Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 175204-82-7, Methyl 4-(trifluoromethyl)nicotinate, 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, Computed Properties of C8H6F3NO2, blongs to pyridine-derivatives compound. Computed Properties of C8H6F3NO2

Step 1. To a stirred suspension of LAH (0.64 g, 17.0 mmol) in THF (30 mL) at -78 C. was added dropwise methyl 4-trifluoromethylnicotinate (1.74 g, 8.48 mmol) in THF (20 mL). The mixture was stirred for 1 h then carefully quenched with aqueous NaHCO3 (80 mL) and extracted with CH2 Cl2 (3*100 mL). The combined organic extracts were dried (Na2 SO4) and concentrated in vacuo to give 3-hydroxymethyl-4-trifluoromethylpyridine as an oil (TLC: Rf = 0.35 (1:1 hexane:EtOAc)).

The synthetic route of 175204-82-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5756497; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1235036-15-3 ,Some common heterocyclic compound, 1235036-15-3, molecular formula is C10H11BrClNO2, 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 Example 1.1.10 (100 mg) and tert-butyl 3-bromo-6-chloropicolinate (52.5 mg) in dioxane (2 mL) was added tris(dibenzylideneacetone)dipalladium(0) (8.2 mg), K3P04 (114 mg), 1,3,5,7- tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (5.24 mg) and water (0.8 mL). The mixture was stirred at 95 C for 4 hours, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over Na2S04, filtered, concentrated and purified by flash chromatography, eluting with 20% ethyl acetate in heptanes and then with 5% methanol in dichloromethane, to provide the title compound. MS (ESI) m/e 643.3 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1235036-15-3, its application will become more common.

Reference:
Patent; ABBVIE INC.; BENATUIL, Lorenzo; BRUNCKO, Milan; JUDD, Andrew, S.; LI, Yingchun; MCCLUSKEY, Andrew; PHILLIPS, Andrew, C.; PHILLIPS, Darren, C.; SEAGAL, Jane; SOUERS, Andrew, J.; (608 pag.)WO2017/214458; (2017); A2;,
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. 887707-23-5, name is 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H3F3INO

A solution of 2-hydroxy-3-(trifluoromethyl)pyridine C in a mixture of N-iodosuccinimide (NIS), acetonitrile, and dimethylformamide (DMF) is heated at 80 C. for 2 hours to produce 2-hydroxy-3-trifluoromethyl-5-(iodo)pyridine I (greater than 80% yield). The 2-hydroxy-3-trifluoromethyl-5-(iodo)pyridine I is then mixed with POCl3 in DMF and heated to 130 C. in a microwave for 20 minutes to produce 2-chloro-3-trifluoromethyl-5-(iodo)pyridine J (yield of 50 to 55%). The 2-chloro-3-trifluoromethyl-5-(iodo)pyridine K is reacted in a solution of pMBnNH2, palladium(II) acetate, 2,2?-bis(diphenylphosphino)-1,1?-binaphthyl (BINAP), triethylamine, and cesium carbonate in toluene to produce 5-((4-methoxyphenyl))methylamino)-2-chloro-3-(trifluoromethyl)pyridine K (yield of 40%). The 5-((4-methoxyphenyl))methylamino)-2-chloro-3-(trifluoromethyl)pyridine K is reacted in a solution of zinc cyanide, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), and 1,1?-bis(diphenylphosphino)ferrocene (dppf) in DMF to provide 5-(4-methoxybenzylamine)-2-cyano-3-(trifluoromethyl)pyridine K (yield of 92%). The 5-(4-methoxybenzylamine)-2-cyano-3-(trifluoromethyl)pyridine K is reacted in a solution of dichloromethane and trifluoroacetic acid to provide 2-cyano-3-trifluoromethyl-5-(amino)pyridine H (yield greater than 95%). The 2-cyano-3-trifluoromethyl-5-(amino)pyridine H is reacted with thiophosgene in water at 25 C. for 2 hours to provide 5-isothiocyanato-3-(trifluoromethyl)pyridine-2-carbonitrile A (yield of 74% to 95%).

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, 887707-23-5, 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; Jung, Michael E.; Sawyers, Charles L.; Ouk, Samedy; Tran, Chris; Wongvipat, John; (28 pag.)US9388159; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 211308-81-5, 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 211308-81-5 as follows.

Preparation 5 : 5-Chloro-l/T-pyrrolo[2,3-b]pyridine-2-carboxylic acid; Pyruvic acid (0.43ml, 6.24mmol) was added to a solution of 5-chloro-3-iodopyridin-2-ylamine (Preparation 4, 500mg, 2.08mmol), palladium acetate (23mg, O.lOmmol) and DABCO (700mg, 6.24mmol) in anhydrous DMF (2OmL). The reaction mixture was degassed with argon for 20min, then heated to HO0C for 16h. The solvent was removed in vacuo and the residue suspended in water (1OmL) and acetic acid (5mL) and then filtered. The solid was dissolved in EtOAc (5OmL), extracted into 2N NaOH solution (5OmL) and the organic layer discarded. The aqueous solution was acidified with concentrated HCl and extracted into EtOAc (2x40mL). The combined organics were dried (MgSO4) and concentrated in vacuo to give the title compound as a beige solid. deltaH (CD3OD): 7.14 (IH, s), 8.14 (IH, d), 8.35 (IH, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,211308-81-5, its application will become more common.

Reference:
Patent; PROSIDION LIMITED; WO2006/59164; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 228410-90-0 ,Some common heterocyclic compound, 228410-90-0, molecular formula is C6H5BrN2O3, 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 solution of 5-bromo-4-methyl-3-nitropyridin-2-ol (24 g, 103 rnmol) in DMF (200 ml) was added K2CO3 (21.39 g, 155 mmol) and CH3I (21.86 g, 155 mmol). The reaction mixture was stirred at room temperature for 2h. The reaction mixture was poured into ice cold water, the solid formed was filtered and dried under vacuum to afford title compound as off white solid (23.5 g, 92 %). FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, DMSO-d6) delta 8.40 (s, 1H), 3.51 (s, 3H), 2.21 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,228410-90-0, its application will become more common.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BORUAH, Anima; CHITTY VENKATA, Srikanth; HOSAHALLI, Subramanya; PANIGRAHI, Sunil Kumar; WO2014/125408; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 15862-50-7, Adding some certain compound to certain chemical reactions, such as: 15862-50-7, name is 3-Bromo-2-methoxy-5-nitropyridine,molecular formula is C6H5BrN2O3, 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 15862-50-7.

Step 1) A mixture of 3-bromo-2-methoxy-5-nitropyridine (Intermediate 51, 25 g, 107.3 mmol), tributyl(l-ethoxyvinyl)stannane (43.5 mL, 130.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (8.68 g, 7.51 mmol) in anhydrous DMAC (100 mL) was purged with N2 for 30 min and then heated at 120C for 3 h. After cooling to rt the mixture was poured into 1M aqueous HC1 (500 mL). The mixture was stirred overnight before saturated aqueous potassium sodium tartrate solution (800 mL) was added and the mixture was extracted with EtOAc (2 x 300 mL). The combined organic phases were dried (MgS04), filtered and concentrated in vacuo. Purification by gradient flash column chromatography eluting with 0-30% EtOAc in z’sohexane yielded a yellow solid, which was slurried in diethyl ether and filtered to afford l-(2-methoxy-5-nitropyridin-3-yl)ethanone (3.38 g, 17.2 mmol) as white solid. LCMS (Method 3): m/z 197 (ES+), at 1.09 min. (0387) 1H NMR: (400 MHz, DMSO-i) delta: 2.62 (s, 3H), 4.13 (s, 3H), 8.66 (d, J=2.8, 1H), 9.24 (d, J=2.8, 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. 15862-50-7, 3-Bromo-2-methoxy-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HEPTARES THERAPEUTICS LIMITED; CHRISTOPHER, John Andrew; BUCKNELL, Sarah Joanne; CONGREVE, Miles Stuart; TEHAN, Benjamin Gerald; NONOO, Rebecca Helen; BROWN, Giles Albert; SWAIN, Nigel Alan; MILLS, Mark; (111 pag.)WO2019/86902; (2019); A1;,
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. 128071-77-2, name is 4-Bromo-2-fluoronicotinaldehyde, molecular formula is C6H3BrFNO, 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: C6H3BrFNO

A mixture of 4-bromo-2-fluoro- pyridine-3-carbaldehyde (2.04 g, 10.0 mmol, 1.0 eq.), methylhydrazine (1.05 mL, 20.0 mmol, 2.0 eq.) and DIEA (3.48 mL, 20.0 mmol, 2.0 eq.) in MeCN (50 mL, 0.2 M) was stirred at 50 C. After 1 h, the mixture was diluted with EtOAc and washed with water (2x). The aqueous layer was extracted with EtOAc (3x). The combined extracts were washed with brine, dried over Na2S04, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel (0-60% EtOAc/hexanes) afforded the title compound as a white crystalline solid (1.73 g, 82%). XH NMR (400 MHz, CDCI3) delta 8.36 (d, J= 4.9 Hz, 1H), 8.04 (s, 1H), 7.33 (d, J = 4.9 Hz, 1H), 4.18 (s, 3H); ES-MS [M+l]+: 214.2.

With the rapid development of chemical substances, we look forward to future research findings about 128071-77-2.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig W.; CONN, P., Jeffrey; BOLLINGER, Katrina A.; ENGERS, Darren W.; BLOBAUM, Anna L.; ENGERS, Julie L.; ROOK, Jerri M.; (96 pag.)WO2018/63552; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 727356-19-6, 2-Bromo-6-(chloromethyl)pyridine, 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, name: 2-Bromo-6-(chloromethyl)pyridine, blongs to pyridine-derivatives compound. name: 2-Bromo-6-(chloromethyl)pyridine

A214.1a (133 mmol) was dissolved in DMF (250 niL) and potassium phthalimide (54.2 g, 293 mmol) was added portionwise to maintain the internal temperature below 3O0C. An additional portion of DMF (50 mL) was used to rinse the flask and powder funnel used for the potassium phthalimide addition. The reaction was stirred at room temperature overnight after which the reaction was judged complete by HPLC analysis. Water (600 mL) was added slowly to the reaction and after 30 minutes of stirring the resulting precipitate was collected by filtration, washed with several portions of water (1000 mL total) and allowed to air dry. The resulting solid, which contained the desired product along with excess phthalimide, was resuspended in water (700 mL) and the solution was made basic by addition of 1 N NaOH (3 mL). After slurrying for 20 minutes the solids were collected by filtration, washed with several portions of water and allowed to air dry. The solid still contained some phthalimide so was resuspended in MeOH (50 mL) and water (800 mL) and allowed to stir vigorously for 2 days. The solid was again collected by filtration, then slurried in hot MeOH (200-300 mL), cooled to room temperature and filtered. The solid was air dried to afford the phthalimide adduct, A214.1, along with residual phthalimide as a white solid. This material was used without further purification for the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,727356-19-6, 2-Bromo-6-(chloromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 60010-03-9, Adding some certain compound to certain chemical reactions, such as: 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine,molecular formula is C6H4Cl2N2O2, 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 60010-03-9.

6-Chloro-4-methyl-3-nitro-2-pyrrolidin-1 -yl-pyridine (Intermediate compound)To a solution of crude 2,6-dichloro-4-methyl-3-nitro-pyridine (see previous reaction; 23.87g; 115mmol), pyrrolidine (11 ml 1.1 eq) in 100 ml_ acetonitrile was added TEA (ca. 50 ml 3eq). After stirring overnight at room temperature one aliquot of water was added to the reaction mixture and the acetonitrile was removed in vacuo. The remaining aqueous layer was extracted with EtOAc (3x15OmL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to yield a dark semi-solid. The crude material was purified by flash column chromatography (5-40% EtOAc in heptane) to yield 1 Og (26% over three steps) of the title compound as a yellow solid.

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. 60010-03-9, 2,6-Dichloro-4-methyl-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROSEARCH A/S; BROWN, William, Dalby; JESSEN, Carsten; MATTSSON, Cecilia; SOTT, Richard; STRØBAeK, Dorte; WO2010/122064; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 103058-87-3 , The common heterocyclic compound, 103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde, 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.

n-Butyllithium (120 ml, 1.6M in hexane) is added to a suspension of 80.74 g of (3-methoxy- propyl)triphenylphosphonium bromide [11 1088-69-8] in 250 ml of tetrahydrofuran under an argon atmosphere at 0C. The reaction mixture is stirred at 0C for 50 minutes and then 28 g of 5-bromo-2-methoxypyridine-3-carbaldehyde [103058-87-3] are added. The reaction mixture is stirred at 0C for 1 hour and then at room temperature for 1 hour and diluted with tert-butyl methyl ether. The solution is washed with 1 M sodium bicarbonate solution. The organic phase is dried over sodium sulphate and evaporated. The title compound is obtained as a yellowish oil from the residue by flash chromatography (SiO2 60F). Rt = 5.03 (Gradient I)

The synthetic route of 103058-87-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2007/31558; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem