Pyridine-derivatives

Electric Literature of 915107-31-2 ,Some common heterocyclic compound, 915107-31-2, molecular formula is C8H8ClNO3, 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.

3- (4- (Trifluoromethyl) phenyl) pyrrolidine (210 mg, 0.98 mmol) , methyl 6-chloro-5-methoxynicotinate (192 mg, 0.95 mmol) and K 2CO 3 (386 mg, 2.79 mmol) were dissolved in DMSO (6 mL) , and the mixture was heated to 100 and stirred for 5 h. The reaction mixture was cooled to room temperature, diluted with EtOAc (60 mL) , and washed with water (15 mL) and saturated aqueous NaCl (15 mL×5) successively, dried over anhydrous Na 2SO 4 , and concentrated in vacuo to give a crude product, which was purified by silica-gel column chromatography (eluent: PET/EtOAc (v/v) = 5/1) to give a light yellow solid (280 mg, 75%) . [0690] MS (ESI, pos. ion) m/z = 381.2 [M+1] +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,915107-31-2, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHONG, Xue; WANG, Feng; LI, Xuke; HE, Wei; PAN, Wei; HUANG, Jiuzhong; ZHANG, Yingjun; ZHENG, Changchun; (0 pag.)WO2020/11147; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53554-20-4, 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. 53554-20-4, name is 6-Amino-2-chloronicotinonitrile, molecular formula is C6H4ClN3, 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.

A mixture of NMP (8mL), I2 (82.6mg, 0.33mmol), and Zn (809mg, 12.4mmol) was stirred at rt until the red colour of I2 disappeared (ca. 4min). Butyl-1-bromide (0.88mL, 8.14mmol) was added and the mixture was stirred at 80C for 3h. The mixture was cooled to rt and 38 (1.00g crude, max. 4.30mmol) and Pd2(PPh3)4 (150mg, 0.13mmol) were added, and the reaction mixture was stirred at rt for 1h. Sat. aq. NH4Cl (120mL) was added, and the mixture was extracted with EtOAc (2×120mL). The combined organic phase was washed with brine (120mL), dried over Mg2SO4, and evaporated under vacuum. Purification by FC (heptane/EtOAc 100:0 to 0:100) afforded the product with small impurities as light yellow solid (225mg, 29% over 2 steps). 1H NMR (CDCl3) delta 7.56 (d, J=8.5Hz, 1H), 6.35 (d, J=8.5Hz, 1H), 5.00 (b s, 2H), 2.83 (t, J=8.8Hz, 2H), 1.66-1.79 (m, 2H), 1.43 (sxt, J=7.3Hz, 2H), 1.20-1.35 (m, 3H, impurity), 0.97 (t, J=7.3Hz, 3H), 0.90 (t, J=6.7Hz, 2H, impurity). 13C NMR (CDCl3) delta 166.3, 159.7, 141.1, 135.1 (impurity), 127.6 (impurity), 118.5, 105.5, 96.6, 36.7, 31.8 (impurity), 31.4, 29.0 (impurity), 22.6 (impurity), 22.4, 14.1 (impurity), 13.8.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 53554-20-4, 6-Amino-2-chloronicotinonitrile.

Reference:
Article; Petersen, Jette G.; S°rensen, Troels; Damgaard, Maria; Nielsen, Birgitte; Jensen, Anders A.; Balle, Thomas; Bergmann, Rikke; Fr°lund, Bente; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 404 – 416;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55899-13-3 ,Some common heterocyclic compound, 55899-13-3, molecular formula is C14H17BrN2O3S, 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.

The reaction was performed using general flow procedure reacting 3-bromopyridine 2a with ethylpropiolate 4b. The outlet solution (195 mL, collected over 51 mins) was stirred at room temperature whiletriethylamine (17.5 mL, 126 mmol) was added followed by ethyl propiolate (9.30 mL, 98.4 mmol). The bright redmixture was stirred at room temperature for 15 minutes was concentrated in vacuo to remove the MeCN and thendiluted with EtOAc (250 mL) and brine (100 mL). The organic layer was separated and the aqueous phase washedtwice more with EtOAc (2 x 200 mL). The combined organic layers were dried over anhydrous sodium sulfate andconcentrated in vacuo to give a dark red oil.The crude material was purified by column chromatography on a 100 g silica column using the Biotage machine anda gradient from 7 to 60 % EtOAc/heptane. 5c eluted first from the column. Pale red solid (1.94 g, 51 min collectiontime, 11 %). 1H NMR (400 MHz, d6-DMSO) (3H, t, J = 4 Hz, CH2CH3), 4.31 (2H, q, J = 4 Hz, CH2CH3), 7.743 SYNLETT: LETTERTemplate for SYNLETT and SYNTHESIS Thieme Stuttgart · New York 2017-04-25 page 3 of 4(1H, d, J = 8 Hz, ArH), 8.01 (1H, d, J = 4 Hz, ArH), 8.47 (1H, s, ArH), 9.31 (1H, s, ArH) ppm. 13C NMR (101 MHz,d6-DMSO) 14.3, 59.8, 103.6, 108.1, 118.9, 130.3, 131.3, 138.6, 144.7, 162.2 ppm. HRMS (FAB) calcd forC10H10O2N2Br 268.99202, found 268.99194/270.98981

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. 55899-13-3, 1-Amino-3-bromopyridin-1-ium 2,4,6-trimethylbenzenesulfonate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Brocklehurst, Cara E.; Koch, Guido; Rothe-Poellet, Stephanie; La Vecchia, Luigi; Synlett; vol. 28; 13; (2017); p. 1636 – 1640;,
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. 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 3-Bromo-2-chloro-6-picoline

General procedure: Method A: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-fluoropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DMAP (2.5 mmol). The tube was purged with argon. Then DMF (10V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a preheated oil bath at 120 0C for 8 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone. Method B: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-chloropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DBU (2.5 mmol). The tube was purged with argon. Then DMF (10 V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a pre heated oil bath at 135 0C for 12 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone.

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, 185017-72-5, 3-Bromo-2-chloro-6-picoline.

Reference:
Article; Anchan, Kavitha; Baburajan, Poongavanam; Puttappa, Nagaswarupa H.; Kumar Sarkar, Sujit; Synthetic Communications; vol. 50; 3; (2020); p. 348 – 360;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1111637-74-1 ,Some common heterocyclic compound, 1111637-74-1, molecular formula is C7H5BrFNO, 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.

Preparation of (ii^-iV-il-iS-bromo-Z-fluoropyridin-S-y ethylideneJ-Z-methylpropane- 2-sulfinamide (25A). A mixture of l-(5-bromo-2-fluoropyridin-3-yl)ethanone (prepared according to procedures described in WO2009016460; 11.0 g, 50.5 mmol), (i?)-2-methylpropane-2- sulfinamide (AK Scientific, 12.2 g, 101 mmol) and titanium(IV) ethoxide (Aldrich, 26.1 mL, 126.0 mmol) in THF (100 mL) was heated at reflux for 2 hours. The mixture was cooled to room temperature, and brine (200 mL) was added. The suspension was vigorously stirred for 10 minutes. The suspension was then filtered through a pad of silica gel and the organic phase was separated. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SC>4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (gradient 0-20% EtOAc/hexanes) to afford (i?,Z)-N-(l-(5-bromo-2-fluoropyridin-3-yl)ethylidene)-2-methylpropane-2-sulfinamide (25A) as a bright yellow oil ( 16 g, 99% yield). MS m/z = 320.8 (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,1111637-74-1, its application will become more common.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BOURBEAU, Matthew, P.; BROWN, James, A.; CHEN, Ning; FROHN, Michael, J.; LIU, Longbin; LIU, Qingyian; PETTUS, Liping, H.; QIAN, Wenyuan; REEVES, Corey, M.; SIEGMUND, Aaron, C.; (509 pag.)WO2017/24180; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59290-81-2, 2-Methyl-5-nitro-3-pyridinecarboxylic 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, SDS of cas: 59290-81-2, blongs to pyridine-derivatives compound. SDS of cas: 59290-81-2

4-(Pyridin-2-ylmethoxy)-phenylamine (0.4 mmol), prepared as described for intermediate II, was coupled with 1 (72 mg, 0.4 mmol) in 4 ml DCM and 1 ml DMF in the presence of PyBOP (416 mg, 0.8 mmol) and DIEA (204 mul, 1.2 mmol). After stirring overnight at r.t, the reaction mixture was diluted with DCM, and washed with aq. NaHCO3. The DCM phase was concentrated, the residue was dissolved in DMF and then subjected to preparative HPLC purification. The target product (173 mg) was obtained as an off white solid. (Calculated mass: 364.3, observed mass: 364.5).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59290-81-2, 2-Methyl-5-nitro-3-pyridinecarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; KEMIA, INC.; WO2007/56016; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83664-33-9, Adding some certain compound to certain chemical reactions, such as: 83664-33-9, name is 2-(Benzyloxy)-5-bromopyridine,molecular formula is C12H10BrNO, 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 83664-33-9.

n-Butyl lithium (2. 5M, 95. 9 mmol, 38. 4 mL, 1. 05 eq.) was added dropwise via syringe to a stirred solution OF 2- (BENZYLOXY)-5-BROMOPYRIDINE (91. 3 mmol, 24. 1 G, 1. 0 eq.) in THF (260 mL, c = 0. 35) cooled to-78 C. Upon completion of addition, the solution was allowed to continue stirring at the same low temperature for 1 hour. At this point, NN-dimethylformamide (183 mmol, 13. 4 G, 2. 0 eq.) was added dropwise as a solution in 5 mL THF. Stirring was continued at the same low temperature for a further 30 minutes at which point the reaction was quenched by addition of 5% sodium bicarbonate. The mixture was transferred to a separatory funnel and extracted with ether (3 x 250 mL). The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant yellow oil was purified on a Biotage Sp4 65i over a gradient OF 0-50% hexanes in ethyl acetate to afford the title compound (14. 1 g, 73%). LRMS : 214 (M+H) +. ‘H NMR (DMSO-D6, 400 MHz) ; 10. 02 (1 H, s) 8. 86 (1 H, s) 8. 03 (1 H, d, J=9. 3 Hz) 7. 31-7. 43 (5 H, m) 6. 50 (1 H, d, J=9. 3 HZ) 5. 33 (2 H, s)

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. 83664-33-9, 2-(Benzyloxy)-5-bromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; WO2004/92145; (2004); 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. 72141-44-7, name is 4-Chloro-2-methoxypyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

To a solution of compound 2 (28.7 g. 0.2 mol) in DMF (50 mL) was added NBS (35.5 g, 0.2 mol). The mixture was heated at 90C for 8 hours. The crude compound 3 was collected by filtration. (22 g, 50% yield).

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, 72141-44-7, 4-Chloro-2-methoxypyridine.

Reference:
Patent; INTERMUNE, INC.; RAMPHAL, Johnnie, Y.; BUCKMAN, Brad, Owen; EMAYAN, Kumaraswamy; NICHOLAS, John, Beamond; SEIWERT, Scott, D.; WO2015/153683; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 61494-55-1, Adding some certain compound to certain chemical reactions, such as: 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid,molecular formula is C7H6ClNO2, 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 61494-55-1.

To a cooled solution of /V,7V-dicyclohexylcarbodiimide (7.36 g, 35.69 mmol, ) in dichloromethane (120 mL) was added DMAP (3.17 g, 25.96 mmol) at 0 C, followed by 2-(2- chloropyridin-3-yl)acetic acid (5.57 g, 32.45 mmol), and the resulting mixture was stirred at 0 C for 5 min. teri-Butanol (9.3 mL, 97.337 mmol) was then added to the reaction, and the resulting mixture was allowed to warm to room temperature with stirring for 12 h. The reaction was then evaporated to dryness to give a residue, which was dissolved in diethyl ether (400 mL). The ether solution was then filtered through a pad of celite, which was washed with diethyl ether (2 c 200 mL). The combined filtrates were washed sequentially with 1 M aqueous NaOH (300 mL), 2 N aqueous HC1 (300 mL), water (300 mL) and brine (200 mL). The organic layer was then dried over Na2S04, filtered and evaporated to dryness to give the crude product as a residue. Purification by flash column chromatography eluting with a gradient of ethyl acetate (5-20%) in hexane to afford the desired product as beige solid (5.25 g, 71.0%). UPLC-MS (Acidic Method, 2 min): rt = 1.08 min, m/z 228.1 [M+H]+. ‘H NMR (400 MHz, CDCb) d ppm 8.31 (dd, J=4.77Hz, 2.01Hz, 1H), 7.63 (dd, J=7.53Hz, 2.01Hz, 1H), 7.22 (dd, J=7.53Hz, 4.77Hz, 1H), 3.68 (s, 2H), 1.46 (s, 9H).

According to the analysis of related databases, 61494-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NFLECTION THERAPEUTICS, INC.; KINCAID, John; NEWSAM, John; KISAK, Edward; WOOTTON, Michael; KUSHWAHA, Avadhesh; (364 pag.)WO2020/106304; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 77199-09-8, 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 77199-09-8, name is Ethyl 5-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture 2a or 2b (1 g, 1 equiv.), anappropriate pinacol boronate ester (1.2 equiv.), [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex withdichloromethane (10 mol %), cesium carbonate (2.0 equiv.), 1,4-dioxane (8 ml) and water (4 ml) was sealed in a 20 ml microwavereaction vial (Biotage). The vial was irradiated in a microwaveapparatus at 110 C, normal absorption for 30-90 min. The reactionmixture was cooled to room temperature and work up was performedas described in method 1 to obtain the esters 4b-i.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 77199-09-8, Ethyl 5-bromopicolinate.

Reference:
Article; Tung, Truong Thanh; Jakobsen, Tim Holm; Dao, Trong Tuan; Fuglsang, Anja Thoe; Givskov, Michael; Christensen, S°ren Br°gger; Nielsen, John; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 1011 – 1020;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem