Tag: M.W:200-300

Reference of 863704-60-3, 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.863704-60-3, name is 6-(4-Fluorophenyl)picolinic acid, molecular formula is C12H8FNO2, molecular weight is 217.2, as common compound, the synthetic route is as follows.

A mixture of Intermediate 3-07 (156 mg, 0.72 mmol), HATU (394 mg, 1.0 mmol) and DIPEA (0.639 mL, 3.66 mmol) in DCM (6 mL) was stirred at RT for 15 min. A solution of Intermediate 3-04 (155 mg, 0.72 mmol) in DCM (4 mL) was added and the reaction mixture was stirred at RT for 14 h. The mixture was washed with water, and the organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (Biotage, cHex:EtOAc, 85:15 to 50:50) to afford Intermediate 3-09 (298 mg, 100%).

Statistics shows that 863704-60-3 is playing an increasingly important role. we look forward to future research findings about 6-(4-Fluorophenyl)picolinic acid.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; ALVAREZ ESCOBAR, Rosa Maria; GARCIA GARCIA, Ana Belen; RIESCO FAGUNDO, Rosario Concepcion; BLANCO APARICIO, Carmen; WO2012/98387; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 915006-52-9, 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.915006-52-9, name is 6-Bromo-2-iodopyridin-3-amine, molecular formula is C5H4BrIN2, molecular weight is 298.91, as common compound, the synthetic route is as follows.

To a mixture of 6-bromo-2-iodopyridin-3-amine (100 mg, 0.34 mmol), 1,2-dimethoxy-4-(prop-1-yn-1-yl)benzene (74 mg, 0.42 mmol), lithium chloride (18 mg, 0.42 mmol), sodium carbonate (180 mg, 1.68 mmol) and Pd(dppf)Cl2 (12.5 mg, 0.017 mmol) in a screw cap vial was added DMF (2 mL). The vial was fitted with a Teflon-lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 100 C. for 16 h. LCMS analysis shows formation of two isomers, in approximately 3:1 ratio. 1H NMR analysis suggested the major product to be 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (5A-1). The reaction mixture was diluted with EtOAc (50 mL), poured into a separatory funnel and washed with 10% aqueous LiCl solution (2*10 mL) and saturated aqueous NaCl solution (10 mL), dried (Na2SO4), filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM and purified on a silica gel column chromatography with a 15 min gradient from 0%-100% DCM/EtOAc to afford 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) that was contaminated with Intermediate 5A-2, 5-bromo-3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine, m/z (303, M+1), 80 mg (67%). To a mixture containing 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) and Intermediate 5A-2 (100 mg, 0.29 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (111 mg, 0.36 mmol), and Pd(dppf)C12 (10.5 mg, 0.014 mmol) in a screw cap vial was added THF (2.5 mL) followed by 3M aqueous solution of tripotassium phosphate (0.10 mL, 0.3 mmol). The vial was fitted with a Teflon lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 75 C. for 3 h. The reaction mixture was cooled to room temperature and treated with saturated aqueous NaCl solution (5 mL) and extracted with ethyl acetate (3*10 mL). The extracts were combined, dried (Na2SO4), filtered and concentrated. The crude product was dissolved in a small amount of DCM and purified on silica gel column chromatography eluting with a 10 min gradient from 5%-100% DCM/EtOAc. No separation was observed. A mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5B) and the regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1 (2H)-carboxylate was isolated (100 mg, 77% yield), m/z (550, M+1) and was used as such in subsequent step. A mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5B) and regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (95 mg, 0.21 mmol) was dissolved in MeOH (5 mL) and transferred to a Parr bottle. The mixture was purged with nitrogen. Pearlman’s Catalyst (25 mg, 0.036 mmol) was added and the bottle was pressurized with hydrogen gas (50 psi) and shaken for 22 h. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated. The resulting residue was dissolved in a small amount of DCM and charged to a silica gel column, which was eluted over a 10 min gradient with 1%-5% MeOH/DCM to afford a mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5C) and the regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (82 mg, 80%), m/z (452, M+H). The mixture of isomers (tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)piperidine-1-carboxylate (Intermediate 5C) and tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)piperidine-1-carboxylate (80 mg, 0.18 mmol) were suspended in 4 N HCl in dioxane (4 mL, 16.00 mmol), stirred for 30 min, and concentrated to dryness. The resulting residue was suspended in diethyl ether (1 mL) and the solids were filtered and dried to give a mixture of 2-(3,4-dimethoxyphenyl)-3-methyl-5-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine (Intermediate 5D) and 3-(3,4-dimethoxyphenyl)-2-methyl-5-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine as bis HCl salts (50 mg, 65%), m/z (352, M+H). To a solution containing a mixture of 3-(3,4-dimethoxyphenyl)-2-methyl-5-(piperidin-4-yl)-1H-pyrrolo[2,3-c]pyridine 2 HCl (Intermediate 5D) and 2-(3,4-dimethoxyphenyl)-3-methyl-5-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine, 2 HCl (30 mg, 0.07 mmol) in DMF (1 mL) was added 1-isobu…

Statistics shows that 915006-52-9 is playing an increasingly important role. we look forward to future research findings about 6-Bromo-2-iodopyridin-3-amine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Dyckman, Alaric J.; Dodd, Dharmpal S.; Mussari, Christopher P.; Sherwood, Trevor C.; Whiteley, Brian K.; Gilmore, John L.; Kumar, Sreekantha Ratna; Pasunoori, Laxman; Srinivas, Pitani Veera Venkata; Duraisamy, Srinivasan Kunchithapatham; Hegde, Subramanya; Anumula, Rushith Kumar; US2019/185469; (2019); 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. 77837-09-3, name is Methyl 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate, the common compound, a new synthetic route is introduced below. HPLC of Formula: C13H11NO3

Step 3; 6-Oxo-l -phenyl- 1 ,6-dihydropyridine-3-carboxylic acid:; Lithium hydroxide monohydrate (0.366 g, 8.73 mmol) was added to a mixture of methyl-6-oxo-l -phenyl- 1,6- dihydropyridine-3-carboxylate (1.0 g, 4.37 mmol), tetrahydrofuran (9 mL) and water (6 mL) at 0 °C. The mixture was stirred for 1 hour, diluted with water and washed with ethyl acetate. The pH of the aqueous layer was adjusted to 2 using 2 N hydrochloric acid and the precipitate was filtered to give the title compound as a brown solid (0.740 g, 79percent). m.p. 256-263 °C; *H NMR (400 MHz, DMSO-d6) delta 6.53 (d, / = 9.4 Hz, 1H), 7.40-7.49 (m, 5H), 7.87 (dd, / = 2.5, 9.8 Hz , 1H), 8.23 (d, / = 2.5 Hz, 1H); IR (KBr) upsilon 3446, 1708, 1645, 1577, 1263, 1228 cm”1; MS 214 (M – 1).

The synthetic route of 77837-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; ZHANG, Chengzhi; SOMMERS, Andreas; WO2012/122165; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109613-97-0, Adding some certain compound to certain chemical reactions, such as: 109613-97-0, name is 2-Bromo-4-methoxypyridin-3-amine,molecular formula is C6H7BrN2O, 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 109613-97-0.

To an ice-cold solution of 2-bromo-4-methoxypyridin-3-amine (Intermediate 38), (2.74 g) in pyridine (102 mL) was added ethyl chloroformate (1.91 mL) dropwise and then stirred at rt for 45 min. The reaction mixture was cooled in an ice-bath and more ethyl chloroformate (9 mL) added and the mixture left to stir overnight at rt. The reaction mixture was diluted with EtOAc and washed with sat. aq. NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers washed with brine, dried over MgSO4, filtered and evaporated under vacuum to give a solid. Product was observed in the aqueous layer by LC-MS, so this was re-extracted with EtOAc (3*) and evaporated under vacuum to give a solid which was combined with the previous solid, dissolved in DCM and purified by column chromatography (normal phase, 50 g, Biotage SNAP cartridge KP-Sil, 50 mL/min, gradient 10-70% EtOAc in n-hexane) to give the desired product (2.35 g). LCMS: m/z 275.43 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.32 (t, J=7.1 Hz, 3H) 3.93 (s, 3H) 4.24 (q, J=7.1 Hz, 2H) 6.06 (br. s., 1H) 6.86 (d, J=5.6 Hz, 1H) 8.19 (d, J=5.6 Hz, 1H)

According to the analysis of related databases, 109613-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; PAYNE, Andrew; CASTRO PINEIRO, Jose Luis; BIRCH, Louise Michelle; KHAN, Afzal; BRAUNTON, Alan James; KITULAGODA, James Edward; SOEJIMA, Motohiro; WO2015/49574; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211521-46-8, 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. 1211521-46-8, name is 2-Bromo-4-chloro-3-methylpyridine, molecular formula is C6H5BrClN, 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.

A solution of 2-bromo-3-methyl-4-chloro-pyridine (10.6 g, 57.1 mmol) in freshly distilled THF (120 mL) was cooled down to 0C and treated with isopropyl magnesium chloride (45.7 mL, 2.0 M in THF, 91.5 mmol). The resulting mixture was stirred at room temperature for 3 h then cooled to -5C. Cyclopropane carboxaldehyde (6.83 mL, 91.5 mmol) was added. The reaction mixture was stirred at room temperature for 1 h and quenched by adding water (100 mL), and extracted with ethyl acetate (2X150 mL). The organic phase was separated, dried, and concentrated. The residue was purified by flash silica column chromatography (hexane:ethyl acetate, 3:1) to afford the title compound as a yellow oil (7.01 g, 62%). ESI-MS m/z: 198 (M+H)+; 1H NMR (CDCl3, 300 MHz) delta ppm: 8.28 (d, J = 5.4 Hz, 1 H), 7.26 (d, J = 5.4 Hz, 1 H), 4.79 (d, J = 5.4 Hz, 1 H), 4.55 (br, s, 1 H), 2.39 (s, 3 H), 1.10-1.28 (m, 1 H), 0.58-0.41 (m, 4 H).

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 1211521-46-8, 2-Bromo-4-chloro-3-methylpyridine.

Reference:
Patent; Emergent Product Development Gaithersburg Inc.; Roussel, Patrick; Heim, Jutta; Schneider, Peter; Bartels, Christian; Liu, Yaoquan; Dale, Glenn; Milligan, Daniel; (107 pag.)EP3034078; (2016); 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. 61830-40-8, name is 3,5-Dibromopicolinic acid, molecular formula is C6H3Br2NO2, 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. Computed Properties of C6H3Br2NO2

To n-butyllithium (2.5 M in hexane, 12 mL, 30 mmol) in THF (40 mL) at -78 C was added a solution of 3,5-dibromopicolinic acid (4.0 g, 14 mmol) in THF (60 mL) over 30 minutes. The reaction was stirred at -78 C for 1 hour after which DMF (11 mL, 144 mmol) was added dropwise. The cold bath was allowed to expire while stirring for 12 h. Water was added followed by IN HC1 (30 mL). The pH was adjusted to pH 3-4 using IN NaOH. The solution was extracted with EtOAc while maintaining a pH of 3 to 4. The combined organic layerswere washed with water and brine, dried (MgS04), filtered, and concentrated in vacuo to provide the title compound Ab2 that was carried on directly.

With the rapid development of chemical substances, we look forward to future research findings about 61830-40-8.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GILBERT, Eric, J.; CUMMING, Jared, N.; SCOTT, Jack, D.; WU, Wen-Lian; BURNETT, Duane, A.; STAMFORD, Andrew, W.; WO2014/150344; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 936011-17-5, 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. 936011-17-5, name is 5-Bromo-2-methoxyisonicotinaldehyde, molecular formula is C7H6BrNO2, 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.

A mixture of 5-bromo-2-methoxypyridine-4-carbaldehyde (430 mg, 1.99 mmol), 4-(tributylstannyl)-1-(triphenylmethyl)-1H-imidazole (Intermediate A, 1800 mg, 3.0 mmol) and PdAMPHOS (142 mg, 0.20 mmol) in acetonitrile (20 mL) was stirred at 100 C. for 8 h under N2 atmosphere. The resulting reaction mixture was diluted with water (40 mL) and extracted with ethyl acetate (80 mL*2). The combined organic phase was washed with brine, and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with petroleum ether: ethyl acetate (7:3) to yield 2-methoxy-5-[1-(triphenylmethyl)-1H-imidazol-4-yl]pyridine-4-carbaldehyde (630 mg, 71%) as yellow solid. MS: m/z=446.0 [M+H]+.

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 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; (167 pag.)US2016/75711; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 77199-09-8, Adding some certain compound to certain chemical reactions, such as: 77199-09-8, name is Ethyl 5-bromopicolinate,molecular formula is C8H8BrNO2, 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 77199-09-8.

Under the protection of N2, PdCl2(dppf) (1.80 g, 0.0025 mol) was added to an anhydrous 1,4-dioxane (200 mL) solution of ethyl 5-bromo-2-picolinate (10.00 g, 0.043 mol), bis(pinacolato)diboron (12.20 g, 0.048 mol) and anhydrous potassium acetate (13.00 g, 0.13 mol), and the resulting mixture was heated to 100 C to react overnight. After cooling and concentration under reduced pressure, water and ethyl acetate were added to the residue, stirred for 15 min, and filtered through Celite, and the Celite was rinsed with ethyl acetate. After the filtrate was layered, the aqueous phase was extracted with ethyl acetate once. The ethyl acetate phases were combined, washed with a saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate, and concentrated to obtain a black residue, which was separated through a silica gel column (ethyl acetate/petroleum ether=1:10-1:2) to obtain a white solid product (9.03 g, 75%). 1H NMR (400 MHz, CDCl3,) delta 9.06 (d, J=1.6 Hz, 1H), 8.21 (dd, J=7.6 Hz, J=1.6 Hz, 1H), 8.10 (d, J=7.6 Hz, 1H), 4.48 (q, J=7.2 Hz, 2H), 1.45 (t, J=7.2 Hz, 3H), 1.37 (s, 12H).

According to the analysis of related databases, 77199-09-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; LI, Jijun; WU, Wei; ZHU, Yan; WANG, Huting; ZHAO, Lijia; HE, Weinan; SUN, Yinghui; PENG, Yong; HAN, Yongxin; (108 pag.)EP3412669; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.109306-86-7, name is 2-(2-Bromophenyl)pyridine, molecular formula is C11H8BrN, molecular weight is 234.09, as common compound, the synthetic route is as follows.Application In Synthesis of 2-(2-Bromophenyl)pyridine

Compound 152-3 6.3g (26.86mmol) and sodium azide 3.49 g (53.72mmol), palladium acetate 904mg (4.24mmol),Cerium (IV) sulfate, 17.8g (53.72mmol), Iron (II) chloride 871mg (5.66mmol) was dissolved in 100mL DMSO and stirred at 100C for 79 hours. After the reaction was completed, extracted with ethyl acetate and H2O, separation and purification by column chromatography using Hex / EA to give the title compound 152-2 2.9g (43%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,109306-86-7, 2-(2-Bromophenyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; HEESUNG MATERIAL CO., LTD; KIM, JI-HEE; KIM, YOUNG WOO; LEE, JIN WOO; UHM, SONG JIN; LEE, JU DONG; (45 pag.)KR2015/74833; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 912934-77-1, 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. 912934-77-1, name is 6-Bromopyridine-2-sulfonyl chloride, molecular formula is C5H3BrClNO2S, 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.

To a solution of Compound 12 (0.079 g, 0.780 mmol) and TEA (0.24 mL, 1.715 mmol) in DCM (5 mL) cooled to 0 C was added Compound 11 (0.20 g, 0.780 mmol). The mixturewas stirred at 0 C for 1 h, quenched with water and extracted with DCM. The organic extracts were dried over Mg504 and concentrated to give Compound 13 as an orange oil that was used in subsequent steps without purification (0.21 g, yield 84%): LC/MS: nz/z= 322.8 [M+Hf (Calc: 321.2).

According to the analysis of related databases, 912934-77-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PURDUE PHARMA L.P.; TAFESSE, Laykea; PARK, Jae, Hyun; WO2015/123398; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem