Month: April 2022

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.1042986-00-4, name is 2-Fluoro-5-methylnicotinic acid, molecular formula is C7H6FNO2, molecular weight is 155.13, as common compound, the synthetic route is as follows.Recommanded Product: 2-Fluoro-5-methylnicotinic acid

Intermediate 9:2-fluoro-N-methoxy-N,5-dimethylnicotinamide[00366] To a solution of 2-fluoro-5-methylnicotinic acid (4.9 g, 31.6 mmol), N,O- dimethylhydroxylamine hydrochloride (4.01 g, 41.08 mmol), diisopropylethylamine (12.6 ml, 72.68 mmol) in dichloromethane (150 ml) at 0C was added TBTU (11.16 g, 34.76 mmol) portionwise over 30 minutes. The solution was stirred at 0C for a further 10 minutes then, at room temperature for 18 hours. The reaction mixture was washed with a 10wt% solution of citric acid and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography (ISCO Companion D, 8Og column, 0-20% EtOAc/Petrol) to afford the title compound as a colourless solid (5.44 g, 87% yield).[00367 ] 1H NMR (DMSO-d6, 400 MHz) delta 2.32 (3H, s), 2.69 (3H, s), 3.28 (3H, s), 7.92 (IH, dd), 8.15 (IH, s); MS (ES+) 199.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1042986-00-4, 2-Fluoro-5-methylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/94992; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 188577-68-6, 4,5-Dichloropyridin-2-amine, 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, name: 4,5-Dichloropyridin-2-amine, blongs to pyridine-derivatives compound. name: 4,5-Dichloropyridin-2-amine

a solution of phosgene (20% solution in toluene, 0.186 ml, 0.353 mmol) in THF (2 ml) was added triethylamine (0.141 ml, 1.01 mmol). To the resulting white suspension was added a solution7-(dimethoxymethyl)-1 ,2,3,4-tetrahydro-1 ,8-naphthyridine (intermediate 4, 70 mg, 0.336 mmol) inTHF (2 ml) drop wise. The resulting yellow suspension was stirred at room temperature for I h. 4,5- dichloropyridin-2-amine (65.7 mg, 0.403 mmol) in THF (1 ml) was added to the mixture and stirredroom temperature for 16 h. The reaction mixture was filtered through a silica gel plug and washed with heptanes/EtOAc 1:1(35 ml), the filtrate was concentrated. The residue was dissolveddioxane (1 ml) and treated with HCI (4 M in dioxane, I ml, 4.0 mmol). The mixture was stirred atroom temperature for 2 h, diluted with DCM and quenched with saturated aqueous NaHCO3. The org. layer was collected and the water layer was extracted with DCM. The combined org. layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was dissolved in acetonitrile/NMP/TFA, filtered through a syringe filter (0.2 pm) and purified by preparative reverse phase LC-MS (RP 1). The clean fractions were combined and lyophilized toobtain the title compound as an off white solid.1H NMR (400 MHz, DMSO-d5) 5 13.73 (s, IH), 9.94 (s, IH), 8.56 (s, IH), 8.34 (s, IH), 7.94 (d, IH),7.68 (d, IH), 4.03-3.95 (m, 2H), 2.95 (t, 2H), 2.01-1.90 (m, 2H).(UPLC-MS 1) Sample prepared in MeOH; tR 1.15, 1.28 mm; ESl-MS 383.1 [M+MeOH+H], 351.0[M+H].

The synthetic route of 188577-68-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BUSCHMANN, Nicole; FAIRHURST, Robin Alec; FURET, Pascal; KNOePFEL, Thomas; LEBLANC, Catherine; MAH, Robert; NIMSGERN, Pierre; RIPOCHE, Sebastien; LIAO, Lv; XIONG, Jing; ZHAO, Xianglin; HAN, Bo; WANG, Can; WO2015/59668; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 946002-90-0 , The common heterocyclic compound, 946002-90-0, name is (S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol, molecular formula is C9H11BrN2O, 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.

(S)-5-Bromo-2-[3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-1-yl]-pyridine (G2) To a sol. of compound G1 (20.9 g, 85.8 mmol) in DMF (350 mL) at 0 C. were added imidazole (14.6 g, 215 mmol) and TBDMS-Cl (19.4 g, 129 mmol). This mixture was stirred at rt for 1.5 h, and aq. 10% K2CO3 (150 mL) was added. The mixture was extracted with heptane (2*). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane/EtOAc 5:1?4:1?3:1?1:1) yielded the title compound (30.5 g, 99%).

The synthetic route of 946002-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bezencon, Olivier; Bur, Daniel; Corminboeuf, Olivier; Dube, Daniel; Grisostomi, Corinna; MacDonald, Dwight; McKay, Dan; Powell, David; Remen, Lubos; Richard-Bildstein, Sylvia; Scheigetz, John; Therien, Michel; Weller, Thomas; US2009/176823; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1211532-15-8 ,Some common heterocyclic compound, 1211532-15-8, molecular formula is C8H6F3NO3, 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.

Intermediate 37: Synthesis of 6-hydroxy-5-(trifluoromethyl)nicotinic acid; To a solution of TMSCI (0.75 ml_, 5.88 mmol) in dry MeCN is added potassium iodide (0.98 g, 5.88 mmol). The crude is stirred at room temperature for 10 mins. To this crude is added a solution of 6-methoxy-5-(trifluoromethyl)nicotinic acid (1 .3 g, 5.88 mmol) in MeCN (2 ml_). The crude is stirred at 80 deg C for 4 hrs and room temperature for overnight. The crude is concentrated and diluted in ether and 1 N HCI. The organic layer is washed with water, brine, dried over MgSO4, filtered and concentrated. The crude is purified via RP-HPLC (SunFire C18, H2O(O. I 0ZoTFA)ZCH3CN) to give 6-hydroxy-5-(trifluoromethyl)nicotinic acid (377 mg). HPLC retention time = 0.85 minutes (condition B); MS 208.0 (M+1 ). 1 H NMR (400 MHz, CD3OD) delta ppm 8.34 (s, 2 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. 1211532-15-8, 6-Methoxy-5-(trifluoromethyl)nicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; COPPOLA, Gary Mark; IWAKI, Yuki; KARKI, Rajeshri Ganesh; KAWANAMI, Toshio; KSANDER, Gary Michael; MOGI, Muneto; SUN, Robert; WO2010/136474; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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