Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 17368-12-6, 2-Chloro-4-hydroxypyridine, 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

Tert-butyl 4-((2-chloropyridin-4-yl)oxy)piperidine-1-carboxylate (X22) To a solution of DEAD (97.4 mg, 0.56 mmol, 1.5 eq.) and PPh3 (146.6 mg, 0.56 mmol, 1.5 eq.) in THE (4 mL) at room temperature was added 1-Boc-4-hydroxypiperidine (75 mg, 0.37 mmol, 1.0 eq.). After 10 min, 2-chloro-4-hydroxypyridine (72.4 mg, 0.56 mmol, 1.5 eq.) was added and the reaction was heated to 50 C. The reaction was monitored via LCMS and after 12 h, the reaction was filtered through a syringe filter. The solvent was removed under vacuum. The crude residue was dissolved in DMSO (3 mL) and purified by Gilson HPLC (30*100 mm, 40-100% MeCN/H2O w/ 0.1% TFA). The desired fractions were concentrated to afford tert-butyl 4-((2-chloropyridin-4-yl)oxy)piperidine-1-carboxylate. ES-MS [M+1]+: 313.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17368-12-6, 2-Chloro-4-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Vanderbilt University; Lindsley, Craig W.; Conn, P. Jeffrey; Engers, Darren W.; Bollinger, Sean; Tarr, James C.; Spearing, Paul; Engers, Julie L.; Long, Madeline; Bridges, Thomas M.; (151 pag.)US2017/369505; (2017); 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. 884495-03-8, name is 3-Amino-2-bromo-5-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 3-Amino-2-bromo-5-fluoropyridine

Synthesis of Methyl 3-amino-5-fluoropicolinate[00148] To a steel bomb reactor, 2-bromo-5-fluoropyridin-3 -amine (1.0 equiv.), triethylamine (1.6 equiv.), Pd(BINAP)Cl2 (0.0015 equiv.) and anhydrous methanol (0.4 M solution) were added. After degassed by nitrogen stream for 15 min, the steel bomb reactor was closed and filled with CO gas up to 60 psi. The reactor was then heated to 100 C. After 3 h, more Pd catalyst (0.0015 equiv.) was added and the reaction mixture was re-heated to the same temperature for 3 h. After cooling down to room temperature, a brown precipitate was filtered off and the filtrate was extracted with EtOAc, which was washed with water and brine, dried over anhydrous sodium sulfate, and filtered. After removing volatile materials, the crude yellow product was obtained and used for the next step without further purification (40%). LCMS (m/z): 271.2 (MH+); LC R, = 3.56 min.

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, 884495-03-8, 3-Amino-2-bromo-5-fluoropyridine.

Reference:
Patent; NOVARTIS AG; BURGER, Matthew; DING, Yu; HAN, Wooseok; LINDVALL, Mika; NISHIGUCHI, Gisele A.; RICO, Alice; SMITH, Aaron; TANNER, Huw; WAN, Lifeng; WO2012/4217; (2012); 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. 5349-17-7, name is 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide

[0332] 7V-(3-Fluorophenyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (121). Reaction of bromoketone hydrobromide 1 (0.65 g, 2.3 mmol) and 3-fluorophenylthiourea (120) (0.39 g, 2.3 mmol) gave amine 121 (0.45 g, 71%) as a white powder: mp (EtOAc/pet. ether) 229-230 0C; 1H NMR delta 10.59 (br s, 1 H, NH), 8.63 (dd, J = 4.5, 1.6 Hz, 2 H, H-2′, H-6′), 7.35 (dd, J= 4.5, 1.6 Hz, 2 H, H-3′, H-5′), 7.28-7.31 (m, 1 H, H-2″), 7.76 (s, 1 H, H-5), 7.34-7.41 (m, 2 H, H-5″, H-6″), 6.77-6.84 (m, 1 H, H-4″); 13C NMR delta 163.0, 162.4 (d, J= 240 Hz), 150.1 (2), 147.6, 142.4 (d, J = 11 Hz), 140.8, 130.5 (d, J= 10 Hz), 119.8 (2), 112.7 (d, J= 2 Hz), 108.0, 107.5 (d, J= 21 Hz), 103.5 (d, J= 26 Hz). Anal, calcd for Ci4Hi0FN3S: C, 61.98; H, 3.72; N, 15.49. Found: C, 61.91; H, 3.79; N, 15.20%.

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, 5349-17-7, 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLAND UNISERVICES LIMITED; WO2009/114552; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 676371-00-9 ,Some common heterocyclic compound, 676371-00-9, molecular formula is C7H6BrN3, 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 8.00 g (100 mmol) freshly prepared difluoroacetaldehyde in 560 mL DCM was added 5.30 g (25 mmol) 6-bromoimidazo[1 ,2-a]pyridin-8-amine, 26.49 g (125 mmol) sodium triacetoxy borohydride and 28.5 g (18.56 mL, 250 mmol) TFA and the mixture was stirred for 72 h at rt to give, after working up andpurification, 4.0 g (58 ?) of the title compound. UPLC MS: RT = 0.71 min; m/z (ES+) 277.1 [MH+]; required MW = 276.1. 1 H-NMR (300 MHz ,DMSO-d6), delta [ppm]= 3.69 (2H), 6.36 (1 H), 6.54 (1 H), 7.41 (1 H), 7.77 (1 H), 8.10 (1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,676371-00-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; WENGNER, Antje; NEUHAUS, Roland; SIEMEISTER, Gerhard; WO2012/136531; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 65938-77-4, 5-Methyl-2-pyridinesulfonamide, 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, Product Details of 65938-77-4, blongs to pyridine-derivatives compound. Product Details of 65938-77-4

To a mixture of 5-methylpyridine-2-sulfonamide (109 mg, 0.63 mmol) in 1 M aqueous NaOH (0.63 mL, 0.63 mmol) was added tert-butyl hypochlorite (86 uL, 0.76 mmol) and the reaction stirred at room temperature for 1 .5h in the dark. The reaction was evaporated and the desired product washed with diethyl ether and dried under reducedpressure to yield the crude product. Used in the next step without further purification. It was assumed that the reaction gave quantitative yield. LCMS m/z 207 [M+H] – Na.

The synthetic route of 65938-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLACTONE PHARMA DEVELOPMENT AB; JOHANSSON, Martin; STERNER, Olov; (84 pag.)WO2018/104295; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 168823-76-5, 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. 168823-76-5, name is 5-Bromo-2-(chloromethyl)pyridine. A new synthetic method of this compound is introduced below.

Example A50 Preparation of intermediate 50: (5-Bromo-pyridin-2-yl)-acetonitrile Potassium cyanide (0.489 g, 7.41 mmol) and potassium iodide (0.013 g, 0.079 mmol) were added to a stirred solution of 5-bromo-2-chloromethyl-pyridine (0.9 g, 3.70 mmol) (obtained by procedures similar to those described in, van den Heuvel, M. et al.; J. Org. Chem., 2004, 250) in a mixture of ethanol (6 ml) and water (2 ml). The mixture was stirred at 80 C. for 6 h., then diluted with dichloromethane and washed with a saturated solution of sodium hydrogen carbonate. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; dichloromethane). The desired fractions were collected and concentrated in vacuo to yield intermediate 50 (0.498 g, 68%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,168823-76-5, 5-Bromo-2-(chloromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Pastor-Fernandez, Joaquin; Bartolome-Nebreda, Jose Manuel; Macdonald, Gregor James; Conde-Ceide, Susana; Delgado-Gonzalez, Oscar; Vanhoof, Greta Constantia Peter; Van Gool, Michiel Luc Maria; Martin-Martin, Maria Luz; Alonso-de Diego, Sergio-Alvar; Swinney, Kelly Ann; Leys, Carina; Weerts, Johan Erwin Edmond; Wuyts, Stijn; US2011/269752; (2011); 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. 944401-56-3, name is 5-Bromo-4-(trifluoromethyl)pyridin-2-amine. A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-4-(trifluoromethyl)pyridin-2-amine

Example 9: Preparation of 5-(1 -ethoxyvinyl)-4-(trifluoromethyl)pyridin-2 -amine Bis(triphenylphosphine)palladium(ll)dichloride (0.74g, 1.0373 mmol) and 5-bromo-4- (trifluoromethyl)pyridin-2-amine ( 5 g, 20.75mmol) were stirred in dimethylformamide(10 mL) under nitrogen and the tributyl(1-ethoxyvinyl)stannane (7.5g, 20.75 mmol) was added. The mixture was heated to 80C for 2h, then to 100 degrees for a further 2h). The mixture was poured into saturated brine (250 mL) and was extracted with three portions of dichloromethane. The extracts were dried over anhydrous magnesium sulphate, and the solution was evaporated, giving an orange oil (4.0g, 83%) H NMR (CDCI3) 8.19(s, 1 H); 6.70(s, 1 H); 4.77(bs, 2H); 4.28(d,1 H); 4.23(d, 1 H); 3.86(q, 2H); 1.35(t,3H).

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, 944401-56-3, 5-Bromo-4-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; CLOUGH, John Martin; BOEHMER, Jutta Elisabeth; PHADTE, Mangala; SONAWANE, Ravindra; LONGSTAFF, Adrian; MORRIS, James Alan; DESSON, Timothy Robert; HOTSON, Matthew Brian; RUSSELL, Sally; LING, Kenneth; BARNETT, Susan Patricia; BACON, David Philip; MOSELEY, Donn Warwick; MOUND, William Roderick; DOWLING, Alan John; WO2015/18432; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 552331-00-7 , The common heterocyclic compound, 552331-00-7, name is 4-Iodopyridin-2-amine, molecular formula is C5H5IN2, 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 (3S)-cyclopropyl-2-oxopyrrolidine-3-carbonitrile obtained in Step D of Example 1 (5.4 g), 4-iodopyridin-2-amine (7.2 g), N,N’-dimethylethane-1,2-diamine (1.5 mL), potassium carbonate (9.0 g) and copper(I) iodide (2.5 g) in 1,2-dimethoxyethane (60 mL) was stirred in a microwave reactor at 130 C. for 1 hr. The insoluble substance was removed through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) to give the title compound (7.7 g). 1H NMR (400 MHz, DMSO-d6) delta0.46-0.55 (2H, m), 0.57-0.63 (1H, m), 0.64-0.72 (1H, m), 1.44-1.54 (1H, m), 2.27-2.37 (1H, m), 2.56-2.67 (1H, m), 3.81-3.91 (2H, m), 6.01 (2H, s), 6.74-6.84 (2H, m), 7.80-7.92 (1H, m). MS(ESI+): [M+H]+ 243.1.

The synthetic route of 552331-00-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Saitoh, Morihisa; Yogo, Takatoshi; Kamei, Taku; Tokunaga, Norihito; Ohba, Yusuke; Yukawa, Takafumi; (191 pag.)US2016/159773; (2016); 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. 848139-78-6, name is 6-Amino-4-((3-chloro-4-(pyridin-2-ylmethoxy)phenyl)amino)-7-ethoxyquinoline-3-carbonitrile, molecular formula is C24H20ClN5O2, 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. Safety of 6-Amino-4-((3-chloro-4-(pyridin-2-ylmethoxy)phenyl)amino)-7-ethoxyquinoline-3-carbonitrile

Example 2: Process 24-Dimethylaminocrotonoyl chloride hydrochloride and its coupling with 6-amino-4-(3-chloro-4-(pyridin-2-ylmethoxy)phenylamino)-7-ethoxyquinoline-3-carbonitrile (procedure with phosphorus oxychloride and DMAc). A suspension of 4-dimethylaminocrotonic acid (6.70 kg, 40.4 mol) in DMAc (64.3 kg) was cooled to -14 to -19 0C. Neat POCI3 (6.15 kg, 40.1 mol) was added to the slurry at a rate to maintain the temperature in the reactor in the above range (moderate exotherm). The reaction mixture was held at -15 0C for 2-3 hrs. Conversion of the acid to acid chloride was monitored by HPLC: an aliquot of the reaction mixture was quenched into anhydrous ethanol and the solution was analyzed by HPLC using SIELC Primesep 200 column capable of retaining polar compounds. The conversion was calculated as a ratio of peak areas corresponding to the starting acid and its ethyl ester formed by reaction of the acid chloride with ethanol. After conversion reached the maximum (usually 85 to 95% after 2 to 3 hours), a solution of the aminoquinoline (12.6 kg, 28.3 mol) in DMAc (99.4 kg) was added to the reactor maintaining the temperature in the -14 to -19 0C range. Resulting mixture was held for 5 hr at approximately – 15 0C. At this point HPLC analysis showed residual aniline level at or below 0.5%. The thick suspension of the hydrochloride salt of the coupled product was quenched with water (87.1 kg) maintaining the batch temperature between -7 to -16 0C. The resulting clear solution in was warmed to 37-42 0C and its pH was adjusted to 10-1 1 with a 25% aqueous solution of KOH (approx. 53 kg of the solution was added). The suspension was further diluted with water (95 kg) and the solids were filtered on a polypropylene cloth filter. The cake was washed with water until neutral pH of the washes and dried first in the nitrogen flow on the filter and then on trays in vacuum at 45 to 50 0C to afford crude (E)-Lambda/-(4-(3-chloro-4-(pyridin-2-ylmethoxy)phenylamino)- 3-cyano-7-ethoxyquinolin6-yl)-4-(dimethylamino)but-2-enamide (15.75 kg, 94%) as a bright- yellow crystalline solid.

With the rapid development of chemical substances, we look forward to future research findings about 848139-78-6.

Reference:
Patent; WYETH LLC; GONTCHAROV, Alexander; ENG, Kan Kaung; SUTHERLAND, Karen; SEBASTIAN, Alice; YU, Qing; PLACE, David William; WO2010/48477; (2010); A2;,
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. 955370-07-7, name is 2-(6-Bromopyridin-2-yl)ethanol, molecular formula is C7H8BrNO, 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. Product Details of 955370-07-7

Step HThe title compound from Step G above (5 g, 24.75 mmol) was dissolved in N,N’-dimethylformamide (100 mL) and imidazole (4.84 g, 74.25 mmol) was added. After the addition of chlorotriisopropylsilane (7.92 mL, 37.1 mmol), the mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with diethylether (300 mL) and washed with a 10% citric acid solution (3¡Á40 mL) and brine (100 mL). The organic phase was separated, dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using ethylacetate/n-heptane (5/95) to afford the title compound as a colorless liquid (7.36 g, 83%).1H-NMR (400 MHz, CDCl3): d=0.92-1.13 (m, 21H), 3.00 (t, 2H), 4.08 (q, 2H), 7.22 (d, 1H), 7.33 (d, 1H), 7.45 (t, 1H)

With the rapid development of chemical substances, we look forward to future research findings about 955370-07-7.

Reference:
Patent; AC Immune S.A.; US2011/92537; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem