Category: 628691-93-0

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.628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid, molecular formula is C6H3ClFNO2, molecular weight is 175.55, as common compound, the synthetic route is as follows.Product Details of 628691-93-0

Step l :A suspension of 2-chloro-3-fluoropyridine-4-carboxylic acid (CAS 628691-93-0, 2 g, 11.39 mmol) in MeOH (7 mL) and DCM (21 mL) at 0 C was treated with TMS-Diazomethane (5.70 mL, 11.39 mmol) in a drop wise fashion. The reaction was stirred at 0 C for 0.5 h. The reaction was quenched with AcOH (0.5 mL) and concentrated in vacuo. The residue was purified by flash chromatography (0-100% EtOAc in petrol on Si02) to afford methyl 2-chloro-3-fluoropyridine-4-carboxylate. 1H NMR (300 MHz, Methanol-^) delta ppm 3.97 (s, 3 H) 7.76 – 7.86 (m, 1 H) 8.29 – 8.40 (m, 1 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,628691-93-0, 2-Chloro-3-fluoroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; AHMED, Saleh; BARKER, Gregory; CANNING, Hannah; DAVENPORT, Richard; HARRISON, David; JENKINS, Kerry; LIVERMORE, David; WRIGHT, Susanne; KINSELLA, Natasha; (259 pag.)WO2016/148306; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 628691-93-0, Adding some certain compound to certain chemical reactions, such as: 628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid,molecular formula is C6H3ClFNO2, 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 628691-93-0.

In a 500 mL one necked round bottom flask 2-chloro-3-fluoroisonicotinic acid (25.0 g, 142 mmol) was dissolved in thionyl chloride (300 mL). DMF (1 mL) was added to the solution and the mixture was heated to reflux for 2 hours. The solution was concentrated in vacuo resulting in a pale yellow oil. The oil was added to CH2C12 (130 mL) and cooled to 0C. MeOH (18.3 g, 570 mmol) was added drop wise to the solution. After addition the solution was allowed to warm to room temperature and stirred for 16 hours. The solution was cooled to 0C and saturated NaHC03 was added. The pH went to about 7. The organic layer was washed with water (2 X 100 mL), brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo to give methyl 2-chloro-3-fluoro-pyridine-4-carboxylate (24.8 g) as a pale brown solid. In a 500 mL one necked round bottom flask, to a solution of methyl 2-chloro-3-fluoro-pyridine- 4-carboxylate (24.8 g, 131 mmol) in DMF (250 mL) was added potassium vinyltrifluoroborate (26.3 g, 196 mmol), potassium carbonate (21.7 g, 157 mmol) and (0687) tetrakis(triphenylphosphine)palladium(0) (9.07 g, 7.85 mmol). The mixture was stirred at reflux for 16 hours. The reaction mixture was filtered and the filtrate was dissolved in CH2C12 (100 mL) and washed with water (3 X 200 mL), brine, dried over Na2S04 and filtered. The filtrate was concentrated to give the crude product. This crude was combined with a second identical batch and purified on silica gel (EtO Ac/petroleum ether 0% – 20%) resulting in methyl 3-fluoro- 2-vinyl-pyridine-4-carboxylate (16 g) as a brown oil.

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. 628691-93-0, 2-Chloro-3-fluoroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 628691-93-0, 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 628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Step 1. 3-fluoro-2-vinylisonicotinic acidA solution of 2-chloro-3-fluoroisonicotinic acid (1.50 g, 8.55 mmol, Matrix), dibutyl vinylboronate (2.82 mL, 12.8 mmol, Aldrich), and potassium carbonate (1.42 g, 10.25 mmol) in N,N-dimethylacetamide (9 mL) and water (3 mL) was degassed by bubbling a stream of nitrogen through the solution for 20 minutes.Tetrakis(triphenylphosphine)palladium(0) (0.59 g, 0.51 mmol) was added and the mixture was similarly degassed for a further 10 minutes. The reaction vessel was sealed and heated in the microwave for 25 minutes at 135 C. The reaction mixture was filtered and purified using preparative HPLC (UV-detection) eluting with a gradient ofH20/MeCN containing 0.1% TFA. This reaction was run again on the same scale and the product of both runs were pooled. Solvent was removed from the eluent containing desired product in vacuo (1.3 g, 46%). 1H NMR (300 MHz, CD3OD): delta 8.45 (d, 1H), 7.69 (dd, 1H), 7.07 (ddd, 1H), 6.44 (dd, 1H), 5.65 (dd, 1H); 19F NMR (282 MHz, CD3OD): delta -129.64 (d, IF); LCMS (M+H)+: 167.9.

According to the analysis of related databases, 628691-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; RODGERS, James D.; SHEPARD, Stacey; ZHU, Wenyu; SHAO, Lixin; GLENN, Joseph; WO2012/68450; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 628691-93-0, 2-Chloro-3-fluoroisonicotinic acid, 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, Safety of 2-Chloro-3-fluoroisonicotinic acid, blongs to pyridine-derivatives compound. Safety of 2-Chloro-3-fluoroisonicotinic acid

To a mixture of 2- chloro-3-fluoro/5onicotinic acid (3.55 g, 20.2 mmol) and triethylamine (8.4 mL, 6.13 g, 60.6 mmol) in dry toluene (40 mL) and dry 7-BuOH (40 mL) under nitrogen, was added diphenylphosphoryl azide (6.51 mL, 8.27 g, 30.1 mmol). The reaction was heated at 110 C for 3 hours then cooled to ambient temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in DCM (50 mL) and washed with water (40 mL). The aqueous phase was extracted with DCM (2 x 40 mL) and the combined organic extract was dried over MgS04, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-20 % EtOAc in DCM) to give the title compound as a yellow oil (3.8 g, 71 % yield). NMR (400 MHz, CDC13): delta 8.09-8.07 (m, 2H), 6.98 (br s, 1H), 1.54 (s, 9H).

The synthetic route of 628691-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 628691-93-0 ,Some common heterocyclic compound, 628691-93-0, molecular formula is C6H3ClFNO2, 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.

.-Benzyl-6-chloro-7-fluoro- 1 H-spiro [furo [3 ,4-c]pyridine-3 ,4′ -piperidin] – 1 -one2 3To a solution of 2,2,6,6-tetramethylpiperidine (72 g, 0.51 mol) in 200 ml of anhydrous THF under nitrogen at -78C was added n-BuLi (270 ml, 0.68 mol). After stirring for 0.5 h, the resulting mixture was added to a solution of 2-ch]oro-3-fluoropyridine-4-carboxylic acid (35 g, 0.2 mol) in 80 ml of anhydrous THF under nitrogen at -78C. After stirring for 3 h, the reaction mixture was added a solution of l-benzyl-piperidin-4-one (38 g, 0.20 mol) in 50 ml of THF under nitrogen at -78C. After stirring at -78C for 2 h, and room temperature for 1 h5 the reaction was quenched with 2 M aqueous hydrochloride (final pH = ca 2). The mixture was stirred at room temperature overnight, and the pH was adjusted to 9-10 with 2 M aq sodium hydroxide. The product was extracted with ethyl acetate (3x 500 mL), and the combined extracts were washed with brine, dried over Na2S0 j filtered and concentrated. The residue was purified by eluting on a silica gel column with PE: EtOAc = 3:1 to give the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,628691-93-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD K.K.; LIN, Linus, S.; SUZUKI, Takao; WO2011/37771; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 628691-93-0 , The common heterocyclic compound, 628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid, molecular formula is C6H3ClFNO2, 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.

A mixture of lithium diisopropylamide (2M in heptane/ tetrahydrofuran/ethylbenzene-stabilised with magnesium bis- (diisopropylamide), 16. 7 ml) and tetrahydrofuran (30 ml) was cooled to [- 78C] and [A PRE-COOLED (-78C)] solution of 2-chloro-3-fluoropyridine (4.0 g, 30.4 mmol) in tetrahydrofuran (30 ml) was added dropwise over 20 min. After 3 h, carbon dioxide was bubbled through the cold reaction mixture for 20 min. The reaction was then warmed [TO-30C] for 1 h then warmed [TO 0C.] The mixture was quenched by the addition of water (75 [ML).] The aqueous phase was washed with diethyl ether (100 ml), then the pH of the solution adjusted to 2 by the addition of 2N hydrochloric acid. The resulting white precipitate was aged for 18 h then filtered and left to air- dry, which afforded [2-CHLORO-3-FLUOROISONICOTINIC] acid as a white solid (4.22 g, 79%): 8H (360 MHz, DMSO) 7. 80 [(1H,] dd, J 5 and 5), 8. 39 [(1H,] d, J 5), 14.20 [(1H,] s). [2-CHLORO-3-FLUOROISONICOTINIC] acid (3.30 g, 18.8 mmol) was suspended in thionyl chloride (40 ml) and heated under reflux for 2.5 h. The solvent was evaporated and the residue dried by means of azeotropic removal of water with toluene (100 ml) to afford a pale yellow oil. The oil was dissolved in dichloromethane (20 ml) and cooled to 0C before methanol (2.42 g, 75.3 mmol) was added dropwise to the solution over 15 min. On complete addition the mixture was allowed to warm to ambient temperature and stirred for [18] h. The solvent was evaporated and the mixture partitioned between water (75 ml) and dichloromethane (100 ml). The aqueous phase was extracted further with dichloromethane (100 ml), the organic layers were combined, washed with brine (75 ml), dried over anhydrous sodium sulphate, filtered and evaporated to give 2-chloro-3- fluoroisonicotinic acid methyl ester (3.32 g, 93%) as a pale yellow solid: [SN] (360 MHz, [CDCL3)] 3.99 (3H, s), 7.70 [(1H,] dd, J 5 and 5), 8. 31 [(1H,] d, J 5). [2-CHLORO-3-FLUOROISONICOTINIC] acid methyl ester (3.32 g, 17.5 mmol) was converted to 8-fluoroimidazo [[L,] 2-a] pyridine-7-carboxylic acid methyl ester (1.4 g, 41%) as described in Example 1. [8-FLUOROIMIDAZO] [1, 2-a] [PYRIDINE-7-CARBOXYLIC] acid methyl ester (0.19 g, 1.0 mmol) was brominated as described in Example [1,] affording 3- [BROMO-8-FLUOROIMIDAZO] [1, 2-a] pyridine-7-carboxylic acid methyl ester (195 mg, 71%): [8H] (360 MHz, CDCl3) 4.00 (3H, s), 7. 32 [(1H,] t, [J 6.] 9), 7.43 (1H, dd, [J 7] and 6), 8. 19 [(1H,] s), 8. 37 [(1H,] d, [J 7).] 3-Bromo-8-fluoroimidazo [[L,] 2-a] pyridine-7-carboxylic acid methyl ester (0.10 g, 0.37 mmol) and 4, [2′-DIFLUORO-5′- (5,] 5-dimethyl- [1, 3,2] [DIOXABORINAN-2-YL) BIPHENYL-2-CARBONITRILE] (0.15 g, 0.44 mmol) were coupled following the procedure in Example 1 to afford 3- (2′-cyano-2, 4′- difluorobiphenyl-5-yl) -8-fluoroimidazo [1, 2-a] pyridine-7-carboxylic acid methyl ester (79 mg, 53%) as a white solid: [6H] (400 MHz, CDCl3) 4.00 (3H, s), 7.35 [(1H,] dd, J 7 and 7), 7.34-7. 46 (2H, [M), 7. 53-7.] 66 (4H, m), 7.85 (1H, [S),] 8. 24 [(1H,] [D,] J [7)] ; m/z [(ES+)] 408 [(100%,] [MHZ+).]

The synthetic route of 628691-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2003/99816; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 628691-93-0, 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.628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid, molecular formula is C6H3ClFNO2, molecular weight is 175.55, as common compound, the synthetic route is as follows.

1.15.1. Step i: tert-butyl N-(2-chloro-3-fluoro-4-pyridyl)carbamate1002621 Diphenylphosphoryl azide (DPPA) (129 mmol) was added to a mixture of 2-chloro-3-fluoro- pyridine-4-carboxylic acid (85.7 mmol), Et3N (257 mmol) in 1:1 tert-BuOH/toluene (200 mL). The mixture was heated at 110C for 4 h. Mixture was diluted with H20 and extracted with DCM. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (Si02, 100:0 to 80:20 DCM/EtOAc) to yield the desired product tert-butyl N-(2-chloro- 3 -fluoro-4-pyridyl)carbamate.

The chemical industry reduces the impact on the environment during synthesis 628691-93-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; BLANC, Javier; OR?ULIC, Mislav; RO?CIC, Maja; WO2015/110378; (2015); 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.628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid, molecular formula is C6H3ClFNO2, molecular weight is 175.55, as common compound, the synthetic route is as follows.Product Details of 628691-93-0

Step i: tert-butyl N-(2-chloro-3-fluoro-4-pyridyl)carbamate Diphenylphosphoryl azide (DPPA) (129 mmol) was added to a mixture of 2-chloro-3-fluoro-pyridine-4-carboxylic acid (85.7 mmol), Et3N (257 mmol) in 1:1 tert-BuOH/toluene (200 mL). The mixture was heated at 110 C. for 4 h. Mixture was diluted with H2O and extracted with DCM. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (SiO2, 100:0 to 80:20 DCM/EtOAc) to yield the desired product tert-butyl N-(2-chloro-3-fluoro-4-pyridyl)carbamate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,628691-93-0, 2-Chloro-3-fluoroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; MENET, Christel Jeanne Marie; MAMMOLITI, Oscar; BLANC, Javier; ORSULIC, Mislav; ROSCIC, Maja; US2015/203455; (2015); 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. 628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Chloro-3-fluoroisonicotinic acid

Step A: A mixture of 2-chloro-3-fluoroisonicotinic acid (2.0 g, 10.0 mmol) in thionyl chloride (42 mL) was heated to 80 0C. The homogenous solution was stirred for 2 hours, concentrated under reduced pressure, and pumped dry on high vacuum overnight to give crude 2-chloro-3-fluoroisonicotinoyl chloride. Crude 2-chloro-3-fluoroisonicotinoyl chloride (1.04 g, 5.4 mmol) was added to a stirred solution of JV-(3-amino-2-chloro-4-fluorophenyl)-7V-(4- methoxybenzyl)propane-l -sulfonamide (2.08 g, 5.4 mmol) in anhydrous CHCl3 (15 mL), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched by adding sat. aqueous NaHCO3 solution, followed by extraction with DCM (3X). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified using flash chromatography (gradient elution, solvent: 0-50% ethyl acetate in heptanes) to afford 2-chloro- LambdaL(2-chloro-6-fluoro-3-(N-(4-methoxybenzyl)propylsulfonamido)phenyl)-3- fluoroisonicotinamide (2.75 g, 94%). 1H NMR (500 MHz, DMSO-^6) delta 10.67 (s, IH), 8.44 (d, IH), 7.71 (t, IH), 7.35 (m, 2H), 7.13 (t, 2H), 6.82 (dd, 2H), 4.81 (d, IH), 4.63 (d, IH), 3.70 (s, 3H), 3.37 – 3.20 (m, 2H), 1.80 (d, 2H), 1.01 (dt, 3H). LC/MS: m/z 544.1 [M+l].

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, 628691-93-0, 2-Chloro-3-fluoroisonicotinic acid.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; ZHAO, Guiling; BUCKMELTER, Alexandre J.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark; WO2011/25938; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem