Category: 884494-52-4

Electric Literature of 884494-52-4, 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. 884494-52-4, name is 3-Bromo-2-fluoro-4-iodopyridine. A new synthetic method of this compound is introduced below.

In a dry 3 neck 2 L flask equipped with a dry addition funnel, thermometer and stir bar was added 3- bromo-2-fluoro-4-iodopyridine (83.4 g, 276 mmol) followed by 300 mL of anhydrous THF under an atmosphere of nitrogen. The solution was cooled to -7O0C in 2-propanol/dry ice bath. A solution of isopropylmagnesium chloride 2.0 M in diethyl ether (145 mL, 290 mmol) was added drop wise over a period of 30 minutes. The solution was then stirred for 30 minutes before zinc (II) chloride 0.5 M in THF (276 mL, 138 mmol) was cannulated in. The solution was warmed to room temperature and stirred for lhour. The addition funnel was replaced with a reflux condenser and N4-cyclopentyl-5-iodopyrimidine-2,4-diamine (243, see example 200) (28.00 g, 92.1 mmol) was added, followed by Pd(PPh3)4 (5.32 g, 4.60 mmol). The solution was heated over night at a gentle reflux. After concentrating the solution to 1/1 Oth of the volume under vacuum, it was cooled in an ice bath. To this was added 100 mL of cold saturated NH4Cl, followed by 500 mL of water. 50OmL of 12% isopropanol/DCM was then added and the solution was stirred at room temperature for lhour before being filtered through filter paper. The filter cake was washed in succession with water, DCM and 12% 2-propanol /DCM. The filtrate was partitioned in a separation runnel and the aqueous layer was washed with 12% 2-propanol /DCM. The organics were dried over MgSO4 and then concentrated under vacuum. The residue obtained was partially dissolved in DCM with sonication and filtered off to give compound 244 (26.45g, 81.6%) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) delta ppm 8.18 (1 H, d, J= 4.9 Hz), 7.52 (1 H, s), 7.26 (1 H, dd, J= 4.9, 0.7 Hz), 6.34 (2 H, s), 6.12 (1 H, d, J= 7.6 Hz), 4.42 (1 H, sxt, J= 7.4 Hz), 1.76 – 1.96 (2 H, m), 1.55 – 1.68 (2 H, m), 1.31 – 1.53 (4 H, m) ) ppm; LCMS-ESI (POS), M/Z, M+l : Found 352.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884494-52-4, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2009/85185; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 884494-52-4, name is 3-Bromo-2-fluoro-4-iodopyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-2-fluoro-4-iodopyridine

Isopropylmagnesium chloride, 2 M solution in THF (0.814 mL, 1.63 mmol) was added dropwise over 15 minutes to a degassed solution of 3-bromo-2-fluoro-4-iodopyridine (0.468 g, 1.55 mmol) in Et2O (0.150 mL) and THF (0.850) cooled at -78 0C. The solution was stirred for 0.5 h. Zinc chloride, 1.0 M solution in diethyl ether (0.776 mL, 0.776 mmol) was then added dropwise to the reaction over 10 minutes. The reaction was allowed to reach room temperature. The reaction warmed to room temperature within 15 min. A solution of compound 238 (0.150 g, 0.517 mmol) and tetrakis(triphenylphosphine)palladium (0.0418 g, 0.0362 mmol) in THF (0.50 mL) was added to the reaction. The reaction was equipped with a reflux condenser and stirred in a 60 0C oil bath. After 2 h the reaction was removed from heat and allowed to stand overnight. Saturated NH4Cl (0.5 mL) and 12% 2-propanol in CH2Cl2 (2 mL) were added. The organics were sequestered and the aqueous was extracted with 12% 2- propanol in CH2Cl2 (4 x 4 mL). The combined organics were washed with brine, dried over MgSO4, and concentrated in vacuo. Silica gel chromatography (elution 3% methanol in DCM with 0.175 % NH4OH additive) afforded compound 240 (0.140 g, 80.1% yield). 1H NMR (500 MHz, CDCl3) delta ppm 0.22 (d, J= 4.40 Hz, 2 H) 0.46 – 0.59 (m, 2 H) 0.96 – 1.07 (m, 1 H) 3.21 – 3.36 (m, 2 H) 4.51 (br. s., 1 H) 5.11 (br. s., 2 H) 7.16 (d, J= 4.89 Hz, 1 H) 7.69 (s, 1 H) 8.22 (d, J= 4.89 Hz, 1 H) ppm.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 884494-52-4, 3-Bromo-2-fluoro-4-iodopyridine.

Reference:
Patent; AMGEN INC.; WO2009/85185; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 884494-52-4, name is 3-Bromo-2-fluoro-4-iodopyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-2-fluoro-4-iodopyridine

Isopropylmagnesium chloride, 2 M solution in THF (0.814 mL, 1.63 mmol) was added dropwise over 15 minutes to a degassed solution of 3-bromo-2-fluoro-4-iodopyridine (0.468 g, 1.55 mmol) in Et2O (0.150 mL) and THF (0.850) cooled at -78 0C. The solution was stirred for 0.5 h. Zinc chloride, 1.0 M solution in diethyl ether (0.776 mL, 0.776 mmol) was then added dropwise to the reaction over 10 minutes. The reaction was allowed to reach room temperature. The reaction warmed to room temperature within 15 min. A solution of compound 238 (0.150 g, 0.517 mmol) and tetrakis(triphenylphosphine)palladium (0.0418 g, 0.0362 mmol) in THF (0.50 mL) was added to the reaction. The reaction was equipped with a reflux condenser and stirred in a 60 0C oil bath. After 2 h the reaction was removed from heat and allowed to stand overnight. Saturated NH4Cl (0.5 mL) and 12% 2-propanol in CH2Cl2 (2 mL) were added. The organics were sequestered and the aqueous was extracted with 12% 2- propanol in CH2Cl2 (4 x 4 mL). The combined organics were washed with brine, dried over MgSO4, and concentrated in vacuo. Silica gel chromatography (elution 3% methanol in DCM with 0.175 % NH4OH additive) afforded compound 240 (0.140 g, 80.1% yield). 1H NMR (500 MHz, CDCl3) delta ppm 0.22 (d, J= 4.40 Hz, 2 H) 0.46 – 0.59 (m, 2 H) 0.96 – 1.07 (m, 1 H) 3.21 – 3.36 (m, 2 H) 4.51 (br. s., 1 H) 5.11 (br. s., 2 H) 7.16 (d, J= 4.89 Hz, 1 H) 7.69 (s, 1 H) 8.22 (d, J= 4.89 Hz, 1 H) ppm.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 884494-52-4, 3-Bromo-2-fluoro-4-iodopyridine.

Reference:
Patent; AMGEN INC.; WO2009/85185; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem