Tag: M.W:200-300

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. 619331-71-4, name is 4,7-Dibromo-1H-pyrrolo[2,3-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 619331-71-4

A mixture of 4,7-dibromo-lH-pyrrolo[2,3-c]pyridine (946 mg, 3.43 mmol), Nal (2.08 g, 13.7 mmol), Cul (33 mg, 0.17 mmol), and trans-N,N’-dimethylcyclohexane-l, 2-diamine (51 mg, (1779) 0.35 mmol) in l,4-dioxane (10 mL) was stirred at 90 C under argon for 4 h. LC/MS showed complete conversion was achieved (LC-MS 323.0, 325.0 [M+H]+, RT 1.30 min). The solvent was removed and the residue was suspended in ethyl acetate and filtered. The filtrate was washed with NH4CI (aq.), water and brine, dried over anhydrous Na2S04 and concentrated. The material obtained was dissolved in dichloromethane (20 mL) and treated with di-tert-butyl dicarbonate (1.20 mL, 5.1 mmol) and a few crystals of 4-dimethylaminopyridine. After stirring at room temperature for 2 h, the mixture was concentrated and chromatographed on a silica gel column (ethyl acetate in hexames, 0 – 50%) to provide tert-butyl 4-bromo-7-iodo-pyrrolo[2,3-c]pyridine- l-carboxylate (1.41 g, 97%) as a pink oil. LC-MS 423.3, 425.3 [M+H]+, RT 1.69 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, 619331-71-4, 4,7-Dibromo-1H-pyrrolo[2,3-c]pyridine.

Reference:
Patent; PTC THERAPEUTICS, INC.; CHEN, Guangming; BHATTACHARYYA, Anuradha; JIANG, Yao; KARP, Gary, Mitchell; NARASIMHAN, Jana; TURPOFF, Anthony; ZHANG, Nanjing; (0 pag.)WO2020/5882; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 90145-48-5 ,Some common heterocyclic compound, 90145-48-5, molecular formula is C6H5BrN2O, 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.

5-methoxybenzofuran boronic acid (1.2 mmol), 5-bromopyridine-2-carboxamide (1.0 mmol), Pd(PPh3)2Cl2 (0.024 mmol) and NEt3 (317 muL) were mixed in EtOH (10 mL) in a 20 mL microwave vial. The mixture was stirred at 140 C. for 10 min in a microwave reactor, filtered, and the precipitate was washed with water and EtOAc and dried under vacuum to afford the title compound (75 mg). 1H NMR delta ppm 9.10 (d, 1H) 8.34 (dd, 1H) 8.21 (br. s., 1H) 8.00 (d, 1H) 7.52-7.72 (m, 3H) 7.25 (d, 1H) 7.00 (dd, 1H) 3.82 (s, 3H); MS m/z 269 (M+H).

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. 90145-48-5, 5-Bromopyridine-2-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; US2008/221149; (2008); 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. 917918-84-4, name is 2-Bromo-5-fluoro-4-methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H4BrFN2O2

Example 7; Preparation of Compound J’ from Compound da; Compound da (800 g, 3.404 mol), lithium methoxide (12.9 g, 0.34 mol) and DMF (5.6 L) was charged to an inert 20 L Korzun reactor. Then DMF-dimethyl acetal c. (2.02 kg, 17.1 mol) was added. The resulting homogeneous solution was warmed to 80-85 C. and held at this temperature until HPLC analysis of the crude reaction mixture indicated that less than 0.5 relative area percent (RAP) of compound da remained. The reaction mixture was cooled to 5-10 C. Water (9 L) was charged to the reactor maintaining the temperature below 45 C. The resulting slurry was cooled to 0-5 C. and held at this temperature for 1 h. The crystals were collected via filtration. The cake was washed with deionized water (6 L) and dried at 45 C. under vacuum to give J’ as a light brown solid (890 g, 90%, HPLC AP 98.1). 1H NMR (300 MHz, d6-DMSO) delta8.02 (d, JF-H=4.2 Hz, 1H), 7.47 (dd, J=13.0 Hz, JF-H=1.7 Hz, 1H), 4.20 (d, J=13.0 Hz, 1H), 3.14 (s, 6H); 13C NMR (75 MHz, d6-DMSO): delta153.9 (d, JF-C=255 Hz), 151.6, 151.4, 141.9, 136.4 (d, JF-C=27 Hz), 131.0 (d, JF-C=15 Hz), 126.1 (d, JF-C=2 Hz), 78.8.

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, 917918-84-4, 2-Bromo-5-fluoro-4-methyl-3-nitropyridine.

Reference:
Patent; Bristol-Myers Squibb Company; US2006/293304; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89364-04-5, 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.89364-04-5, name is 3-Bromo-4-nitropyridine, molecular formula is C5H3BrN2O2, molecular weight is 202.9935, as common compound, the synthetic route is as follows.

After the phenothiazine 20.0g (100.36mmol), 3-Bromo-4-nitro-pyridine 23.18 g (110.40mmol), the NaO (t-Bu)14.46 g (150.55 mmol), the Pd 2 (dba) 3 2.757 g (3.01mmmol) was suspended in the toluene 400 mL P (t-Bu)3 1.46 mL (6.02 mmol) was put and it mixed reflux under the nitrogen air current for 24 hours. It extracts in the dichloromethane and distilled water and the organic layer the silica gel is filtered. Hexane the organic solution is removed: it recrystallized as the dichloromethane and ethyl acetate and it obtained the intermediate product (C) 23.22 g (yield : 72 %) by the dichloromethane= 7 : 3 (v/v) after the silica gel column.

Statistics shows that 89364-04-5 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-4-nitropyridine.

Reference:
Patent; Cheil Industries Co., Ltd.; Jang, Yuna; Hong, Jin Suk; Kang, Dong Min; Sin, Ji Hun; Yu, Dong Gyu; Yu, Uhn Sun; Lee, Byung Kwan; Lee, Sang Sin; Lee, Han Ir; Jung, Su Young; Han, Su Jin; (34 pag.)KR2015/41508; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89640-55-1 ,Some common heterocyclic compound, 89640-55-1, molecular formula is C6H6INO, 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: tert-Butyl (1-(4-((4-methoxypyridin-3-yl)ethynyl)phenyl)cyclobutyl)carbamate: To a solution of 3-iodo-4-methoxypyridine (500 mg, 2.127 mmol) in anhydrous triethylamine (9ml) was added bis(tert-butylphosphine)palladium(0) (65 mg, 0.128 mmol) and copper(l) iodide (12.2 mg, 0.064 mmol). The reaction mixture was degassed with N2 for 10 min before being cooled to 0C. A degassed solution of tert-butyl 1-(4- ethynylphenyl)cyclobutylcarbamate (635 mg, 2.34 mmol) in TEA (2 ml) was added dropwise to the cooled reaction mixture. The reaction was allowed to warm to RT and stirred for 18 h. The reaction mixture was concentrated in vacuo and the residue diluted with DC (20 ml) and water ( 0 ml). The phases were separated and the organic layer dried (Na2S04), filtered and concentrated affording a brown oil that was purified by silica gel chromatography (gradient 0 to 50% ethyl acetate in hexanes) yielding the title compound as a brown gum (140 mg, 17%). 1H NMR (500 MHz, CDCI3): delta 8.54 (br s, 1 H), 8.38 (br s, 1 H), 7.46 (d, 2H), 7.34 (d, 2H), 6.77 (d, 1 H), 5.10 (s, 1 H), 3.90 (s, 3H), 2.4-2.5 (m, 4H), 2.0-2.1 (m, 1 H), 1.75-1.86 (m, 1 H), 1.1-1.4 (br s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89640-55-1, its application will become more common.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BELL, Mark, Peter; O’DOWD, Colin, Roderick; ROUNTREE, James, Samuel, Shane; TREVITT, Graham, Peter; HARRISON, Timothy; MCFARLAND, Mary, Melissa; WO2011/55115; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 228410-90-0 , The common heterocyclic compound, 228410-90-0, name is 5-bromo-2-hydroxy-3-nitro-4-picoline, 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.

Step 1. 5-Bromo-1,4-dimethyl-3-nitropyridin-2(1H)-one A solution of 5-bromo-4-methyl-3-nitropyridin-2-ol (15.00 g, 64.37 mmol) [Combi-Blocks, AN-1086] in N,N-dimethylformamide (250 mL) was treated with sodium hydride (3.09 g, 77.3 mmol) (60% dispersion on mineral oil) slowly and portionwise, and stirred at RT for 30 min. The reaction mixture was treated with methyl iodide (4.81 mL, 77.2 mmol) dropwise and stirred at RT for 3 h. LCMS indicated a clean peak for methylated product. The reaction mixture was poured over water/ice (?400 mL) and allowed to stir while the ice melted. The aqueous mixture was extracted with EA. The organic layer was washed with water (3*) and brine, dried with magnesium sulfate, filtered, and concentrated to give the desired product (14.9 g, 93%) that was used without further purification. LCMS calculated for C7H8BrN2O3 (M+H)+: m/z=247.0, 249.0. found: 247.0, 248.9.

The synthetic route of 228410-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Yue, Eddy W.; Combs, Andrew P.; Buesking, Andrew W.; US2015/148375; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 20511-12-0 , The common heterocyclic compound, 20511-12-0, name is 5-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.

Bromine (3ml) was added dropwise to a solution of 2-amino-5-iodo-pyridine (5g, 20mmol) in 48% hydrobromic acid in water (10ml). AIL ice bath was used to cool the system. Sodium nitrite (3.4 g in 5ml of water) was then added dropwise so that the temperature does not go above 15C. After the addition was complete, sodium hydroxide (16g) in water (40ml) was added. Brown solid precipitated and was extracted with DCM (50ml). The DCM extract was washed with water, brine, dried over MgS04 and evaporated in vacuo to give 2-bromo-5-iodo-pyridine (4.4g, 78%).

The synthetic route of 20511-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F2G LTD; WO2005/92304; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, 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: 17570-98-8, blongs to pyridine-derivatives compound. SDS of cas: 17570-98-8

2-Bromo-1-(pyridin-2-yl)ethanone hydrobromide 8a(20.0 g, 71.1 mmol) and K2CO3 (14.8 g, 107 mmol) were suspended in acetone (100 mL), andthe suspension was stirred at room temperature for 1.5 hr. To a solution of ethyl cyanoacetate (60.4 g, 534 mmol) in acetone (100 mL) was addedK2CO3 powder (29.6 g, 214 mmol), and the mixture was stirred at 45C for 1 hr. To this mixture was added dropwise the suspension obtained earlier by small portions at 45C, and the resulting mixture was stirred at 45C for 3 h, filtered after cooled to room temperature, and then concentrated under reduced pressure. The residue was taken up withEtOAc, washed with H2O and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. To the obtained oil was added 4 mol/L HCl/EtOAc (250 mL) and the mixture was stirred at 60 C for 3 h, and concentrated under reduced pressure. A solution ofNaHCO3 was added to the residue and the mixture was extracted with EtOAc, washed with brine, dried over anhydrous MgSO4,and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/EtOAc = 4/1), then added dropwise 4 mol/L HCl/EtOAc (20 mL) after dissolved in EtOAc (20 mL), concentrated under reduced pressure, and crystalized from EtOAc to yieldcompound 10a (3.08 g, 15%) as a colorless solid: 1H-NMR (DMSO-d6)d 1.30 (3H, t, J=7.0 Hz), 4.25 (2H, q, J=7.0 Hz), 7.48-7.54 (2H, m), 8.13-8.19 (2H, m), 8.61-8.63 (1H, m), 13.47 (1H, br), 1H not detected.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, and friends who are interested can also refer to it.

Reference:
Article; Nishida, Haruyuki; Arikawa, Yasuyoshi; Hirase, Keizo; Imaeda, Toshihiro; Inatomi, Nobuhiro; Hori, Yasunobu; Matsukawa, Jun; Fujioka, Yasushi; Hamada, Teruki; Iida, Motoo; Nishitani, Mitsuyoshi; Imanishi, Akio; Fukui, Hideo; Itoh, Fumio; Kajino, Masahiro; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3298 – 3314;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1049744-89-9 ,Some common heterocyclic compound, 1049744-89-9, molecular formula is C6H7ClF3N3, 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 5-(4-methoxyphenyl)-1,2,4-oxadiazole-3-carbaldehyde (500 mg, 2.40 mmol) and2-hydrazino-5-(trifluoromethyl)pyridine hydrochloride(877 mg, 2.52 mmol) in MeCN (10 n) was stirred atRT for 3 h. The resulting suspension was diluted with water (10 mL) and filtered. The filter cake was washed with water (10 mL) and dried overnight invacuum oven (50 C, 20 mbar) to give the title compound as a brown solid (630 mg, 1.73 mmol, 72%,Ca. 90:10 mixture of stereoisomers).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1049744-89-9, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; KENNEDY, Jason W. J.; VON MORGENSTERN, Sascha; (37 pag.)WO2016/135062; (2016); 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. 1440519-73-2, name is 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one. A new synthetic method of this compound is introduced below., Recommanded Product: 1440519-73-2

General procedure: Procedure A: To a solution of 5-bromo-2-(4-methoxybenzyl)isoindolin-1-one (1, 0.5 g, 1.5 mmol) in dioxane (10 mL) was added 7H-pyrrolo[2,3-d]pyrimidine (2, 0.27 g, 2.25 mmol) and potassium tert-butoxide (0.51 g, 4.52 mmol) followed by the addition of XantPhos (0.087 g, 0.15 mmol). The reaction mixture was degassed with argon for 15 min. Tris(dibenzylideneacetone)dipalladium(0) (0.14 g, 0.15 mmol) was then added and the reaction mixture was heated at 90 C. and maintained at that temperature for 12 h. (0193) Following heating, the reaction mixture was cooled and concentrated under reduced pressure. The concentrated reaction mixture was extracted in ethyl acetate. The organic layer was separated, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue obtained was purified by silica gel (100-200 mesh) column chromatography using 5% methanol in dichloromethane as eluent so as to afford 2-(4-methoxybenzyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-one (3). Yield: 0.21 g, 38%;

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, 1440519-73-2, 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem