Tag: M.W:200-300

Electric Literature of 936011-17-5, 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 936011-17-5 as follows.

[0926] XXV-6 was obtained following the synthetic scheme as described above. MS (ESI) m/z (M+H)+ 231.95.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,936011-17-5, its application will become more common.

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Ramphal, Johnnie Y.; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/94456; (2014); 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. 1448427-99-3, name is 6-(4-Isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C10H13N5

Alternative Synthesis of Compound (A) Compound (E) (1 equiv.), Compound (C) (1 equiv.), DMF (about 16 vols), Et3N (1.5 equiv.), Pd(OAc)2(0.02 equiv.), and Ad2P(-Bu) (0.04 equiv.) were combined and the contents were purged with N2followed by CO and then pressurized with CO (20 psi). The reaction mixture was heated to about 95 C to about 105 C. After about 24 hours, the reaction was allowed to cool to about 20 C to about 30 C to afford Compound (A).

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, 1448427-99-3, 6-(4-Isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-amine.

Reference:
Patent; GILEAD SCIENCES, INC.; BROWN, Brandon Heath; CHAN, Brenda J. Burke; CHIU, Anna; GRIGGS, Nolan; HEUMANN, Lars V.; LATHROP, Stephen P.; REYNOLDS, Troy Evan; SARMA, Keshab; SILER, David Allen; THOMPSON, Andrew S.; WANG, Tao; (146 pag.)WO2016/106384; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1018505-59-3, 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.1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, molecular formula is C11H18N4, molecular weight is 206.2874, as common compound, the synthetic route is as follows.

Preparation of 6-chloro-N-(5-(4-ethylpiperazin-1-yl)pyridin-2-yl)imidazo[1,2-a]pyridin-8-amine A mixture of impure 5-(4-ethylpiperazin-1-yl)pyridin-2-amine (1.00 g, 4.85 mmol assumed), 8-bromo-6-chloroimidazo[1,2-a]pyridine hydrochloride salt (1.30 g, 4.85 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (634 mg, 1.02 mmol) and cesium carbonate (4.90 g, 15.0 mmol) in toluene (50 mL) was sparged with nitrogen while stirring for 10 min. Palladium(II) acetate (120 mg, 0.491 mmol) was then added and the reaction stirred at reflux for 18 h. After this time, the reaction was cooled to room temperature, diluted in a mixture of 1:1 methanol/methylene chloride (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, 1:19 methanol/methylene chloride to 1:6 methanol/methylene chloride) to afford 6-chloro-N-(5-(4-ethylpiperazin-1-yl)pyridin-2-yl)imidazo[1,2-a]pyridin-8-amine as a yellow-green solid: 1H NMR (400 MHz, DMSO-d6.) d 9.12 (s, 1H), 8.30 (d, J=2.0 Hz, 1H), 8.26 (d, J=2.0 Hz, 1H), 7.99 (d, J=2.8 Hz, 1H), 7.89 (d, J=0.8 Hz, 1H), 7.55 (d, J=0.8 Hz, 1H), 7.43 (dd, J=8.8, 2.8 Hz, 1H), 7.35 (d, J=8.8 Hz, 1H), 3.11-3.10 (m, 4H), 2.50-2.49 (m, 4H, merged with DMSO peak), 2.38-2.37 (m, 2H), 1.04 (t, J=7.2 Hz, 3H).

Statistics shows that 1018505-59-3 is playing an increasingly important role. we look forward to future research findings about 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine.

Reference:
Patent; Gilead Connecticut, Inc.; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Mitchell, Scott A.; Schmitt, Aaron C.; Xu, Jianjun; Zhao, Zhongdong; US2014/148430; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine, the common compound, a new synthetic route is introduced below. Product Details of 75806-86-9

Example 2: 2-Bromo-5-chloro-pyridin-3-ylamine; [00382] 2-Bromo-5-chloro-3-nitro-pyridine (11.87 g, 50 mmol) was dissolved in 100 mL ether. Tin(ll) chloride dihydrate (56.4g, 0.5 mol) was dissolved in 100 mL of concentrated hydrochloric acid and added drop wise over 15 minutes to the stirring ethereal solution of the nitro compound. The exothermic reaction brought the ether to boiling and it was allowed to evaporate off. After the addition was complete the reaction mixture was placed on a 50 C oil bath and stirred for 30 minutes to boil of the remaining ether. The flask was then cooled on in an ice bath. The precipitate formed was collected and by filtration and dissolved in 100 mL of water. The pH was adjusted to 9-10 by the addition of concentrated ammonium hydroxide solution and the product was extracted with ethyl acetate (2 x 100 mL). The organic layer was washed with diluted ammonium hydroxide, water and brine and dried over Na2SU4 and the solvent was evaporated to afford 7.4 g of tan crystalline solid. MS m/z : 208.9 (M+H).

The synthetic route of 75806-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 955372-86-8 ,Some common heterocyclic compound, 955372-86-8, molecular formula is C6H3BrFNO2, 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.

I ntermediate 7: 3-Bromo-5-( 2-ftuoro-phenylamino)-isonicotinic acid; Lithium bis(trimethylsilyl)amide (54.6 ml_, 1.0 M in THF, 54.6 mmol) was added to a solution of 2-fluoro aniline (3.5 mL, 36.4 mmol) in THF (100 ml_) at -78 0C. The resulting solution was for 1 h at -780C. S-Bromo-delta-fluoro-isonicotinic acid (1) (4.0 g, 18.2 mmol) was added as a solid, and the reaction solution was stirred for 48 h at room temperature. The reaction solution was concentrated via rotary evaporation; diluted with satd. NaHCO3, and washed with EtOAc. The aqueous solution was acidified with concentrated HCI. The resulting precipitate was filtered, washed with H2O, and dried under vacuum to afford the desired product (4.2 g, 74%) 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. 955372-86-8, 3-Bromo-5-fluoroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59105-50-9, (5-Bromopyridin-3-yl)(phenyl)methanone, 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: C12H8BrNO, blongs to pyridine-derivatives compound. Formula: C12H8BrNO

PdCl2(PPh3)2 (148 mg, 0.21 mmol) and CuI (120.6 mg, 0.63 mmol) were added to asolution of (5-bromopyridin-3-yl)(phenyl)methanone (1.1 g, 4.22 mmol) in Et3N (10 mL)under N2, and the resulting mixture was stirred for 30 min. Then ethynylbenzene (516 mg, 5.1mmol) was added dropwise and the reaction mixture was stirred overnight at roomtemperature, followed by filtration over Celite and evaporation under vacuum. Purificationby column chromatography on silica gel afforded the desired product.To the crude product in a mixture of THF (12 mL) and MeOH (12 mL) was added 10% Pdon carbon (80 mg), and the atmosphere was changed to H2 (2.5 bar). The resulting mixturewas stirred in a Parr hydrogenation apparatus overnight at room temperature, followed byfiltration over Celite and evaporation under vacuum. Purification by column chromatographyon silica gel afforded the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59105-50-9, (5-Bromopyridin-3-yl)(phenyl)methanone, and friends who are interested can also refer to it.

Reference:
Article; Fu, Yun; Sun, Jian; Molecules; vol. 24; 3; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1111637-94-5 , The common heterocyclic compound, 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, 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 solution of 19 (50 mg, 0.2369 mmol) and 2 (50 mg, 0.2369 mmol) in ethanol and toluene (1:4 mL) was added sodium carbonate (49.74 mg, 0.4738 mmol). The reaction was degassed and purged with nitrogen for 15 min. Pd(dppf)Cl2.DCM (9.06 mg, 0.0114 mmol), and again degassed for 15 min. The reaction mixture was stirred for 2 h at 90 C. and the reaction mixture allowed to cool to rt and diluted with DCM (25 mL). The organic layer was filtered through Celite and concentrated to get the crude. The resulting oil was purified via silica gel chromatography using a gradient of 30% ethyl acetate:hexane to afford Compound 20. MS-ES+ 277 1H NMR (400 MHz, DMSO-D6) 20: 11.37 (d, 1H), 10.24 (d, 1H), 8.45 (d, 1H), 8.09 (d, 2H), 7.68 (d, 1H), 7.43 (d, 2H), 7.28 (d, 1H), 6.46 (d, 1H), 6.44 (d, 1H), 5.79 (d, 1H), 2.30 (d, 1H).

The synthetic route of 1111637-94-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRIEN PHARMACEUTICALS LLC; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; Gangireddy, Paramareddy; Appalaneni, Rajendra P.; US2014/315909; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17570-98-8 , The common heterocyclic compound, 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, 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.

Example 6; 1 -(4-(1 -f6-methylpyridin-3-yl)-4-(pyridin-2-vO-1 H-imidazol-2-yltohenyl)-1 H-pyrrolor2.3- bipyridi?e; A mechanically stirred suspension of N’-(6-methylpyridin-3-yl)-4-(1H-pyrrolo[2,3- b]pyridin-1-yl)benzamidine (49.6 g, 152 mmol) in anhydrous THF (1 L) was treated over 30 mi? at less than 40C with a solution of LiHMDS (350 mL of 1M in THF). After 15 mi? at 0 0C the clear brown solution was treated portionwise at 3-6 0C with 2-bromo-1-(pyridin-2- yl)ethanone hydrobromide (42.6 g, 152 mmol) over 20 min. After being stirred 30 min at 00C and the mixture was warmed to 25 0C over 1h and stirred at 25 0C for 30 min. Water (500 mL) and EtOAc (1L) were added and the organic layer was separated, washed with brine, dried over Na2SO4, and concentrated. The residue was dissolved in 200 mL acetic acid and the resulting solution heated at 95 0C for 20 min and concentrated. The residue was dissolved in EtOAc (1L) and 2N HCI (450 mL). The organic layer was separated and washed with water (150 mL) and aqueous 10% citric acid (250 mL). The citric acid layer was extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with water, brine, dried, and concentrated giving 42 g of crude product as a brown oil which was purified by SGC (1% MeOH in DCM, 0.5 % NH4OH), giving the title substance in several fractions contaminated with 1-7% of the corresponding amide <4-(1H-pyrrolo[2,3-b]pyridin-1- yl)benzamide) as determined by HPLC (280 nM absorption ratio). Yield 15 g, 31%. The material was efficiently further purified by recrystallization as illustrated: a 4.5 g fraction containing 3.5% amide impurity was dissolved in 98:2 acetonitrile:water and the resulting solution stirred at RT fro 40 min. The crystalline precipitate was filtered, washed with fresh acetonitrile and dried giving 2.9 g of the title substance containing 0.3% amide. In this manner the remaining fractions were purified and the recrystallized solids combined giving 9.35 g of the title substance containing less than 1% amide impurity. 1H NMR (CDCI3) delta 8.58 (m, 2H), 8.37 (dd, 1H, J = 1.5, 4.8 Hz), 8.16 (d, 1H1 J = 7.9 Hz)1 7.97 (dd, 1H, J = 1.7, 7.9 Hz), 7.91 (br, 1H)1 7.82 (m, 2H)1 7.79 (td, 1H1 J = 1.7, 7.9 Hz), 7.62 (m, 2H)1 7.53-7.50 (m, 2H)1 7.24-7.19 (m, 2H), 7.15 (dd, 1H, J = 4.6. 7.9 Hz), 6.65 (d, 1 H, J = 3.7 Hz), 2.64 (s, 3H). MS (AP+) m/e 429 (MH+). Anal. Calcd for C27H20N6: C1 75.68; H1 4.70; N1 19.61. Found: C1 75.39; H1 4.52; N1 19.64. ICs0 = <3.21 nM The synthetic route of 17570-98-8 has been constantly updated, and we look forward to future research findings. Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/4117; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 234108-73-7 ,Some common heterocyclic compound, 234108-73-7, molecular formula is C10H13ClN2O2, 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 solution of 4-amino-2-chloropyridine (1.28 g, 10 mmol) and di-tert-butyl dicarbonate (2.21 g, 10.1 mmol) in TEtaF (20 mL) was cooled to O0C and a solution of IM lithium bis(trimethylsilyl)amide in TEtaF ( 20 mL, 20 mmol) was added slowly maintaining the temperature below O0C. The reaction was allowed to warm to room temperature over one hour and then quenched by the addition of 1.5 N aqueous ammonium chloride (15 mL). The mixture was extracted into ethyl acetate, washed with brine and the organic layer was dried (Na2SO4), filtered and evaporated. The residue was triturated with diethyl ether give pure tert-butyl (2-chloropyridin-4-yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 25 – 45% ethyl acetate/ hexane to afford more product.A solution of tert-butyl (2-chloropyridin-4-yl)carbamate (1.14 g, 5 mmol) in dry TBDF (20 rriL) was cooled to -700C under an inert atmosphere and 1.7 M t-butyl lithium/pentane (8 mL, 13.5 mmol) was slowly added. The reaction was stirred for two hours and then dry DMF (1.2 mL, 15.5 mmol) was added. The reaction was allowed to slowly warm to room temperature over a three hour period. The reaction mixture was quenched with 3 N HCl (12 mL) and diluted with diethyl ether. The ether layer was washed with aqueous NaHCtheta3, dried (over Na2SO4), filtered and evaporated. The residue was triturated with cold diethyl ether to give pure t-butyl (2-chloro-3-formylpyridm-4-yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 15-20% ethyl acetate/hexane to give additional product. lH-NMR(500 MHz, CDCI3): delta 11.0 (IH, br s), 10.52 (IH, s), 8.38 (IH, d, J= 6 Hz),8.31 (IH, d, J= 6 Hz), 1.54 (9H, s); m/e (m+1): 257.2.

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. 234108-73-7, tert-Butyl 2-chloropyridine-4-carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 727356-19-6 ,Some common heterocyclic compound, 727356-19-6, molecular formula is C6H5BrClN, 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.

Step 2; Preparation of 1-[5-(6-bromopyridin-2-yl)thiazol-2-yl]piperidin-4-yl}acetic acid tert-butyl ester (1-Thiocarbamoylpiperidin-4-yl)acetic acid tert-butyl ester (11.95 g, 46.3 mmol) obtained in Step 1 was added to a solution of 2-bromo-6-chloromethylpyridine (9.55 g, 6.3 mmol) obtained in Step 1 of Example 1 in ethanol (100 ml), and the mixture was heated at reflux overnight. The reaction solution was cooled to room temperature; dimethylformamide dimethylacetal (added 9.3 ml, 69.4 mmol) and triethylamine (19 ml, 139 mmol) were added and heated at reflux for 2 hours. After the reaction solution was concentrated, water was added, and it was extracted with ethyl acetate and washed with a saturated brine. The organic layer was dried over magnesium sulfate and the residue obtained by vacuum concentration was purified by chromatography on silica gel (n-hexane:ethyl acetate=50:50 to 0:100) and the title compound was obtained (13.09 g, 65%). 1H-NMR (400 MHz, DMSO-d6) delta: 7.95 (1H, s), 7.80 (1H, d, J=7.8 Hz), 7.67 (1H, t, J=7.8 Hz), 7.36 (1H, d, J=7.8 Hz), 4.02-3.95 (2H, m), 3.14-3.08 (2H, m), 2.20 (2H, d, J=7.2 Hz), 2.00-1.89 (1H, m), 1.79-1.72 (2H, m), 1.42 (9H, s), 1.34-1.21 (2H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,727356-19-6, its application will become more common.

Reference:
Patent; JAPAN TOBACCO INC.; US2006/205731; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem