Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 100202-78-6, 2-(Bromomethyl)-6-fluoropyridine, 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 2-(Bromomethyl)-6-fluoropyridine, blongs to pyridine-derivatives compound. Quality Control of 2-(Bromomethyl)-6-fluoropyridine

Preparation 45; ; [9-(6-Fluoro-pyridin-2-ylmethyl)-6-trifluoromethoxy-2,3,4,9-tetrahydro-lH- carbazol-3-yl]-carbamic acid benzyl esterAdd Cs2CO3 (6.44 g, 19.8 mmol) to a solution of (6-trifluoromethoxy-2,3,4,9-tetrahydro-lEta-carbazol-3-yl)-carbamic acid benzyl ester (Preparation 43) (4.00 g, 9.88 mmol) and 2-bromomethyl-6-fluoropyridine (Preparation 44) (3.11 g, 13.8 mmol) in DMF (40 mL). Heat the resulting mixture to 50 0C for 18 h and then dilute with EtOAc (120 mL). Wash the organics with water (3 x 40 mL), dry (MgSO4), filter, and concentrate to give the crude product (5.40 g) as a brown oil. Purify the crude product on silica gel (120 g) eluting with 25-45% EtOAc/hexanes to afford 2.85 g (56%) of the title compound as a tan oil. MS (ES): m/z 514 (M+l); HPLC (Method A): Rt = 4.54 min (95%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100202-78-6, 2-(Bromomethyl)-6-fluoropyridine, and friends who are interested can also refer to it.

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

Application of 83393-46-8, 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 83393-46-8, name is 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

Step a: 2-Bromo-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone is synthesized using commercially available 3-acetyl-7-azaindole in place of 1-imidazo[1,2-a]pyrimidin-3-yl-ethanone according to the procedure of example 71, step a.

According to the analysis of related databases, 83393-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JACKSON, Paul Francis; Manthey, Carl; Rhodes, Kenneth; Scannevin, Robert; Leonard, Kristi Anne; Barbay, Joseph Kent; Todd, Matthew; Springer, Barry A.; US2012/302573; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1193-71-1, 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. 1193-71-1, name is 4,6-Dimethylpyridin-3-amine. A new synthetic method of this compound is introduced below.

33: 1-(4-Methoxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (4,6-dimethyl-pyridin-3-yl)-amideTo a suspension of 1-(4-methoxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid IM51 (1.60 g, 5.38 mmol), 5-amino-2,4-dimethylpyridine (786 mg, 6.43 mmol) and triethylamine (3.00 mL, 21.5 mmol) in THF (20 mL) was added a 50% (w/w) solution of 1-propanephosphonic acid cyclic anhydride in THF (6.84 g, 10.7 mmol) drop wise over 10 min. The mixture was stirred at room temperature Overnight. The mixture was poured into water (20 mL). The THF was removed in vacuo. Aqueous NH3 solution was added to adjust pH to approximately 10 EtOH (25 mL) was added and the mixture was briefly heated to reflux and then left at room temperature overnight. The mixture was then cooled on an ice-water bath for 45 min and then filtered. The remanens was washed with water and dried in vacuo to give the title compound (1.41 g, 67%). 1H NMR (600 MHz, DMSO) delta 10.43 (s, 1H), 8.47 (s, 1H), 8.09-8.04 (m, 2H), 7.46 (s, 1H), 7.23 (s, 1H), 7.16-7.11 (m, 2H), 3.83 (s, 3H), 2.71 (s, 3H), 2.57 (s, 3H), 2.46 (s, 3H), 2.29 (s, 3H).LC-MS (m/z) 402.2 (MH+); tR=0.52.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1193-71-1, 4,6-Dimethylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; H. Lundbeck A/S; US2013/5743; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 136117-71-0, 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. 136117-71-0, name is (6-Bromoimidazo[1,2-a]pyridin-2-yl)methanol, molecular formula is C8H7BrN2O, 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.

Intermediate 38 (66.1 mg, 0.44 mmol) and (6-bromoimidazo[1 ,2-a]pyridin-2-yl)- methanol (100 mg, 0.44 mmol) were dissolved in acetonitrile (10 mL) and pyridiniumptoluenesulfonate (443 mg, 1.76 mmol) was added. The resulting mixture was heated at 80C overnight. The resulting mixture was cooled and evaporated onto silica. Purification by column chromatography (0-15% MeOH in DCM) gave a clear oil, whichwas freeze-dried to give the title compound (50 mg, 32%), 7:3 mixture of diastereomers, as a white solid.Major diastereomer (trans): H (400 MHz, DMSO-d6) 7.80 (dd, 1H, J0.6, 1.9 Hz), 7.57 (dd, 1H,J0.6, 8.8 Hz), 7.48 (m, 1H), 7.42 (m, 1H), 7.36 (dd, 1H,J9.5, 1.9 Hz), 7.29 (t, 1H,J7.3 Hz), 7.04 (d, 1H,J7.4 Hz), 6.97 (d, 1H,J2.5 Hz), 5.63 (qd, 1H,J6.3, 2.6 Hz), 5.22 (t, 1H, J5.7 Hz), 4.54 (m, 2H), 1.52 (d, 3H, J6.3 Hz.Minor diastereomer (cis): H (400 MHz, DMSO-d6) 7.78 (m, 1H), 7.57 (m, 1H), 7.48 (m, 1H), 7.42 (m, 1H), 7.36 (dd, 1H, J9.5, 1.9 Hz), 7.30 (t, 1H, J7.3 Hz), 6.92 (m,1H), 6.82 (d, 1H, J2.8 Hz), 5.40 (m, 1H), 5.28 (t, 1H, J5.7 Hz), 4.66 (d, 2H, J5.6 Hz),1.66 (d, 3H, J6.4 Hz). LCMS MH m/z 359.60.

According to the analysis of related databases, 136117-71-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; BROWN, Julien Alistair; CALMIANO, Mark Daniel; JONES, Elizabeth Pearl; KROEPLIEN, Boris; REUBERSON, James Thomas; SELBY, Matthew Duncan; SHAW, Michael Alan; ZHU, Zhaoning; WO2015/86512; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1190319-62-0, 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. 1190319-62-0, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one, molecular formula is C7H5BrN2O, 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.

Pottasium tert-butoxide (0.03 g, 0.27 mmol) was added to a suspension of 6-bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (preparation 30c, 0.87 g, 4.1 mmol) in dimethylsulphoxide (4 mL) and, after stirring for 10 minutes at room temperature, the mixture was heated to 40-45 C and methyl acrylate (1.14 mL, 12.71 mmol) was added dropwise over 60 minutes. After the addition, the mixture was stirred for 2 hours and then further potassium tert-butoxide (1.4 g, 12.21 mmol) was added portionwise over 30 minutes keeping the temperature below 50 C. The mixture was then heated to 100 C and stirred for 2 hours. Water (20 mL) was added and heating was continued at 85 C for 2 hours and then the mixture was left to cool overnight. Ethyl acetate was added and the mixture was washed with water, brine, dried (MgSO4) and evaporated to give the title compound (0.60 g, 50%) as a white solid. LRMS (m/z): 293/295 (M-1)+. 1H-NMR delta (CDCl3): 2.14 (m, 2H), 2.27 (m, 2H), 2.73 (m, 2H), 3.01 (m, 2H), 7.40 (d, J=1.5 Hz, 1H), 8.29 (d, J=1.5 Hz, 1H), 8.44 (brs, 1H).

According to the analysis of related databases, 1190319-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2108641; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53710-18-2, 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. 53710-18-2, name is 3,5-Diiodopyridine. A new synthetic method of this compound is introduced below.

In a 75-mL sealed tube, 3,5-diiodo-pyridine (intermediate A-5, 6.6 g, 20 mmol), 5-chloro- 3,3-dimethyl-2,3-dihydro-isoindol-1-one (intermediate A-3, 1.95 g, 10 mmol), CuT (571 mg, 3 mmol), K3P04 (4.24 g, 20 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.7 mL, 6 mmol) were dissolved in 20 mL of dioxane. The resulting reaction mixture was heated at120C for 3 hours before it was poured into water (50 mL) and extracted with EtOAc (2 x125 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4,filtered and concentrated in vacuo to give a crude product, which was purified by silica gelflash chromatography (0-30% EtOAc-hexane gradient) to yield the title compound (1.8 g,45%) as a light yellow solid. MS: 399.2 (M+Hj.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53710-18-2, 3,5-Diiodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191340; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 188057-20-7, 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. 188057-20-7, name is 4-Iodopyridin-3-ol. A new synthetic method of this compound is introduced below.

Step 35-4.; To a solution of 3-hydroxy-4-iodopyridine (5.09 g, 23.0 mmol) in DMF (95 mL) were added (R)-propylene carbonate (T95-A, 2.35 g, 23.0 mmol)) and potassium carbonate (3.18 g, 23.0 mmol). The solution was stirred at 85 C. for 72 h. Water was added and the aqueous phase extracted with EtOAc (3×). The combined organic phases were washed with brine (1×) and water (1×), dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (100% EtOAc) to give 1.4 g (24%) of T95-4(R).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,188057-20-7, 4-Iodopyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; Marsault, Eric; Fraser, Graeme L.; Benakli, Kamel; St-Louis, Carl; Rouillard, Alain; Thomas, Helmut; US2010/93720; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1026201-52-4, 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. 1026201-52-4, name is 5-Bromoimidazo[1,2-a]pyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below.

Step1:tert-Butyl5-bromoimidazo[1,2-a]pyridin-2-ylcarbamate.Toastirredsolutionof5-bromoimidazo[1,2-a]pyridine-2-carboxylicacid(1.00g,4.15mmol,1.0eq.)int-BuOH(20mL)andtoluene(20mL)wasaddedDPPA(1.37g,5.00mmol,1.2eq.)atanice-waterbathtemperature.Et3N(0.70mL,5.00mmol,1.2eq.)wasthenaddeddropwise.Theresultantmixturewasheatedtorefluxfor14hrs.TLCindicatedthedisappearanceof5-bromoimidazo[1,2-a]pyridine-2-carboxylicacid.Thecrudereactionmixturewasconcentratedtodryness.Theresiduewaspurifiedbyacolumnchromatography(200-300meshsilicagel,PE/EA5/1)toaffordtert-butyl5-bromoimidazo[1,2-a]pyridin-2-ylcarbamate.1HNMR(400MHz,DMSO-d6)delta(ppm)10.14(br,1H),7.82(s,1H),7.47(d,J8.7Hz,1H),7.24(d,J6.8Hz,1H),7.16-7.20(m,1H),1.49(s,9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1026201-52-4, 5-Bromoimidazo[1,2-a]pyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; JN THERAPEUTICS; LI, Jin; WU, Shung; YANG, Minmin; CHEN, Sean; HAO, Wenshan; (148 pag.)WO2016/119700; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 90145-48-5, 5-Bromopyridine-2-carboxamide, 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, Formula: C6H5BrN2O, blongs to pyridine-derivatives compound. Formula: C6H5BrN2O

Description 9: 5-bromopicolinonitril D9)Phosphorus oxychloride (1 1 1 g, 0.720 mol) was added to a mixture of 5- bromopicolinamide (D8) (58 g, 0.288 mol) in dry toluene (300ml) The mixture was heated to reflux for 2 hours. The mixture was poured into ice/water, and basified to pH=12 with 2N NaOH. The resulting mixture was extracted with ethyl acetate and the organic phase was washed with brine, dried over Na2S04, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 10:1 . Collected fractions, after solvent evaporation afforded the title compound (D9) (43.6 g) as a yellow solid.1 HNMR (400 MHz, CHLOROFORM-d) delta (ppm): 7.60 (d, J = 8.4 Hz, 1 H), 8.00 (dd, J = 6.0, 2.0 Hz, 1 H), 8.79 (d, J = 2.0 Hz, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90145-48-5, 5-Bromopyridine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 84199-61-1, 3-Acetyl-2-bromopyridine, 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, Formula: C7H6BrNO, blongs to pyridine-derivatives compound. Formula: C7H6BrNO

Synthesis of 7-phenylquinolin-5-ol (6.1) for Example 1[0271] 3-Acetyl-2-bromopyridine, 56 muL phenylacetylene, 170 muL DIPEA, 22.5 mg triphenylphosphinpalladium(II) chlorid, 3 mg Cu(I)I were suspended in 1 mL DMF under argon atmosphere and stirred for 16 h at 25 C. The mixture was diluted with DCM and extracted with diluted aq. NH3 and brine. The organic phase was concentrated and the mixture separated via flash chromatography (10 g SiO2, cyclohexane?cyclohexane/ethylacetate 70:30) to yield 40 mg 1-(2-(phenylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS: Rt=1.21 min (method E), M+H=222

The synthetic route of 84199-61-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; McCARTHY, Clive; SCOTT, John; US2013/29949; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem