Category: 93349-99-6

Reference of 93349-99-6, 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. 93349-99-6, name is Methyl 5-bromo-6-methoxynicotinate, molecular formula is C8H8BrNO3, 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.

Methyl 5-bromo-6-methoxynicotinate (1 g),Ethynyltriisopropylsilane (1.5 ml),Bis (triphenylphosphine) dichloropalladium (280 mg),Copper (I) iodide (80 mg),Triethylamine (1.6 ml), And acetonitrile (15 ml)And the mixture was stirred overnight at 80 C. under a nitrogen atmosphere.The mixture was cooled to room temperature and extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine,Dried over magnesium sulfate and then concentrated under reduced pressure. THF (15 ml) and 1 M tetrabutylammonium fluoride THF solution (8 ml) were added to the obtained residue, and the mixture was stirred at room temperature for 1 hour. The mixture was extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane / ethyl acetate) to give the title compound (0.55 g)

According to the analysis of related databases, 93349-99-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; MIZOJIRI, RYO; CARY, DOUGLAS ROBERT; HIRAYAMA, TAKAHARU; ITO, MASAHIRO; TANAKA, TOSHIO; IMAEDA, YASUHIRO; SASAKI, SHIGEKAZU; TAKAMI, KAZUAKI; FUKUDA, KOICHIRO; KAMAURA, MASAHIRO; MORISHITA, NAO; (133 pag.)JP2017/222626; (2017); A;,
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. 93349-99-6, name is Methyl 5-bromo-6-methoxynicotinate. A new synthetic method of this compound is introduced below., Product Details of 93349-99-6

26B: A mixture of 1A (378 mg, 0.915 mmol), bis(pinacolato)diboron (290 mg,1.143 mmol), potassium acetate (269 mg, 2.74 mmol) and PdC12(dppf)-CH2C12 adduct (37.3 mg, 0.046 mmol) in dioxane (4 mL) was heated at 100 C for 60 mm. After cooling to rt, methyl 5-bromo-6-methoxynicotinate (154 mg, 0.625 mmol) and1,1 ?-bis(di-tert-butylphosphino)ferrocenepalladium dichloride (19.39 mg, 0.030 mmol) were added and the mixture degassed by nitrogen sparge for 5 mm. 2M K3P04 (aq) (0.892 mL, 1.785 mmol) was quickly added and the reaction mixture heated at 100 C for 15 mm. The reaction mixture was cooled to rt and volatiles removed in vacuo. The crude residue was loaded onto a 40g ISCO column and purified by flash chromatography,eluting with 0-100% EtOAc in hexanes. Afforded product (301 mg, 0.572 mmol, 96 % yield) as a crystalline beige solid.MS ESI m/z 499.9 (M+H)

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Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUO, Junqing; HART, Amy, C.; MACOR, John, E.; MERTZMAN, Michael, E.; PITTS, William, J.; SPERGEL, Steven, H.; WATTERSON, Scott, Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; CHEN, Jie; DZIERBA, Carolyn, Diane; LUO, Guanglin; SHI, Jianliang; SIT, Sing-Yuen; (428 pag.)WO2018/148626; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem