (s, 3H), 7.52 (d, 1H), 8.27 (s, 1H), 8.48 (d, 1H).

According to the analysis of related databases, 639091-75-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXITHERA PHARMACEUTICALS, INC.; CHENARD, Bertrand, L.; XU, Yuelian; STASSEN, Frans, L.; HAYWARD, Neil, J.; (225 pag.)WO2018/118705; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 194673-12-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 194673-12-6 as follows.

A solution of 6-hydroxy-2-trifluoromethyl-4,5-dihydro-pyridine-3-carboxylic acid ethyl ester (Description 16) (4.7 g, 19.8 mmol, 1 eq) and N-bromosuccinimide (3.51 g, 19.8 mmol, 1 eq) in 15 ml of carbon tetrachloride was heated under reflux for 20 h. The resulting precipitate was filtered off and the filtrate was concentrated under reduced pressure to afford a brownish solid that was purified by flash chromatography (silica gel, eluent gradient: from hexane/ethyl acetate 9:1 to hexane/ethyl acetate 8:2). The title compound was obtained as a white solid (4.3 g, yield = 92%). LC-MS (ESI+), MH+: 236

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,194673-12-6, its application will become more common.

Reference:
Patent; Glaxo Group Limited, Glaxo Group Limited; WO2004/29027; (2004); 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.72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.Quality Control of 2-Chloro-5-(trifluoromethyl)pyridin-3-amine

A 100-mL round bottom flask equipped with a magnetic stirrer was charged with 2-chloro-5-(trifluoromethyl)pyridine-3-amine (1.0 g, 5.1 mmol), CH2Cl2 (15 mL), TEA (1.42 ml, 10.2 mmol). The reaction mixture was cooled under ice-bath and chloroacetyl chloride (0.81 ml, 10.2 mmol) was slowly added. The reaction mixture was stirred at room temperature for 2 hours. The solvent was removed under vacuum. The residue was purified by column chromatography using 20% EtOAc/hexane to afford the desired product as off-white solid (1.22 g, 88% yield).). 1H NMR (300 MHz, CDCl3) delta: 9.05 (s, 2H), 8.44 (s, 1H), 4.27 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; LaVoie, Edmond J.; Parhi, Ajit; Pilch, Daniel S.; Zhang, Yongzheng; Kaul, Malvika; US2015/133465; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 619331-71-4 ,Some common heterocyclic compound, 619331-71-4, molecular formula is C7H4Br2N2, 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 mixture of 2u (2.0 g, 7.3 mmol) and CuCN (1.0 g, 11 mmol) was added DMF (20 ml). The reaction mixture was heated at 150 C. for 1 hour. After cooling to room temperature, the reaction mixture was added NaOMe (20 ml, 25 wt. % solution in MeOH), and was heated at 110 C. for 10 minutes. After cooling to room temperature, the reaction mixture was poured into an aqueous solution of ammonium acetate (sat. 500 ml). The resulting mixture was filtered through a short Celite pad. The filtrate was extracted with EtOAc (500 ml×4). The combined extracts were dried over MgSO4 and evaporated in vacuo to give a brownish residue, which was triturated with MeOH (5 ml×3) to provide precursor 2v as a yellow solid (317 mg, 25%). The structure was supported by NOE experiments. 1H NMR: (DMSO-d6) 12.47 (s, 1H), 8.03 (s, 1H), 7.65 (t, J=2.8, 1H), 6.70 (dd, J=2.8, 1.8, 1H), 4.08 (s, 3H); LC/MS: (ES+) m/z (M+H)+=174; HPLC (alternate conditions B, column G) Rt=1.320.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,619331-71-4, its application will become more common.

Reference:
Patent; Wang, Tao; Zhang, Zhongxing; Meanwell, Nicholas A.; Kadow, John F.; Yin, Zhiwei; Xue, Qiufen May; Regueiro-Ren, Alicia; Matiskella, John D.; Ueda, Yasutsugu; US2004/110785; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 928653-73-0 ,Some common heterocyclic compound, 928653-73-0, molecular formula is C5H2BrClIN, 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 1 : Sodium hydride (2.0 equiv.) was added to dioxane (0.3 M). 2- ((tetrahydro-2H-pyran-2-yl)oxy)ethanol (2.0 equiv.) was added and the mixture was stirred for 30 min at rt. 5-bromo-2-chloro-3-iodopyridine (1.0 equiv.) was added to the mixture and the reaction was heated to 105 C for 1 hour. The cooled reaction mixture was quenched by the addition of saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography over silica gel (heptanes with 10% ethyl acetate) to give 5-bromo-3-iodo-2-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy )pyridine as a colorless oil in 78% yield. LCMS (m/z) (M+H) = 427.8/429.8, Rt = 1.12 min.

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. 928653-73-0, 5-Bromo-2-chloro-3-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; AVERSA, Robert John; BURGER, Matthew T.; DILLON, Michael Patrick; DINEEN JR., Thomas A.; LOU, Yan; NISHIGUCHI, Gisele A; RAMURTHY, Savithri; RICO, Alice C.; RAUNIYAR, Vivek; SENDZIK, Martin; SUBRAMANIAN, Sharadha; SETTI, Lina Quattrocchio; TAFT, Benjamin R.; TANNER, Huw Rowland; WAN, Lifeng; (307 pag.)WO2016/38582; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1256561-65-5 ,Some common heterocyclic compound, 1256561-65-5, molecular formula is C6H6Br2FN, 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.

Potassium carbonate (193 mg, 1.396 mmol) and 3-(bromomethyl)-5-fluoropyridine hydrobromide (151 mg, 0.558 mmol; Sunshine Chemlab) were added to a solution of 2.2.7-trifluoro-8-(1-hydroxyethyl)-2H-1 ,4-benzoxazin-3(4H)-one (138 mg; may be prepared as described in intermediate 1 1 ) in dry DMF (5 ml_). The mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was dissolved in DCM (3 ml.) and 10% w/v aqueous citric acid (2 ml_). The layers were separated and the aqueous was extracted with DCM (2 x 2 ml_). The combined organic layers were dried (hydrophobic frit) and evaporated to give a brown oil (137 mg). This was purified by MDAP (formic acid method) to give a brown oil (104 mg). 96 mg of this racemic mixture was resolved using a Chiralpak AS column eluting with heptane: ethanol (90:10) v/v pump-mixed. Using these conditions the faster-running enantiomer 2,2,7-trifluoro-4-[(5- fluoro-3-pyridinyl)methyl]-8-[(1 S)- 1 -hydroxyethyl]-2H-1 ,4-benzoxazin-3(4H)-one (42 mg, Compound 99) and the slower-running enantiomer 2,2,7-trifluoro-4-[(5-fluoro-3- pyridinyl)methyl]-8-[(1 R)-1-hydroxyethyl]-2H-1 ,4-benzoxazin-3(4H)-one (40 mg, Compound 100) were obtained in >99% enantiomeric excess. 1H NMR (CD3OD) delta: 1.60 (3H, d), 5.32 – 5.40 (1 H, m), 7.01 (1 H, t), 7.18 – 7.25 (1 H, m), 7.57 (1 H, d), 8.38 – 8.45 (2H, m). m/z [M+H]+: 356.9 Retention time 0.85 min (LC/MS method 3). The absolute configurations were determined by ab initio vibrational circular dichroism.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1256561-65-5, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/12622; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem