Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 878197-68-3, 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde, 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: C8H5BrN2O, blongs to pyridine-derivatives compound. Formula: C8H5BrN2O

The reactor is charged with N-methylpiperazine (3.1 Kg, 31 mol ) and tetrahydrofuran (10 Liters) and stirred under nitrogen while cooling to negative 20 0C. n-Butyl lithium (10.4 L, 26.0 mol) is added to the reaction at a rate to maintain the negative 20 0C temp and the contents are stirred for 15 to 30 minutes. A slurry of 5- bromoimidazo[1 ,2-a]pyridine-2-carbaldehyde (2.79 Kg, 12.4 mol) in tetrahydrofuran (10 Liters) is added at a rate to maintain the reaction at ?0C. The slurry is washed in with additional tetrahydrofuran (6 Liters). The reaction is stirred for 30 minutes and warmed to approximately negative 10 0C. The reaction is quenched by addition of 6N HCI solution to achieve pH 4.0 while maintaining at ? 150C. The reaction is diluted with heptane (14 Liters) and the layers allowed to separate. The lower aqueous layer is drained and the upper organic layer is washed with 1 N HCI (2 x 1.5 Liters). The combined aqueous layers are stirred at 20 degrees and adjusted to pH 9 with 4N NaOH solution. The Aqueous layer is extracted with 10% iPrOH/CH2CI2 (3 x 28 Liters) and the combined organic layers are washed with saturated NaHCO3 solution (14 Liters) and evaporated at <25 0C to approximately 3 volumes, lsopropanol (28 Liters) is added and reaction again concentrated under reduced pressure to approximately 8.5 Liters, lsopropanol (17 Liters) is added and the reaction is treated with a solution of oxalic acid (1.0 Kg, 11.1 mol) in isopropanol (7 Liters) at a rate to maintain good stirring and temperature between approximately 25-4O0C. The reaction is stirred for 30 minutes and the solids are collected and washed with isopropanol (8.5 Liters) Solids are dried at 50 0C to yield 5-(4-methyM- piperazinyl)imidazo[1 ,2-a]pyridine-2-carbaldehyde, (2.25 Kg, 54% yield) 1 H NMR (400 MHz, DMSO-D6) delta ppm 10.01 (s, 1 H) 8.47 (s, 1 H) 7.41 (m, 2 H) 6.65 (m, 1 H) 3.34 (s, 8 H) 2.78 (s, 3 H) At the same time, in my other blogs, there are other synthetic methods of this type of compound,878197-68-3, 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde, and friends who are interested can also refer to it. Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/26703; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 167837-43-6 , The common heterocyclic compound, 167837-43-6, name is (E)-3-(6-Aminopyridin-3-yl)acrylic acid, molecular formula is C8H8N2O2, 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.

EDC (231 mg, 1.2 mmol) was added to a solution of (E)-3- (6-amino-pyridin-3- yl) acrylic acid (164 mg, 1.0 mmol), (2-propoxy-3-methoxy-benzyl) methylamine (230 mg, 1.1 mmol), HOBT’H20 (149 mg, 1.1 mmol) and DIPEA (525 L) L, 3.0 mmol) in dry DMF (10 mL). After 18 hr of stirring, the mixture was diluted with water (60 mL) and extracted with EtOAc (2X20 mL). The organic layer was washed with brine (2X30 mL), dried and evaporated. Flash chromatography (silica 1-3% MEOH in CH2CL2) furnished pure free base which was dissolved in CHZCLZ (10 mL). After addition of HCl (1.5 mL, 1M in ether), the solvents were evaporated; the residue was washed with ether and dried to afford the title compound (185 mg, 47%). 1H NMR (300 MHz, DMSO-d6) 8 8.16 (m, 3H), 7.48 and 7.45 (rotamers, 2d, J= 15.4 Hz, 1H), 7.23 (d, J= 15. 4 Hz, 1H), 7.00 (m, 3H), 6.61 (m, 1H), 4.78 and 4.63 (rotamers, 2s, 2H), 3.87 (m, 2H), 3.79 (s, 3H), 3.09 and 2.85 (rotamers, 2s, 3H), 1.71 (m, 2H), 0.97 (m, 3H). MS (ESI) M/E 356 (M+H) +.

The synthetic route of 167837-43-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2004/52890; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1060814-91-6, Ethyl 2-(4-bromopyridin-2-yl)acetate, 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: C9H10BrNO2, blongs to pyridine-derivatives compound. Formula: C9H10BrNO2

To a solution of compound 6-7 (2.5 g, 10.24 mmol, 1 eq) and compound 6-10 (2.6 g, 10.24 mmol, 1 eq) in dioxane (40 mL) was added potassium acetate (3.02 g, 30.73 mmol, 3 eq) and Pd(dppf)Cl2.CH2Cl2 (418 mg, 512.12 umol, 0.05 eq). The mixture was degassed under vacuum and purged with nitrogen for three times. The mixture was stirred at 85C for 2 hours under nitrogen atmosphere. TLC (petroleum ether: ether: ethyl acetate = 2:1) showed the starting material was consumed completely and a new spot was formed. The mixture was used directly without work up.

The synthetic route of 1060814-91-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; TRI-INSTITUTIONAL THERAPEUTICS DISCOVERY INSTITUTE, INC.; FUSHIMI, Makoto; SCALTRITI, Maurizio; HELLER, Daniel, Alan; MONTERRUBIO MARTINEZ, Carles; ARRUABARRENA ARISTORENA, Amaia; MEINKE, Peter, T.; FOLEY, Michael, Andrew; ASANO, Yasutomi; ASO, Kazuyoshi; TAKAHAGI, Hiroki; SHAMAY, Yosef; BASELGA TORRES, Jose, Manuel; SASAKI, Yusuke; MICHINO, Mayako; (271 pag.)WO2020/72892; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1122-43-6 ,Some common heterocyclic compound, 1122-43-6, molecular formula is C7H9NO, 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.

Description 143-(2-Fluoro-4-nitrophenoxy)- 14)2,6-Dimethyl-pyridin-3-ol (3.0 g, 24.35 mmol) and cesium carbonate (15.87 g, 48.71 mmol) were added to a solution of 3,4-difluoronitrobenzene (3.87 g, 24.35 mmol) in DMF (30 ml). The mixture was heated at 140 0C for 2 hours. After cooling to room temperature it was filtered through diatomaceous earth and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; 2 % methanol/DCM as eluent) to yield intermediate D14 (5.88 g, 92 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-43-6, its application will become more common.

Reference:
Patent; ORTHO-McNEIL-JANSSEN PHARMACEUTICALS, INC.; ADDEX PHARMA S.A.; WO2009/33702; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 850663-54-6, 4-Chloro-5-nitropyridin-2(1H)-one, 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, COA of Formula: C5H3ClN2O3, blongs to pyridine-derivatives compound. COA of Formula: C5H3ClN2O3

(4c) 4-chloro-2-methoxy-5-nitropyridine 4-Chloro-5-nitropyridin-2-ol (1.18 g, 6.76 mmol) produced in Example 4 (4b) was suspended in tetrahydrofuran (15 mL) and, silver carbonate (2.80 g, 10.1 mmol) and methyl iodide (2.10 ml, 33.8 mmol) were added at room temperature, and the mixture was stirred at the same temperature for 13 hr. The insoluble material was filtered off with celite, and the filtrate was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform). The solvent of the object fraction was evaporated under reduced pressure to give the title object compound as a pale-yellow powder (730 mg, yield 57%). 1H-NMR (CDCl3, 400 MHz) delta: 4.03 (3H, s), 6.90 (1H, s), 8.88 (1H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,850663-54-6, 4-Chloro-5-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Kyoto Pharmaceutical Industries, Ltd.; SHIRAHASE, Hiroaki; TAKAHASHI, Kenji; SHOJI, Yoshimichi; TAKEDA, Shigemitsu; (111 pag.)US2016/207883; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54453-93-9, Adding some certain compound to certain chemical reactions, such as: 54453-93-9, name is Ethyl 2-Chloropyridine-4-carboxylate,molecular formula is C8H8ClNO2, 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 54453-93-9.

2.04 g of sodium borohydride are added portionwise to a solution of 1.7 g of ethyl 2-chloropyridine-4-carboxylate in 20 ml of ethanol, under an inert atmosphere of argon at a temperature in the region of 0 C. The reaction mixture is refluxed with stirring for 3 hours and then concentrated to dryness under reduced pressure. The residue thus obtained is taken up in dichloromethane and then washed with water. The organic phase is dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure. 1 g of 2-chloro-4-(hydroxymethyl)pyridine is thus obtained.

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. 54453-93-9, Ethyl 2-Chloropyridine-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVENTIS PHARMA S.A.; US2004/248884; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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