Day: April 14, 2022

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

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

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

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 23628-31-1, name is 6-Aminopicolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 23628-31-1

(3) Ethyl 6-aminopyridine-2-carboxylate 6-Aminopyridine-2-carboxylic acid (5.1 g) was dissolved in ethanol (100 mL). Concentrated sulfuric acid (4 mL) was added and the mixture was heated under reflux for 23 hours. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. Water was added to the residue, followed by neutralization with a saturated sodium bicarbonate solution under ice-cooling. The reaction mixture was extracted with chloroform twice. The organic layers were washed with a saturated sodium chloride solution and dried over magnesium sulfate. The drying agent was removed by filtration and then the solvent was evaporated under reduced pressure. The title compound (4.75 g) was obtained as a residue. 1H-NMR (400 MHz, CDCl3) delta(ppm): 1.41 (t, J=7.2 Hz, 3H), 4.43 (q, J=7.2 Hz, 2H), 4.68 (br s, 2H), 6.65 (dd, J=1.2 Hz, 8.0 Hz, 1H), 7.47 (dd, J=1.2 Hz, 7.2 Hz, 1H), 7.53 (dd, J=7.2 Hz, 8.0 Hz, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 23628-31-1.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2017275; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 67058-71-3, 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 67058-71-3 as follows.

To a suspension of NaH (60 % in mineral oil, 90 mg, 2.25 mmol) in DMF (4.2 mL) cooled at 0C was added a solution of 1-(1 H-pyrrolo[2,3-c]pyridin-3-yl)-ethanone (prepared according to J. Org. Chem. 2002, 67, 6226) (300 mg, 1.87 mmol) in DMF (4.2 mL) and the resulting suspension was stirred at 0C under nitrogen atmosphere for 30 min before slow addition of tert-butyl bromoacetate (277 mu, 1.87 mmol). The reaction mixture was allowed to reach RT and further stirred at RT for 1.5 h. After completion of the reaction, the mixture was purified first by catch-release on SiliaPrep Tosic Acid-(2×10 g) (Varian) (eluent: MeOH (50 mL) by 2 M ammonia in MeOH (50 mL)) to give a mixture of regioisomers: (3-acetyl-pyrrolo[2,3-c]pyridin- 1-yl)-acetic acid tert-butyl ester and (3-acetyl-pyrrolo[2,3-c]pyridin-6-yl)-acetic acid tert-butyl ester followed by flash column chromatography on silica gel (CH2CI2 to CH2CI2/MeOH 85-15) to give (3-acetyl-pyrrolo[2,3-c]pyridin-1-yl)-acetic acid tert-butyl ester as a yellow powder. TLC, Rf (CH2CI2/ MeOH 9-1) = 0.50; MS (UPLC/MS): 275.3 [M+H]+, 319.2 [M+HCOO]-; tR (HPLC conditions f): 1.28 min; 1 H-NMR (400 MHz, DMSO-d6): delta (ppm): 8.88 (s, 1 H), 8.50 (s, 1 H), 8.33 (d, 1 H), 8.06 (d, 1 H), 5.27 (s, 2H), 2.48 (s,3H), 1.45 (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,67058-71-3, its application will become more common.

Reference:
Patent; NOVARTIS AG; ALTMANN, Eva; HOMMEL, Ulrich; LORTHIOIS, Edwige Liliane Jeanne; MAIBAUM, Juergen Klaus; OSTERMANN, Nils; QUANCARD, Jean; RANDL, Stefan Andreas; SIMIC, Oliver; VULPETTI, Anna; ROGEL, Olivier; WO2012/93101; (2012); A1;,
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

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

Reference of 920966-03-6 ,Some common heterocyclic compound, 920966-03-6, molecular formula is C8H5ClN2O2, 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 compound 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid 11a (1.00 g, 5.10 mmol) and DMF (10 mL) were added to the reaction flask, was added CDI (0.91g, 5.61mmol), stirred at room temperature for 1 hour and ice-water bath, followed by addition of NH3.H2O (1.12mL) at 0 C, stirred at room temperature for 1 hour. TLC monitored the reaction was complete, the system was poured into water, extracted three times with ethyl acetate, washed with water, and the combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and concentrated, dichloromethane / petroleum ether = 5ml / 1ml beating, suction filtration, dried under reduced pressure using a rotary evaporator to give the title compound 11b (0.6g, 3.08mmol), in a yield of 60.3%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,920966-03-6, its application will become more common.

Reference:
Patent; Shanghai Huahuituo Pharmaceutical Technology Co., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd.; Xu Xin; Zhang Tian; Li Yunfei; Wang Guan; Zhu Weibo; Li Qiang; Qu Minkai; Zhang Linli; Song Jinqian; Liu Lei; Chen Haiji; Liu Qiang; Wang Yijin; Ge Jian; (67 pag.)CN109535164; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 850663-54-6, 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. 850663-54-6, name is 4-Chloro-5-nitropyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

Into a 250 mL 3 -necked round-bottom flask purged and maintained with nitrogen was added a solution of 4-chloro-5-nitropyridin-2-ol (1 1.5 g, 65.9 mmol) in CH3CN (1 10 mL), followed by addition of POBr3 (23.1 g). The resulting solution was stirred at 80 C for 2 hours. The solids were filtered out and the filtrate was concentrated under vacuum. The residue was suspended in 500 mL of ice water. The resulting solids were collected by filtration and dried under vacuum to afford 2,4- dibromo-5-nitropyridine (7.66 g, 41.1%) as a light yellow solid, which was carried forward without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,850663-54-6, its application will become more common.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); 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. 53710-18-2, name is 3,5-Diiodopyridine, molecular formula is C5H3I2N, 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. Recommanded Product: 3,5-Diiodopyridine

In a 75-mL sealed tube, 3,5-diiodo-pyridine (intermediate A-5, 6.6 g, 20 mmol), 5-chloro- 3,3-dimethyl-2,3-dihydro-isoindol-1-one (intermediate A-3, 1.95 g, 10 mmol), CuT (571 mg, 3 mmol), K3P04 (4.24 g, 20 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.7 mL, 6 mmol) were dissolved in 20 mL of dioxane. The resulting reaction mixture was heated at120C for 3 hours before it was poured into water (50 mL) and extracted with EtOAc (2 x125 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product, which was purified by silica gel flash chromatography (0-30% EtOAc-hexane gradient) to yield the title compound (1.8 g, 45%) as a light yellow solid. MS: 399.2 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 53710-18-2.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191338; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem