Tag: M.W:100-200

Synthetic Route of 116308-35-1, 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 116308-35-1 as follows.

A solution of 2-(trifluoromethyl)nicotinaldehyde (1.96 g, 11.19 mmol) and hydroxylamine hydrochloride (0.856 g, 12.31 mmol) in pyridine (6 mL) was stirred at rt for 1 h. Pyridine was removed under vacuum to give the desired product (2.12 g, 100%) as a white solid: LCMS (ES): m/z 191.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,116308-35-1, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; FENG, Jianxin; LIU, Chunjian; HUANG, Yanting; (130 pag.)WO2019/89665; (2019); A1;,
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 5006-66-6, name is 6-Oxo-1,6-dihydropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 5006-66-6

Example 148; Preparation of 5-(fro[2,3-b]pyridin-5-yl)-3-((4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-propylphenoxy) pyridin-2-yl)methyl)-5-methylimidazolidine-2,4-dione; 148-a-1) Preparation of ethyl 6-hydroxynicotinate; To a solution of 6-hydroxynicotinic acid (5.0 g, 35.9 mmol) in ethanol (180 mL), sulfuric acid (1.0 mL) was added. The resultant mixture was stirred at 60° C. for 20 minutes, then added with surfuric acid (33.0 mL), and stirred for 6.5 hours while heated to reflux. The reaction solution was then added with a saturated aqueous solution of sodium hydrogen carbonate under ice-cold conditions and ethanol was concentrated in vacuo. After extracted with ethyl acetate, the organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. Ethyl 6-hydroxynicotinate (5.33 g, yield 89percent) was obtained as a white crystal.1H-NMR (CDCl3) delta: 1.36 (3H, t, J=7.1 Hz), 4.33 (2H, q, J=7.1 Hz), 6.58 (1H, d, J=9.5 Hz), 8.01 (1H, dd, J=2.4, 9.5 Hz), 8.19 (1H, d, J=2.4 Hz), 12.43 (1H, brs).

With the rapid development of chemical substances, we look forward to future research findings about 5006-66-6.

Reference:
Patent; KOWA COMPANY, LTD.; US2010/48610; (2010); 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. 16744-81-3, name is 4-Methoxypicolinaldehyde, the common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Methoxypicolinaldehyde

To a cooled (0 °C) solution of 18 (93 mg, 0.67 mmol) and 21 (77 mg, 0.56 mmol) in dry dichloromethane (1 mL) was added NaBH(OAc)3 (178 mg, 0.84 mmol). The reaction mixture was stirred at rt for 6 hr. The reaction was quenched with water, the mixture was diluted with sat. NaHCO3, and then extracted with CHCl3. The extracts were dried over MgSO4 and concentrated by evaporation to give the crude product. To a solution of the product in dry CH2Cl2 (1 mL) was added dropwise the solution of Boc2O (292 mg, 1.34 mmol) in dry CH2Cl2 (2.0 mL). The reaction mixture was stirred at rt overnight. After dilution with sat. NaHCO3, the mixture was extracted with CHCl3. The extracts were dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on SiO2 (CH3Cl :MeOH : NH3 = 100 : 1 : 0.1 ? 40 : 0.1) to give 22 (156 mg, 78 percent) as a yellow oil.

The synthetic route of 16744-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fuchida, Hirokazu; Tabata, Shigekazu; Shindo, Naoya; Takashima, Ippei; Leng, Qiao; Hatsuyama, Yuji; Hamachi, Itaru; Ojida, Akio; Bulletin of the Chemical Society of Japan; vol. 88; 6; (2015); p. 784 – 791;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 176526-00-4, Adding some certain compound to certain chemical reactions, such as: 176526-00-4, name is 2-(Pyridin-4-yl)benzaldehyde,molecular formula is C12H9NO, 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 176526-00-4.

A solution of tetrabutylammonium fluoride (0.027 ml; 1.0 M in tetrahydrofuran) was added to a solution of 2-pyridin-4-yl-benzoAldehyde (500 mg, 2.73 mmol) and trifluoromethyltrimethylsilane (TMSCF3) (485 mul, 3.28 mmol) in 5 ml of THFin. The resulting mixture was warmed to room temperature and stirred at room temperature for 4 hours. The reaction mixture was then washed with 5 ml of 1N HClAnd stirred overnight at room temperature. The solvent was evaporated to dryness, 9 ml of a 1 M aqueous solution of sodium carbonate was added and the aqueous phase was extracted with chloroform (3 x10 ml), the combined chloroform layers were washed with water and dried over MgSO4. Evaporation of the organic solvent gave 300 mg of 2,2,2-trifluoro-l- (2-Pyridin-4-yl-phenyl) ethanol in a yield of 43%.

According to the analysis of related databases, 176526-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laixiken Pharmaceutical Co., Ltd.; A Luojiyasami·dewasajiayalayi; Jin Haihong; Shi Zhicai; A Xiaoke·tunuli; Wang Ying; Zhang Chengmin; (63 pag.)CN104045626; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 99368-68-0 ,Some common heterocyclic compound, 99368-68-0, molecular formula is C6H4ClF3N2, 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.

B. To compound 27a (0.241 g, 1.23 mmol) in 4 mL CH3CN was added iPr2NEt (0.24 mL, 1.38 mmol) and compound 20b (0.24 mL, 1.32 mmol). After 18 hours the reaction was evaporated in vacuo, taken up in 25 mL EtOAc and washed successively with 25 mL saturated NaHCO3 then 25 mL brine. The organic phase was dried over Na2SO4, filtered, and evaporated in vacuo to a residue. The residue was purified via silica gel chromatography (30-60% EtOAc/heptane) to give compound 27b as a yellow-tan powder. MS: M+H+=397.0, 1H NMR (d6-DMSO): delta 10.67 (s, 1H), 8.80 (s, 1H), 8.59 (s, 1H), 7.69 (d, 2H), 7.51 (d, 2H), 3.02 (t, 2H), 2.78 (t, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,99368-68-0, its application will become more common.

Reference:
Patent; Codd, Ellen; Dax, Scott L.; Flores, Christopher; Jetter, Michelle; Youngman, Mark; US2006/223837; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 56826-61-0, 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.56826-61-0, name is (2-Methylpyridine-3-yl)methanol, molecular formula is C7H9NO, molecular weight is 123.1525, as common compound, the synthetic route is as follows.

(a) 2-methyinicotinaidehyde: To a stirred solution of (2-methyipyridin-3-yl)methanoi (200 mg, 1.6 mmol) in CH2CI2 (10 mL) was added Mn02 (200 mg, 2.3 mmol). The mixture wasrefluxed overnight under rutrogcn. The solid was removed by fihration. After removal ofsolvent, the crude product was purified by silica gel column chromotography (petroleumether/EtOAc = i/i) to give the title compound (120 rug, 60%) as a colorless liquid .LCMS-PI:122.0 [M+H]t R = 0.344 miii.

Statistics shows that 56826-61-0 is playing an increasingly important role. we look forward to future research findings about (2-Methylpyridine-3-yl)methanol.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; WO2013/19626; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73406-50-5, 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. 73406-50-5, name is Ethyl 3-hydroxypicolinate. A new synthetic method of this compound is introduced below.

The reaction was performed under Ar atmosphere.A solution of ethyl 3-hydroxypicolinate (2.10 g, 12.6 mmol) and ethyl bromoacetate(1.60 mL, 14.4 mmol) in anhydrous acetone (25 mL) was treated with anhydrousK2003,stirred under reflux for 15 h and cooled down to 23 00. The mixture was filteredand the solvent evaporated. The residue was dissolved in CH2CI2 (100 mL), washed with water (3 x 50 mL), dried over anhydrous MgSO4, filtered and evaporated. Column chromatography (SiC2 EtOAc/Heptane 25:75 -> 40:60) gave Ethyl 3-(2-ethoxy-2- oxoethoxy)picolinate (2.42 g, 76%) as a colorless oil.1H NMR (400 MHz, Chloroform-o) 6 = 8.36 (dd, J= 4.5, 1.2 Hz, 1H, H-Ar), 7.39 (dd, J8.5, 4.5 Hz, 1H, H-Ar), 7.29 (dd, J= 8.6, 1.2 Hz, 1H, H-Ar), 4.74 (s, 2H, O-CH2C=O),4.47 (q, J= 7.1 Hz, 2H, O-CH2CH3), 4.27 (q, J= 7.1 Hz, 2H, O-CH2CH3), 1.44 (t, J=7.1 Hz, 3H, O-CH2CH3), 1.29 (t, J= 7.1 Hz, 3H, O-CH2CH3) ppm.MS (ESl+, H20/MeCN) mlz(%): 254.0 (100, [M + H]j.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73406-50-5, Ethyl 3-hydroxypicolinate, and friends who are interested can also refer to it.

Reference:
Patent; EUROPEAN MOLECULAR BIOLOGY LABORATORY; WILL, David William; REID, George; CHARAPITSA, Iryna; LEWIS, Joe David; (187 pag.)WO2018/229193; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 81803-60-3 , The common heterocyclic compound, 81803-60-3, name is Ethyl imidazo[1,5-a]pyridine-3-carboxylate, molecular formula is C10H10N2O2, 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.

Ethyl imidazo[1 ,5-a]pyridine-3-carboxylate (25 mg, 0.13 mmol), (f?)-1-(2-fluorophenyl)- 4,5,6,7-tetrahydro-1 H-indazol-4-amine hydrochloride (S15) (49 mg, 0.18 mmol) and bis(trimethylaluminum)-1 ,4-diazabicyclo[2.2.2]octane adduct (51 mg, 0.20 mmol) were dissolved in THF (2 ml). The reaction mixture was stirred at 60C for 5 h under nitrogen atmosphere. The solvent was removed at reduced pressure and DCM and brine were added. The phases were separated and the organic phase was filtered and concentrated. The mixture was purified by column chromatography eluting with a gradient of EtOAc in hexanes (20-70%) to give the title compound, 31 mg (62%). 1H NMR (400 MHz, CDCI3) delta 9.54 (d, J = 8.2 Hz, 1 H), 7.71 (s, 1 H), 7.57 (d, J = 9.1 Hz, 1 H), 7.53 (d, J = 7.7 Hz, 1 H), 7.48 (td, J = 7.7, 1.7 Hz, 1 H), 7.45 (d, J = 0.7 Hz, 1 H), 7.44-7.37 (m, 1 H), 7.30-7.20 (m, 2H, overlapping with the solvent peak), 6.98 (ddd, J = 9.1 , 6.6, 1.0 Hz, 1 H), 6.85 (ddd, J = 7.2, 6.6, 1.3 Hz, 1 H), 5.43-5.32 (m, 1 H), 2.68-2.49 (m, 2H), 2.22-2.09 (m, 1 H), 2.03-1.82 (m, 3H). m/z (ES+) 376 [M+H]+.

The synthetic route of 81803-60-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LAIN, Sonia; DRUMMOND, Catherine; LEEUWEN, Ingeborg van; HARALDSSON, Martin; JOHANSSON, Lars; SANDBERG, Lars; YNGVE, Ulrika; (126 pag.)WO2017/77280; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1450634-01-1, 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 1450634-01-1 as follows.

To a solution of 3-(prop-1-en-2-yl)picolinonitrile in acetic acid was added 10% Pd/C. The parr shaker bottle was evacuated/H2 purged 3x, and then shaken at Sopsi until starting material was consumed (typically Patent; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore; JIANG, Rong; SONG, Xinyi; WO2013/119639; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 51173-05-8, 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. 51173-05-8, name is 5-Fluoro-2-hydroxypyridine. A new synthetic method of this compound is introduced below.

The solid from above containing (4-80) was divided in 4 batches and treated with H2SO4 and fuming HNO3 as shown below. The amounts used were: Compound 4-80 was dissolved in sulfuric acid (the larger amounts indicated above) at rt and then heated to 65 C. A preformed solution of fuming nitric acid and sulfuric acid (the smaller amount indicated above) was added dropwise. The temperature was kept between 65 C. and 80 C. (rxn is exothermic and although the bath is at 65 C., temperature goes higher, usually 75, sometimes 80 C.). After the addition was complete, the reaction mixture was heated at 65 C. for an additional hr. The reaction mixture was then cooled to rt and poured in a flask containing ice) (20 g of ice/gr compound, evolution of gas occurred). A solid precipitated out and it was collected by filtration (1HNM? showed 4-80 and something else (discarded)). [1493] The aqueous layer was extracted with AcOEt several times (3-5) and concentrated on a rotary evaporator under vacuum to afford a solid that was triturated with ether to afford 5-80 as a bright yellow solid. A total of 117 g of desired product was collected in the first crop (27% yield from diazonium salt). A portion did not crystallize: this oil was triturated with MeOH and Et2O to afford 3.6 g of 5-80; another precipitation from the mother liquid afforded an additional 6.23 g of the desired product 5-80 [1494] Total:117.0+3.6+6.23 =126.83. 30.4%). Yield for 3 steps (decomposition of diazonium salt; deprotection and nitration). [1495] Analytical data from Notebook: 53877-115: 1HNMR(delta, MeOD): 8.56-8.27 (dd, J=7.5, 3.3 Hz, 1H), 8.01 (d, J=3.3 Hz, 1H); LC/MS(M+1)+=158.9; rt=0.15 min. [1496] Note: A portion of the aqueous acidic solution was taken and neutralized with Na2CO3 until effervescence stopped and then it was extracted with AcOEtA different product was obtained. No desired product in these extracts.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,51173-05-8, 5-Fluoro-2-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Wang, Tao; Zhang, Zhongxing; Meanwell, Nicholas A.; Kadow, John F.; Yin, Zhiwei; Xue, Qiufen May; Regueiro-Ren, Alicia; Matiskella, John D.; Ueda, Yasutsugu; US2004/110785; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem