Category: pyridine-derivatives

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. 73112-16-0, name is 2,6-Dibromo-4-methylpyridine, molecular formula is C6H5Br2N, 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. Safety of 2,6-Dibromo-4-methylpyridine

Step 1: Synthesis of (lS,4S)-ethyl 4-(6-bromo-4-methylpyridin-2-yl)-4-hydroxycyclohexane- carboxylate and (lR,4R)-ethyl 4-(6-bromo-4-methylpyridin-2-yl)-4-hydroxycyclohexane- carboxylate. (0253) (0254) (less polar by TLC) (more polar by TLC) (0255) A solution of 2,6-dibromo-4-methylpyridine (1.00 g, 3.98 mmol) in DCM (30 mL) was cooled to -78 C, and n-BuLi (2.5 M, 1.74 mL, 4.37 mmol) was added dropwise to the above solution at -78 C. The solution was stirred at -78 C for 15 minutes, followed by addition of ethyl 4-oxocyclohexanecarboxylate (811 mg, 4.77 mmol), and the resultant mixture was stirred at -78 C for 30 min. The mixture was then quenched by addition of saturated aqueous NH4C1 solution and extracted with DCM. Organic layers were combined, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel column (PE:EA = 2: 1) to give (lR,4R)-ethyl 4-(6-bromo-4-methylpyridin-2-yl)-4-hydroxycyclohexanecarboxylate (less polar by TLC, 500 mg, 36.7%) as a white solid, MS (ES+) Ci5H2oBrN03 requires: 341, found: 342 [M+H]+, and (lS,4S)-ethyl 4-(6-bromo-4-methylpyridin-2-yl)-4-hydroxycyclohexanecarboxylate (more polar by TLC, 500 mg, 36.7%) as a white solid. MS (ES+) Ci5H20BrNO3 requires: 341, found: 342 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 73112-16-0.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; KIM, Joseph, L.; WILSON, Kevin, J.; WILSON, Douglas; DIPIETRO, Lucian, V.; (84 pag.)WO2017/79140; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 785762-99-4 ,Some common heterocyclic compound, 785762-99-4, molecular formula is C8H6F3NO2, 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.

(3) To a 250 ml single-mouth bottle, 3.5 g (0.094 mol, 1.0 eq) of sodium hydroxide and 18 ml of water (1 v/w) were added, and the mixture was stirred and dissolved. compound 785762-99-4 18 g (0.094 mol, 1.0 eq) was added to the system and the mixture was dissolved. After stirring at 25 C for 0.5 h, the reaction solution was concentrated. A pale yellow solid powder was obtained in a yield of 90.7%. The nuclear magnetic data is as follows:

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. 785762-99-4, 2-(5-(Trifluoromethyl)pyridin-2-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Chen Min; (6 pag.)CN108997202; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 139585-48-1, 2-Chloro-5-methoxypyridine, 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, Recommanded Product: 2-Chloro-5-methoxypyridine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Chloro-5-methoxypyridine

(Step 6) Preparation of 8-(6-tert-butyl-1H-benzo[d]imidazol-2-yl)-4-(5-methoxypyridin-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine [117] To a solution of 4-(5-tert-butyl-1H-benzo[d]imidazol-2-yl)benzene amine 3.1 g (10 mmol) in toluene 10 mL were added 2-chloro-5-methoxy pyridine 1.5 g (10 mmol), Pd(OAc)2 0.1 g (0.5 mmol) and 2,2?-bis(diphenylphosphino)-1,1?-binaphthyl 0.5 g (0.8 mmol) and Cs2CO3 4.6 g (14 mmol), followed by stirring at 90C for 12 hrs. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and diluted with ethylacetate. The product thus formed was washed with a saturated sodium bicarbonate solution and a saturated NaCl solution, dried over magnesium sulfate and concentrated in a vacuum. The residue was purified by column chromatography (developing solvent: ethylacetate/hexane=2/3) to give 3.5 g of the title compound (yield 85%).[118] 1H NMR(MeOD-d4) delta : 8.04(d,1H, J=3.0Hz), 7.79(dd, 2H, J=7.8, 1.5Hz), 7.67(d, 1H, J=1.7Hz), 7.56(d, 1H, J=8.6Hz), 7.38(m, 2H), 7.25(d, 1H, J=9.0Hz), 7.17(dd, 1H, J=8.1, 1.4Hz), 6.95(t, 1H, J=8.0Hz), 4.52(t, 2H, J=4.4Hz), 3.99(t, 2H, J=4.4Hz), 3.86(s, 3H), 1.41 (s, 9H)

The synthetic route of 139585-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAEWOONG PHARMACEUTICAL CO., LTD.; KIM, Ji Duck; YOON, Hong Chul; KIM, In Woo; CHO, Min Jae; LEE, In Young; LEE, Sang Ho; PARK, Eun Kyung; LIM, Kwon Jo; NAM, Sang Hyun; WO2012/50380; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 75806-86-9, 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. 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine. A new synthetic method of this compound is introduced below.

A dry 250 mL flask was charged with 2-bromo-5-chloro- 3-niotatropyriotadiotane (24 g, 101 mmol), CuCN (19 g, 212 mmol) and DMF (100 mL) The resultant mixture was stirred at 1 10 0C for 2 hours The mixture was concentrated under reduced pressure Water (100 mL) was added and extracted with EtOAc (3 X 250 mL) The combined organic layer was washed with brine, dried (MgSO4) and filtered The solvent was evaporated the solvent in vacuo to afford a light yellow solid (15 g) which was used directly for the next step

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75806-86-9, 2-Bromo-5-chloro-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2009/9740; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 490-11-9, 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.490-11-9, name is Pyridine-3,4-dicarboxylicacid, molecular formula is C7H5NO4, molecular weight is 167.12, as common compound, the synthetic route is as follows.

Pyridine-3,4-dicarboxylic acid (40g, 0.24mmol) was added to SOCl2 (400mL) and heated to reflux for 80 deg C fo 3h. the solvent was distilled off under reduced pressure, at 0 added dropwise to methanol (200 mL), and stirred for half an hour at room temperature, the solvent was distilled off under reduced pressure, the solid was dissolved with ethyl acetate (a 500 mL), washed twice with saturated NaHCO3 solution, the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound (41g, yield 87.8 %)

Statistics shows that 490-11-9 is playing an increasingly important role. we look forward to future research findings about Pyridine-3,4-dicarboxylicacid.

Reference:
Patent; Shandong Xuan Bamboo Pharmaceutical Technology Co., Ltd.; Wu, Yong qian; (49 pag.)CN105461714; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1175512-08-9, name is Methyl 5-bromo-4-hydroxynicotinate, molecular formula is C7H6BrNO3, 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. Formula: C7H6BrNO3

Step 1: Methyl 5-bromo-1-isopropyl-4-oxo-1,4-dihydropyridine-3-carboxylate A mixture of methyl 5-bromo-4-oxo-1,4-dihydropyridine-3-carboxylate (151 mg, 0.65 mmol) and Cs2CO3 (420 mg, 1.3 mmol) in DMF (3 mL) was stirred at rt for 15 min and then isopropyl iodide (0.16 mL, 1.6 mmol) was added. The reaction mixture was stirred at rt for 11 days, diluted with EtOAc, filtered through Celite concentrated, and purified via column chromatography (0% to 100% EtOAc in hexanes then 0% to 10% methanol in CH2Cl2) to give the product as an off-white solid (103 mg, 58%). LCMS calcd for C10H13BrNO3 (M+H)+: m/z=274.0. Found: 274.1.

With the rapid development of chemical substances, we look forward to future research findings about 1175512-08-9.

Reference:
Patent; Incyte Corporation; Li, Yun-Long; Wang, Xiaozhao; Barbosa, Joseph; Burns, David M.; Feng, Hao; Glenn, Joseph; He, Chunhong; Huang, Taisheng; Mei, Song; Zhuo, Jincong; (169 pag.)US2017/275290; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6318-51-0, (4-Chlorophenyl)(pyridin-2-yl)methanone, 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, 6318-51-0, blongs to pyridine-derivatives compound. Recommanded Product: (4-Chlorophenyl)(pyridin-2-yl)methanone

10L glass reactor with mechanical stirring,thermometer,Under nitrogen protection,First with magnesium shavings,p-chlorobenzaldehyde and tetrahydrofuran heated to form a solution,And then dropping 2-cyanopyridine,The reaction to the remaining 2-cyanopyridine remaining,Cooling for post-processing,Add water quench,Adjust pH to about 5,The organic phase was separated and the reaction product was extracted with ethyl acetate,The solvent was concentrated by petroleum ether to obtain the crude product of the first step. The crude product was purified by petroleum ether and ethyl acetate. First add the first step product and 95% ethanol,Add sodium borohydride cooling,The reaction to no raw material for post-treatment,The system is concentrated to dryness,Add water and stir,Suction filtered crude,After ethyl acetate and activated carbon decolorization,Purification with petroleum ether and ethyl acetate gave the pure product of alpha- (4-chlorophenyl) pyridine-2-methanol,The total molar yield was 75% with a purity of 99.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6318-51-0, its application will become more common.

Reference:
Patent; Bengbu Zhong Shi Chemical Co., Ltd.; Yang Qing; Zhao Shimin; Xu Jianxiao; Sun Jiale; (5 pag.)CN106946767; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 62002-31-7, 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. 62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride. A new synthetic method of this compound is introduced below.

To a mixture of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine dihydrochloride (0.50 g, 2.55 mmol), ethanol (10 mL) and triethylamine (1.10 mL, 7.89 mmol), 2,4-dichlorobenzyl isocyanate (0.52 g, 2.57 mmol) was added. The resulting mixture was stirred at room temperature for 16 h and then concentrated under reduced pressure. The residue was distributed between water (20 mL) and ethyl acetate (75 mL). The organic phase was washed with water (10 mL) and brine (10 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was triturated in diethylether (50 mL) and the crude product was filtered off. Recrystallization from acetone (25 mL) gave 0.30 g (37%) of the title ureaurea as a colourless solid. HPLC (214 nm): elution at 7.97 min. LC-MS: Calcd. for MH+: 325; found: 325. 1H NMR (400 MHz, DMSO-d6): delta2.56 (s, br, 2H), 3.65 (t, J=6 Hz, 2H), 4.29 (d, J=6 Hz, 2H), 4.34 (s, 2H), 7.20 (s, br, 1H), 7.29 (d, J=8 Hz, 1H), 7.39 (dd, J=8, 1 Hz, 1H), 7.47 (s, 1H), 7.56 (d, J=1 Hz, 1H), 11.79 (s, br, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62002-31-7, its application will become more common.

Reference:
Patent; Novo Nordisk A/S; US6908926; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, 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. HPLC of Formula: C6H4ClF3N2

The preparation of 3-amino-2,6-dichloro-5-trifluoromethyl-pyridine from 3-amino-2- chloro-5-trifluoromethyl-pyridine was as follows. A solution of 3-amino-2-chloro-5- trifluoromethyl-pyridine (5 g) (prepared as described in EP 178260, EP 272824) and N- chlorosuccinimide (3.7 g) in acetonitrile (125 ml) was stirred at ambient temperature for 16 hours. The reaction mixture was poured into water, extracted with ethyl acetate, dried over sodium sulfate and then concentrated in vacuo. Chromatography on silica gel (eluent: hexane / ethyl acetate 3:1) afforded 3-amino-2,6-dichloro-5-trifluoromethyl-pyridine (3.5 g): MS (ES+) 231 / 233 / 235 (MH+); IH NMR (400 MHz, CDCl3) 4.34 (s, 2H), 7.35 (s, IH).

With the rapid development of chemical substances, we look forward to future research findings about 72587-18-9.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2009/138219; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 846036-96-2, 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. 846036-96-2, name is (4-Amino-6-chloropyridin-3-yl)methanol. A new synthetic method of this compound is introduced below.

To a solution of (4-amino-6-chloro-pyridin-3-yl)-methanol (0.335 g, 2.1 mmol) (from Example 23 supra) in dichloromethane (100 mL) at room temperature was added MnO2 (1.9 g, 21.8 mmol). The reaction mixture was stirred at this temperature for 16 hours then filtered. Solvent was evaporated to give 4-amino-6-chloro-pyridine-3-carbaldehyde as a white solid which was used directly in the next step. (Yield 0.275 g, 83.9%). 1H NMR (300 MHz, CDCl3): delta 9.90 (s, 1H), 8.38 (s, 1H), 6.58 (s, 1H), 1.57 (s, 2H). LC-MS: [M+H]+ 157.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,846036-96-2, (4-Amino-6-chloropyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Luk, Kin-Chun; US2012/184562; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem