Day: April 12, 2022

Application of 7169-95-1 ,Some common heterocyclic compound, 7169-95-1, molecular formula is C7H6BrN3, 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.

To a solution of 6-bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine (1 equiv) in DMF/H2O (9:1, 10 vol) was added compound S1 (1 equiv), K2CO3(2 equiv), and tetrakis(triphenylphosphine)palladium (0.1 equiv). The reaction mixture was stirred at 90 C. for 5 h and then concentrated. The remaining residue was purified by column chromatography on silica gel to give compound S3.

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. 7169-95-1, 6-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 27330-34-3 ,Some common heterocyclic compound, 27330-34-3, molecular formula is C6H6ClN3O, 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-Amino-5-chloropicolinic acid (106) Conc. HCl (38%, 32 mL, d=1.20, 400 mmol) was added to 3-amino-5-chloropicolinamide (105) (2.3 g, 13 mmol). The mixture was stirred and heated to reflux. The resulting solution was refluxed (100 C.) for 17 h. The resulting mixture was cooled to room temperature, then placed in the cold room for 3 h. The mixture was filtered, leaving the title compound as its hydrochloride salt, 2.1 g (66%); mp 235-236 C. 1 H NMR (DMSO-d6): delta6.68 (bs, 2H), 7.33 (d, J=1.8 Hz, 1H), 7.80 (d, J=2.1, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,27330-34-3, its application will become more common.

Reference:
Patent; State of Oregon, Acting by and Through the Oregon State Board of Higher Education, Acting for and on Behalf of the Oregon Health Sciences University and the University of Oregon; Cocensys, Inc.; US5801183; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 298709-29-2, 3,5-Difluoropicolinonitrile, 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, HPLC of Formula: C6H2F2N2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H2F2N2

To a solution of 3,5-difluoropicolinonitrile (10.0 g, 71.4 mmol) in THF (200 ml) was added methylmagnesium bromide (61.2 ml, 85.7 mmol) in THF solution at 0 0C. The reaction was stirred at room temperature for 1.5 hours. Saturated sodium bicarbonate solution (50 ml) was added, extracted with ether (100 ml), and dried over sodium sulfate. The solvent was removed. The residue (11.2 g, 71.28 mmol), hydroxylamine hydrochloride (9.907 g, 142.6 mmol) and sodium acetate (11.70 g, 142.6 mmol) in EtOH (100 ml) and water (50 ml) was heated at reflux for 3 hours. The solvent was removed and diluted with 50 ml of saturated sodium bicarbonate and extracted with EtOAc (2 x 200 ml). After dried over sodium sulfate, the solvent was removed and the title compound was used directly in next step without purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,298709-29-2, 3,5-Difluoropicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/123113; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153034-88-9, 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. 153034-88-9, name is 2-Chloro-4-iodo-3-methylpyridine, molecular formula is C6H5ClIN, 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.

Under inert gas atmosphere 0.80 g (2.53 mmol) of example XIII.1 , 0.65 g (2.53 mmol) of 2-chloro-4-iodo-3-methyl-pyridine, 1.00 g (10.4 mmol) NaOtBu and 100 mg (0.14 mmol) chloro(2-dicyclohexylphosphino-2’>4′,6′-triisopropyl-1 , 1 ‘-biphenyl)(2-(2- aminoethyl)-phenyl)-palladium (II) are added to 50 mL dioxane and stirred at 45 C over night. Afterwards the solvent is removed, water is added and the product is extracted with EtOAc. The organic layer is dried over MgS04, filtered and the solvent is removed in vacuo. The crude product is purified by HPLC (ACN/H20/TFA). C20H24CIN3O2 (M= 373.9 g/mol) ESI-MS: 374 [M+H]+ Rt (HPLC):0.77 min (method M)

According to the analysis of related databases, 153034-88-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; WO2014/114578; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 10128-72-0, 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 10128-72-0, name is Methyl 3-hydroxyisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 30: methyl 3-I(4-phenylbutyl)oxyl-4-pyridinecarboxylate To a solution of methyl 3-hydroxy-4-pyridinecarboxylate (100 mg, 0.65 mmol) in DMF (2 ml) wasadded cesium carbonate (426 mg, 1 .31 mmol) followed by (4-bromobutyl)benzene (139 mg, 0.65mmol). The mixture was allowed to stir at room temperature for 16 h then concentrated in vacuo. The crude product was dissolved in DMSO (1 ml) and purified by MDAP using a formic modifier (Method G). Fractions containing desired product were loaded directly onto a 5g SCX-ll SPE column that had been preconditioned with isopropylalcohol. The column was eluted with isopropylalcohol (3 x 50 ml)then with a 10% ammonia inwater/90% isopropylalcohol solution. Desired product eluted in ammonia based fractions which were combined then concentrated under reduced pressure to give the title compound as a pale brown gum (1 23mg, 66%).LCMS (Method B): Rt= 1.19 mins, MH+ = 286.1

According to the analysis of related databases, 10128-72-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; BARKER, Michael David; CAMPBELL, Matthew; DIALLO, Hawa; DOUAULT, Clement; HUMPHREYS, Philip; LIDDLE, John; SHEPPARD, Robert John; THOMAS, Pamela Joan; WILSON, David Matthew; WO2013/143597; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 18368-59-7, 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 18368-59-7, name is 3-Bromo-4-methylpyridin-2-ol. This compound has unique chemical properties. The synthetic route is as follows.

Example 195; Synthesis of 3-iodo-4-methyl-1-(3-(trifluoromethoxy)phenyl)pyridin-2? HP-one; A resealable pressure vessel was charged with copper(l) iodide (0.081 g, 0.425 mmol), 1-iodo-3-(trifluoromethoxy)benzene (0.434 ml, 2.77 mmol) and 3-bromo-4- methylpyridin-2(1H)-one (0.400 g, 2.13 mmol). To the mixture was added dioxane (3 ml.) followed by N1,N2-dimethylethane-1,2-diamine (0.092 ml, 0.851 mmol). The vessel was purged with Argon, sealed, and heated to 1100C for 24 hrs. The mixture was cooled to RT, diluted with EtOAc and washed with water and brine. The organic fraction was adsorbed onto silica gel and purified by silica gel chromatography using 15-80% Hexanes:EtOAc to afford 3-iodo-4-methyl-1- (3-(trifluoromethoxy)phenyl)pyridin-2(1 H)-one as an off-white solid. M+H+ = 396.0.

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 18368-59-7, 3-Bromo-4-methylpyridin-2-ol.

Reference:
Patent; AMGEN INC.; WO2008/11109; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 327056-62-2 ,Some common heterocyclic compound, 327056-62-2, molecular formula is C6H3FN2, 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.

2) 2-[(5-Fluoropyridine-2-carbonyl)amino]malonic acid diethyl ester A 6 N aqueous solution of hydrochloric acid (100 mL) containing the 5-fluoropyridine-2-carbonitrile (11.8 g) was heated to reflux for 4 hours. After air cooling, Nacl was added to the reaction solution for saturation, and ethyl acetate was further added thereto. The resultant mixture was partitioned, and the organic layer was dried over anhydrous sodium sulfate. After separating the organic layer by filtration, the solvent was evaporated under reduced pressure, and a residue thus obtained was dissolved in N,N-dimethylformamide (140mL). Then, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.0 g), 1-hydroxybenzotriazole (770mg), and aminomalonic acid diethyl ester hydrochloride (7.2 g) were added to the solution, and the resultant mixture was stirred at room temperature for 19.5 hours. Water and ethyl acetate were added to the reaction solution, and the mixture was partitioned. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. After separating the organic layer by filtration, the solvent was evaporated under reduced pressure, and a residue thus obtained was purified by silica gel column chromatography (hexane-ethyl acetate), to obtain 2-[(5-fluoropyridine-2-carbonyl)amino]malonic acid diethyl ester (9.4 g, 53%) as a solid. 1H-NMR (400MHz, CDCl3) delta: 1.33 (6H, t, J=7.1Hz), 4.27-4.38 (4H, m), 5.36 (1H, d, J=7.4Hz), 7.51-7.56 (1H, m), 8.20-8.21 (1H, m), 8.46 (1H, d, J=2.7Hz), 8.74 (1H, d, J=10.0Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,327056-62-2, its application will become more common.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1803719; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153747-97-8, 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 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of tert -butyl 4-(5-bromopyridin-2-yl)piperazine-l-carboxylate (250 mg, 0.730 mmol) in 2.5 mL anhydrous THF was added 2.5 M w-butyllithium (320 muL, 0.80 mmol) at -78 0C under nitrogen atmosphere. After stirring for 45 mins, the reaction mixture was charged with dimethyl phosphinic chloride (164.4 mg, 1.46 mmol) in 1 mL anhydrous THF. The reaction mixture was warmed to -30 0C over 3 h. The mixture was quenched with saturated ammonium chloride aqueous solution and the mixture was partitioned between DCM and brine. The organic layer was dried over Na2SO4 and concentrated to afford the crude material. The resulting solid was purified by flash chromatography on silica gel, eluting with 20 – 100% EtOAc : heptane. Fractions containing the desired product were combined and concentrated to afford an off white solid (100 mg, 40.3% yield). The Boc protected title compound was dissolved in 2-PrOH (1 mL) and charged with 4 N HCl. The reaction mixture was heated at 70 0C for 30 min, and concentrated to afford the titled product as a HCl salt. MS (m/z, MH+): meas. 240.2 calc. 240.3

According to the analysis of related databases, 153747-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 135450-23-6 ,Some common heterocyclic compound, 135450-23-6, molecular formula is C7H5ClN2, 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.

To a solution of commercially available chloride 30 (9.66 g,63.3 mmol) in DMF (400 mL) at ambient temperature was treatedwith potassium phthalimide (11.7 g, 63.3 mmol). After stirring for5 h, the mixture was concentrated under vacuum. The remainingmixture was taken up in H2O (200 mL) and was filtered to collectthe solid. The solid was washed with H2O (100 mL) and THF(100 mL) to obtain the desired phthalimide derivative (11.5 g,69%) and was moved forward without further purification. To asolution of the crude phthalimide derivative (5.84 g, 22.2 mmol)in THF/MeOH (200 mL, 1:1, v/v) at ambient temperature was treatedwith hydrazine monohydrate (1.18 mL, 24.4 mmol). After 2 h,1.0 M HCl (24.5 mL) was added to the mixture and was stirredfor another 3 h before concentrating the reaction mixture undervacuum. The remaining residue was taken up in H2O (200 mL)and the unwanted solid was removed through filtration. The filtratewas concentrated and placed under vacuum to remove theremaining H2O. The crude solid was taken up in CH2Cl2 (175 mL)and triethylamine (9.28 mL, 66.6 mmol) and Boc2O (4.86 g,24.4 mmol) was added. After stirring for 12 h at room temperature,the reaction was quenched with a saturated solution of NaHCO3(200 mL), extracted with CH2Cl2 (3 150 mL), dried over MgSO4,and concentrated under reduced pressure. The residue was purifiedusing flash chromatography (10-45% ethyl acetate in hexanes)to provided the aryl pyridine ?IN? fragment (2.24 g, 43%): 1H NMR(CDCl3, 400 MHz) d 7.78 (t, J = 7.6 Hz, 1H), 7.56 (d, J = 7.6 Hz, 1H),7.49 (d, J = 8.0 Hz, 1H), 5.51 (s, 1H), 4.44 (d, J = 5.6 Hz, 2H), 1.43(s, 9H); 13C NMR (CDCl3, 100 MHz) 160.1, 155.9, 137.6, 133.0,127.0, 125.1, 117.1, 79.9, 45.5, 28.3; IR (neat) 3347, 2979, 2934,2239, 1699, 1518, 1453, 1250, 1170, 862; HRMS (ESI) m/z calcdfor C12H15N3NaO3 [M+Na]+ 256.1062, found 256.1062.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135450-23-6, its application will become more common.

Reference:
Article; Clausen, Dane J.; Smith, William B.; Haines, Brandon E.; Wiest, Olaf; Bradner, James E.; Williams, Robert M.; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 5061 – 5074;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 23628-31-1 ,Some common heterocyclic compound, 23628-31-1, molecular formula is C6H6N2O2, 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.

To a solution of 2-amino-6-pyridinecarboxylic acid (6.0 g, 43.5 mmol) in ethanol (150 mL) was added thionyl chloride (12.0 g, 101 mmol) at 0 C. The resulting reaction mixture was stirred at reflux for 12 h. Upon cooling to room temp, the reaction mixture was concentrated under reduced pressure. Saturated aqueous Na2CO3 solution was added until the pH of the solution reached 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temp for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate (5.5 g, 76 % yield).

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. 23628-31-1, 6-Aminopicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GlaxoSmithKline LLC; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; (583 pag.)EP2768509; (2017); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem