Category: pyridine-derivatives

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 14294-11-2, name is 1-(Pyridin-2-yl)thiourea. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 14294-11-2

According to Scheme 3 Step 4: A solution of 2-bromo-1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)propan-1-one (23.8 mmol, 7.70 g) and of 1-(pyridin-2-yl)thiourea (26.2 mmol, 4.02 g) in EtOH (200 mL) was stirred under reflux overnight. The reaction was quenched with water (200 mL) and the aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated to yield a brown solid. The resulting crude product was purified by flash chromatography over silica gel using DCM/AcOEt (98:2) as eluent to yield after evaporation 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-methyl-N-(pyridin-2-yl)thiazol-2-amine (20.7 mmol, 7.80 g, 87%) as a beige solid.LC (Zorbax SB-C18, 3.5 mum, 4.6×50 mm Column): RT=2.29 min; MS m/z ES+=378.

With the rapid development of chemical substances, we look forward to future research findings about 14294-11-2.

Reference:
Patent; Bolea, Christelle; Calanire, Sylvain; US2010/144756; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 866546-07-8 ,Some common heterocyclic compound, 866546-07-8, molecular formula is C7H5ClN2, 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 4 ~~ Preparation of[3-benzyloxy-2-cyclopropylmethoxy-phenyl]-(5-chloro-lH-pyrrolo[2,3- b]pyridin-3-yl)-methanol (131):[0206] A mixture of 5-chloro-lH-Pyrrolo[2,3-6]pyridine (4, 0.68 g, 4.46 mmol), 3-benzyloxy-2- cyclopropylmethoxy-benzaldehyde (130, 1.2 g, 4.25 mmol), and potassium hydroxide (0.68 g, 1 1 mmol) in methanol (50 mL) was stirred at room temperature for 4 days. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was collected, washed with brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide compound as a white solid (131, 0.99g, 54%). MS(ESI) [M+H’]’ = 435.21.

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. 866546-07-8, 5-Chloro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PLEXXIKON, INC.; WO2008/80001; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 83004-10-8 ,Some common heterocyclic compound, 83004-10-8, molecular formula is C6H5Br2N, 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.

Synthesis of N-((6-Bromopyridin-2-yI)methyl)-N-(1-isopropylpiperidin-4-yI)-4-(4-(trifluoromethyl)phenyl)pyrimidin-2-amineTo an ice-cooled solution of (1 -isopropyl-piperid in-4-yl)-[4-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-amine (1.00 g, 2.74 mmol, 1.0 eq.) in DMF (15 mL), sodium hydride 60%dispersion in mineral oil (154 mg, 3.84 mmol, 1.4 eq.) was added. The resulting orange mixture was stirred at r.t. for 2 hours. Then a solution of 2-bromo-6-(bromomethyl)pyridine (757 mg, 3.02 mmol, 1.1 eq.) in DMF (5 mL) was added dropwise and the mixture was stirred at 60 C for 18 hours. The mixture was cooled to 0 C and sodium hydride 60%dispersion in mineral oil (77 mg, 1.92 mmol, 0.7 eq.) was added. The resulting orange mixture was stirred at r.t. for 2 hours. Then a solution of 2-bromo-6-(bromomethyl)pyridine (378 mg, 1.51 mmol, 0.55 eq.) in DMF (2 mL) was added dropwise and the mixture was stirred at 60 C 4 hours. The reaction mixture was quenched with sat. aq. Na2CO3 solution. The mixture was extracted with DCM. The comb. org. phases were washed with water, sat.aq. NaCI soln., dried over MgSO4, and concentrated in vacuo. The residue was purified by flashmaster (column: 50 g, flow: 40 mL/min, 35 fractions of 45 mL, Hept/AcOEt-NEt3 (10% NEt3) 95:5 to Hept/AcOEt-NEt3 (10% NEt3) 1:1) to afford the title compound as an orange oil.LC-MS 4: tR = 0.82 mm; [M+H] = 534.2

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. 83004-10-8, 2-Bromo-6-(bromomethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; CIANA, Claire-Lise; KIMMERLIN, Thierry; SIEGRIST, Romain; WO2015/28989; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1256823-65-0 ,Some common heterocyclic compound, 1256823-65-0, molecular formula is C6H2BrClN2, 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 5-bromo-6-chloropicolinonitrile (5 g, 22.99 mmol) and tributyl (1-ethoxyvinyl) stannane (8.30 g, 22.99 mmol) in toluene (10 mL) was added tetrakis (triphenyl-phosphine) palladium (0) (0.531 g, 0.460 mmol) and the mixture was stirred at 110 under N2for 16h. The mixture was cooled to rt and conc. HCl (1.888 mL, 22.99 mmol) was added to the mixture. The grey mixture was stirred at 25 for 1h. The mixture was diluted with water (10 mL) and extracted with ethyl acetate (15 mL x 3) . The combined organic layers were washed with brine (10 mL x 2) , dried over sodium sulfate, filtered and the filtrate was concentrated in vacuum. The residue was purified by column chromatography (SiO2, petroleum ether: ethyl acetate from 10: 1 to 3: 1) to give the title compound.1HNMR (CDCl3, 400 MHz) delta: 7.99 (d, J 8.0 Hz, 1H) , 7.73 (d, J 7.6 Hz, 1H) , 2.72 (s, 3H) .

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. 1256823-65-0, 5-Bromo-6-chloropicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; BAO, Jianming; HENDERSON, Timothy J.; LO, Michael Man-chu; MAZZOLA, JR., Robert D.; RUDD, Michael T.; TELLERS, David M.; TONG, Ling; LI, Chunsing; NA, Meng; (144 pag.)WO2019/238; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 149489-32-7, 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 149489-32-7, name is 2-(Chloromethyl)-3-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 182; N-[6-Cyano-9-(3-fluoro-pyridin-2-ylmethyl)-2,3,4,9-tetrahydro-lH-carbazol-3-yl]- isobutyramideSuspend sodium hydride (60% suspension in mineral oil, 114 mg, 1.64 mmol) in dimethylformamide (7 mL) and cool to 0 0C. Add a solution of N-(6- cyano-2,3,4,9-tetrahydro-lH-carbazol-3-yl)-isobutyramide (Preparation 3) (385 mg, 1.37 mmol) in dimethylformamide (3.5 mL). After several minutes, warm the reaction to room temperature, and stir for 30 min, after which time add 2- chloromethyl-3-fluoro-pyridine (Preparation 60). Stir the reaction overnight and then dilute with ethyl acetate (100 mL). Wash the reaction mixture sequentially with brine (3 x 75 mL), water (75 mL), and brine (75 mL). Separate the organic layer, dry over magnesium sulfate, filter, and concentrate under reduced pressure. Purify using flash chromatography [silica gel, gradient from 0: 100 to 20:80 (90: 10: 1 EPO dichloromethane:methanol:concentrated ammonium hydroxide) :dichloromethane] to provide 184 mg (38%) of the title compound as an off-white solid, m.p. = 213- 216 0C; MS: m/z 391 [C23H23FN4O + I]+; 1H NMR (300 MHz, DMSO-J6): delta 8.29- 8.31 (m, IH), 7.92 (d, /= 1.2 Hz, IH), 7.84 (d, / = 7.6 Hz, IH), 7.71-7.78 (m, IH), 7.58 (d, / = 8.5 Hz, IH), 7.38-7.44 (m, 2H), 5.56 (s, 2H), 3.99-4.04 (m, IH), 2.73- 3.00 (m, 3H), 2.49-2.55 (m, IH), 2.37 (septet, J= 6.8 Hz, IH), 1.96-2.00 (m, IH), 1.76-1.83 (m, IH), 1.01 (d, /= 6.8 Hz, 6H).

According to the analysis of related databases, 149489-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/2181; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59786-31-1 ,Some common heterocyclic compound, 59786-31-1, molecular formula is C7H6BrNO2, 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 115a. To a solution of methyl 3-bromoisonicotinate (0.2 g, 0.93 mmol, 1.0 equiv) in Dioxane (10 mL) was added benzenethiol (0.204 g, 1.85 mmol, 2.0 equiv), KOAc (0.184 g, 1.876 mmol, 2.0 equiv) and resulting reaction mixture purged with N2 gas for 10 minute, followed by the addition of Pd2(dba)3 (0.042 g, 0.046 mmol. 0.05 equiv), Xanthphose (0.026 g, 0.046 mmol, 0.05 equiv) and resulting reaction mixture). The resulting reaction mixture was heated at 90 C. for overnight. Product formation was confirmed by LCMS. After the completion of reaction, the mixture was filtered through celite bed, washed with ethyl acetate (100 mL). Filtrate was concentrated under reduced pressure. The crude product obtained was purified by flash chromatography (20% ethyl acetate hexane as an eluent) to obtain methyl 3-(phenylthio)isonicotinate (0.100 g, 44.4% Yield) as yellow oil. (0939) LCMS 246.1 [M+H]+ (0940) 1H NMR (400 MHz, DMSO-d6) delta 8.92 (br. s., 1H), 8.76-8.56 (m, 2H), 7.50 (s, 1H), 7.48-7.40 (m, 2H), 7.40-7.29 (m, 2H), 5.14-5.04 (m, 1H), 4.21 (br. s., 1H), 4.03 (d, J=2.6 Hz, 2H), 2.87 (br. s., 1H), 2.79 (d, J=14.5 Hz, 1H), 2.67 (br. s., 1H).

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. 59786-31-1, Methyl 3-bromoisonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Praxis Biotech LLC; ALFARO, Jennifer; BELMAR, Sebastian; BERNALES, Sebastian; PUJALA, Brahmam; PANPATIL, Dayanand; BHATT, Bhawana; US2019/185451; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 156118-16-0, 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. 156118-16-0, name is 3-Amino-6-bromo-4-methylpyridine, molecular formula is C6H7BrN2, 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.

Step 2 [0611] To a suspension 6-bromo-4-methylpyridin-3 -amine (XV) (186 g, 994 mmol, 1.00 eq) and KOAc ( 1 15 g, 1.17 mol, 1.18 eq) in CHC13 (3.50 L) was added Ac20 (405 g, 3.97 mol, 3.99 eq) and the suspension was stirred at 25C for 1 h and then heated at 60-70C to reflux for an additional 2 h. After cooling the suspension to 25C, isopentyl nitrate (233 g, 1.99 mol, 2.00 eq) and 18-crown-6 (21 g, 79.5 mmol, 0.08 eq) was added and the suspension heated to reflux for 12 h. After cooling to 25C, the suspension was filtered and the filtrate was concentrated under reduced pressure to yield a residue that was treated with a suspension of potassium carbonate (450 g) in a solution of methanol and water (450 mL) at 0C for 3 h. The suspension was concentrated under reduced pressure to yield a residue that was extracted with EtOAc (1000 mL x 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 5-bromo-lH-pyrazolo[3,4-c]pyridine (XVI) (200 g, crude) as yellow solid. The crude product was used for the next step without any purification. NMR (DMSO- tf, 400 MHz) delta ppm 7.96 (s, 1H), 8.15 (s, 1H), 8.86 (s, 1H); ESIMS found for C6H4BrN3 mlz 198.3 (M+H).

According to the analysis of related databases, 156118-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (261 pag.)WO2017/23984; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 101990-70-9, name is 5-(Chloromethyl)-2-methoxypyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H8ClNO

A mixture of N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (Intermediate 13), (120 mg), 5-(chloromethyl)-2-methoxypyridine (69 mg) and cesium carbonate (329 mg) in DMF (3.9 mL) was stirred at rt overnight. A further 20 mg 5-(chloromethyl)-2-methoxypyridine was added and stirred for 2days. A further 100 mg 5-(chloromethyl)-2-methoxypyridine was added and stirred for 24 h. Water (20 mL) was added and the reaction mixture was extracted with EtOAc (3*20 mL). The combined organic layers were washed with brine (20 mL) and dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by column chromatography to give the desired compound (131 mg). LCMS: m/z 395.49 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.15-1.52 ppm (m, 4H) 1.71 (d, J=9.9 Hz, 2H) 2.05 (t, J=9.0 Hz, 2H) 2.50 (s, 3H) 3.16 (br. s., 1H) 3.49 (td, J=9.7, 4.3 Hz, 1H) 3.71-3.84 (m, 1H) 3.83 (s, 3H) 5.43 (s, 2H) 6.62 (d, J=8.6 Hz, 1H) 6.84 (d, J=4.8 Hz, 1H) 7.10 (dd, J=8.6, 2.1 Hz, 1H) 7.79 (d, J=1.8 Hz, 1H) 7.95 (s, 1H) 8.25 (d, J=4.6 Hz, 1H) 9.24 (d, J=7.0 Hz, 1H)

The synthetic route of 101990-70-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Payne, Andrew; Castro Pineiro, Jose Luis; Birch, Louise Michelle; Khan, Afzal; Braunton, Alan James; Kitulagoda, James Edward; Soejima, Motohiro; US2015/94328; (2015); 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. 45644-21-1, name is 2-Amino-6-chloropyridine. A new synthetic method of this compound is introduced below., Quality Control of 2-Amino-6-chloropyridine

To a solution of 6-chloropyridin-2-amine (50.0 g, 389 mmol) in DMF (700 mL) was added N-iodosuccinimide (105 g, 467 mmol). The brown solution was stirred at rt for 12 h. The mixture was poured into water (2.1 L) and filtered. The filter cake was washed with water (2*500 mL) and then dried under vacuum. Purification (FCC, SiO2; 5-20% EtOAc/petroleum ether) afforded the title compound (83 g, 75%) as a pink solid. MS (ESI): mass calcd. for C5H4ClIN2, 253.9; m/z found, 254.7 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.74 (d, J=8.0 Hz, 1H), 6.20 (d, J=8.0 Hz, 1H), 4.69 (br s, 2H).

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, 45644-21-1, 2-Amino-6-chloropyridine.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Gyuris, Mario; Laforteza, Brian Ngo; Lebold, Terry Patrick; Meyer, Stephen Todd; Ravula, Suchitra; Savall, Brad M.; Shireman, Brock T.; Wade, Warren Stanfield; Gerencser, Janos; (87 pag.)US2018/111933; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 69627-02-7, 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. 69627-02-7, name is Thieno[3,2-b]pyridin-7(4H)-one, molecular formula is C7H5NOS, 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.

Example 1; Preparation of N-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide; Step A: Preparation of 7-chlorothieno[3,2-b]pyridine; To a stirred solution of POCl3 (28.6 mL, 313 mmol) in 1,2-dichloroethane (200 mL) was added commercially available thieno[3,2-b]pyridin-7-ol (94.7 g, 626 mmol) as a powder in one portion. The reaction was stirred for 2 hours at reflux under N2. The mixture was concentrated, using toluene (3×100 mL) to azeotrope. The dark residue was resuspended in CH2Cl2 (1 L), and a saturated aqueous solution of NaHCO3 (500 mL) was carefully added. The mixture was stirred for 30 minutes until bubbling had ceased. The biphase was separated, and the aqueous was re-extracted with CH2Cl2 (500 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated, to obtain a brown oil, which crystallized upon standing (38.4 g, 71%). 7-Chlorothieno[3,2-b]pyridine has also been prepared using oxalyl chloride (WO 99/24440). 1H NMR (400 MHz, CDCl3) delta 8.61 (d, J=5 Hz, 1H), 7.80 (d, J=6 Hz, 1H), 7.60 (d, J=6 Hz, 1H), 7.29 (d, J=5 Hz, 1H).

According to the analysis of related databases, 69627-02-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Blake, James F.; Boyd, Steven; De Meese, Jason; Gaudino, John J.; Marlow, Allison L.; Seo, Jeongbeob; Thomas, Allen A.; Tian, Hongqi; US2007/197537; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem