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. 630395-95-8, name is 1H-Pyrrolo[3,2-c]pyridine-2-carbaldehyde, molecular formula is C8H6N2O, 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. COA of Formula: C8H6N2O

1H-Pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl ester, 5b-1 (Scheme 3, step j) Add to a 0 C. solution of 1H-pyrrolo[3,2-c]pyridine-2-carboxaldehyde (9b-1, 3.24 g, 22.19 mmol) in methanol under argon, sodium cyanide (5.44 g, 111 mmol) and manganese dioxide (9.65 g, 111 mmol). Stir the reaction mixture for 5 h, filter through Celite and dilute with 500 ml EtOAc. Wash the organic layer with water (2*) and brine, dry over sodium carbonate, filter, and concentrate to provide the title compound (3.27 g) as a pure tan solid.

With the rapid development of chemical substances, we look forward to future research findings about 630395-95-8.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US2005/131012; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 637348-81-3, Adding some certain compound to certain chemical reactions, such as: 637348-81-3, name is 3-Bromo-5-iodopyridin-2-ol,molecular formula is C5H3BrINO, 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 637348-81-3.

Example 142b 3-Bromo-5-iodo-1-methylpyridin-2(1H)-one 142b A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with DMF (50 mL), 142a (6.0 g, 20.0 mmol), CH3I (4.26 g, 30.0 mmol), and K2CO3 (5.52 g, 40.0 mmol). The mixture was stirred at room temperature for 2 h and diluted with water (200 mL). The resulting white solid was collected by filtration to afford 142b (5.97 g, 95%) as a white solid. MS-ESI: [M+H]+ 314

According to the analysis of related databases, 637348-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); 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. 94170-15-7, name is 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde. A new synthetic method of this compound is introduced below., Computed Properties of C7H7NO2

2-((3S,4S)-4-(cyclopropylmethyl)pyrrolidin-3-yl)-7-(1,1-dioxothiomorpholino)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (129.98 mg)Dissolved in DCM (6 mL),Add 4-aldehyde-1-methylpyridine-2(1H)-one (54.6 mg, 0.398 mmol)Sodium triacetoxyborohydride (254.3 mg, 1.2 mmol) was stirred at room temperature overnight.TLC monitors the reaction completely,Add saturated aqueous sodium bicarbonate (5 mL),Extracted with DCM (3 x 10 mL),Combine the organic phase,Washed (2 × 5mL),Dry over anhydrous sodium sulfate,filter,concentrate,The crude product was subjected to silica gel column chromatography (DCM:MeOH=100:1-20:1)Purification of the white solid 2-((3S,4S)-4-(cyclopropylmethyl)-1-((1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-Pyrrolidin-3-yl)-7-(1,1-dioxothiomorpholinyl)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one(39.5 mg, yield: 23.2%).

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, 94170-15-7, 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Wang Lin; Yang Xiaoju; Tian Yuwei; (46 pag.)CN108341819; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 69045-83-6, 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 69045-83-6 as follows.

2, 3-dichloro-5-trichloromethylpyridine (36.60 g, 0.139 mol) was added to a flask containing acetic acid (53.50 g, 0.892 mol) and methanol (200 mL). The mixture was cooled to-5 C, and zinc dust (20.01 g, 0.308 mol) was added in small portions at 10 minute intervals. The mixture was stirred mechanically for 4 hours, filtered, and concentrated in vacuo. The residue was dissolved in dichloromethane and washed with brine, followed by saturated aqueous sodium bicarbonate, followed by a second brine wash. The organic phase was dried over magnesium sulfate and concentrated in vacuo to yield 21.55 g (79%) of Preparatory Compound P, 2, 3-DICHLORO-5- (CHLOROMETHYL) pyridine, as a yellow liquid (about 65% PURITY). 1H NMR No. 8.31 (d, 1H, J=2.3 Hz), 7.85 (q, 1H, J=0.4 Hz and J=2.2 Hz), 4.56 (s, 2H). MS (ESI) NIZ 199 ([M+4] +, 8), 197 ([M+2]+, 27), 195 ([M]+, 28), 164 (11), 162 (66), 160 (100), 124 (19)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69045-83-6, its application will become more common.

Reference:
Patent; DOW AGROSCIENCES LLC; WO2004/57960; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 866775-18-0, Adding some certain compound to certain chemical reactions, such as: 866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate,molecular formula is C8H6BrF3N2O2, 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 866775-18-0.

3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (1.40 g, 4.68 mmol) was suspended in MeOH (15 ml); Sodium hydroxide (2.0 M aqueous solution) (14.04 ml, 28.1 mmol) was added and the suspension was stirred at RT overnight. The reaction mixture was concentrated in vacuo and the resulting residue was dissolved in water (100 ml) and then acidifed by the addition of 5.0M HCI(aq). The product was extracted into ethyl acetate (2 x 75 ml) and the combined organic extracts were washed with water (50 ml), brine (25 ml), dried (MgS04) and concentrated in vacuo to afford the title product as a yellow solid. 1H-NMR: [400MHz, DMSO-de, deltaEta 13.24 (1 H, br s, C02H), 7.74 (1 H, s, ArH), 7.17 92H, br s ArNH2). m/z 285.1 , 287.1 [M+H]+

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. 866775-18-0, Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BALA, Kamlesh, Jagdis; BUDD, Emma; EDWARDS, Lee; HOWSHAM, Catherine; LEGRAND, Darren, Mark; TAYLOR, Roger, John; WO2013/38390; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58236-70-7, 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 58236-70-7 as follows.

Step2: 5-Bromo-3-chloro-2-((tetrahydro-2H-pyran-4-yl)oxy)pyridine[254][255]Potassium carbonate (2.0 eq.) was added to a solution of tetrahydro-2H-pyran-4-yl methanesulfonate (1.2 eq.) and 5-bromo-3-chloropyridine-1-ol (1.0 eq.) in N,N-dimethylformamide (0.2 M). The reaction mixture was stirred at 100 for 18 h. The reaction mixture was allowed to reach room temperature, diluted with ethyl acetate and washed with water. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated. The resultant residue was purified by flash column chromatography on silica gel to afford 5-bromo-3-chloro-2-((tetrahydro-2H-pyran-4-yl) oxy) pyridine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58236-70-7, its application will become more common.

Reference:
Patent; IL DONG PHARMACEUTICAL CO., LTD.; KANG, Jae-Hoon; LEE, Hong-Sub; AN, Kyung-Mi; HONG, Chang-Hee; KWAK, Hyun-Jung; CUI, Shuo-Lin; SONG, Hyo-Jung; (55 pag.)WO2018/111012; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1186637-43-3, 3-Bromo-6-methoxypicolinonitrile, 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-Bromo-6-methoxypicolinonitrile, blongs to pyridine-derivatives compound. Quality Control of 3-Bromo-6-methoxypicolinonitrile

A solution of 2-(te/i-butoxycarbonylamino)phenylboronic acid (1.0 eq.) and 3-bromo-6-methoxypicolinonitrile (from step 1) (1.0 eq.) in toluene (0.44 M) was mixed with tetrakis(triphenyl-phosphine)palladium (5 mol%) and 2N aqueous potassium carbonate solution (2.0 eq.). The reaction was heated to 1000C and stirred overnight. After cooling to ambient temperature, the reaction content was diluted with 2% methanol in dichloromethane and water. The two phases were separated, and the aqueous layer was extracted twice with 2% methanol in dichloromethane. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude product was purified by flash chromatography on a COMBIFLASH system (ISCO) using 0-50% ethyl acetate in hexane to give 3- methoxybenzo[f][l,7]naphthyridin-5-amme as a yellow solid. 1H NMR (acetone J-6): delta 8.91 (d, IH), 8.34 (d, IH), 7.63 (d, IH), 7.51-7.53 (dd, IH), 7.27-7.33 (m, 2H), 6.65 (br, 2H), 4.11 (s, 3H). LRMS [M+H] = 226.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1186637-43-3, 3-Bromo-6-methoxypicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; IRM LLC; NOVARTIS AG.; WO2009/111337; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 364793-93-1, 4-((6-Bromopyridin-3-yl)methyl)morpholine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a RB flask containing formylpyridine (9.347 g, 1 equiv.) in 175 mL 1,2-dichloroethane (3.5 mL/mmol) was added morpholine (4.7 mL, 1.07 equiv.) followed by NaBH(OAc)3 (14.819 g, 1.4 equiv.) and acetic acid (3.1 mL, 1.07 equiv.). The flask was loosely capped and the mixture was stirred at r.t. Mixture gets slightly warm. After 40 min, the reaction was quenched with saturated NaHCO3. When the gas evolution was greatly reduced, 1M NaOH was added to bring the pH to 8-9. The two layers were separated and the aqueous layer was extracted with DCM (×3). The organic layer was dried over Na2SO4, filtered and solvent was removed in vacuo. The product was filtered through silica with 1000 mL 100:1 EtOAc:NH4OH to remove baseline material. The material was dissolved in 15 mL EtOAc and 150 mL hexanes was added. The mixture was allowed to sit overnight at 4 C. to crystallize. The supernatant was decanted off and the crystals were washed with a little hexanes which was decanted off. The crystals were transferred to another flask using DCM. LC-MS showed only product. The solvent from the supernatant was removed in vacuo. The remaining mixture was purified by flash column (6.5×8.5 cm silica) using 500 mL 8:2 EtOAc; 1400 mL 100:1 EtOAc:NH4OH. All product fractions were combined giving 10.931 g (85%) of the 4-((6-bromopyridin-3-yl)methyl)morpholine as a yellow solid.In a RB flask, a mixture of 4-((6-bromopyridin-3-yl)methyl)morpholine (10.959 g, 1 equiv.), 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (10.478 g, 1.05 equiv.), 2M potassium phosphate solution (42.5 mL, 2 equiv.) and Pd(PPh3)4 (2.479, 0.050 equiv.)) in 210 mL dioxane (5 mL/mmol) was sparged with argon for 5 min. The flask was fitted with a septum and argon balloon and the mixture was stirred at 100 C. (amber solution). After 27 h, the mixture was allowed to cool then volume was reduced by at least half in vacuo. The remainder was diluted with water and extracted with EtOAc (×3). The organic layers were washed with brine, dried over Na2SO4, filtered and solvent was removed in vacuo. The material was purified by column chromatography on silica eluting with DCM:MeOH to give 10.268 g (85%) of 4-methyl-3-(5-(morpholinomethyl)pyridin-2-yl)aniline as a very viscous dark amber oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,364793-93-1, 4-((6-Bromopyridin-3-yl)methyl)morpholine, and friends who are interested can also refer to it.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; US2010/41642; (2010); 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. 6623-21-8, name is 4,6-Dimethylnicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 4,6-Dimethylnicotinonitrile

(i) 3-Cyano-4,6-dimethylpyrid-2-thione was prepared from 3-cyano-4,6-dimethylpyridine and thiourea following the procedure of Guerrara, Siracusa and Tornetta (Il, Farmaco Ed. Sc. 31 , 21, 1975), and was obtained as yellow needles, mp 245-250o.

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, 6623-21-8, 4,6-Dimethylnicotinonitrile.

Reference:
Patent; ICI AUSTRALIA LIMITED; EP104876; (1991); B1;,
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.18368-73-5, name is 3-Methyl-2-nitropyridine, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.name: 3-Methyl-2-nitropyridine

2-nitro 2-methylpyridine (4.2 g, 30.66 mmol) was dissolved in 100 mL of carbon tetrachloride,N-bromosuccinimide (5.5 g, 30.66 mmol) was added,Add the catalyst amount of the photoinitiator dibenzoyl peroxide, heat up to 100 C and reflux for 48 h.The reaction solution was returned to room temperature, the solvent was removed by distillation under reduced pressure, 50 mL of ice water was added,Extracted with ethyl acetate (40 mL X3). The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to a crude product. The crude product was purified by silica gel column chromatography (ethyl acetateEster: petroleum ether = 1: 10) 3-Bromoethyl-2-nitropyridine (2.9 g, 44.14%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-73-5, 3-Methyl-2-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Jiao Tong University; Fu Lei; Xie Dongsheng; Qiao Yixue; Liu Wenlu; Yu Jihao; (24 pag.)CN106749045; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem