PHENYLPYRIDYLMETHYL ACETATE synthesis

7synthesis methods

Product Name:PHENYLPYRIDYLMETHYL ACETATE
CAS Number:26483-64-7
Molecular formula:C14H13NO2
Molecular Weight:227.26

7251-52-7

2-Pyridineacetamide, N-(cyclopropylmethyl)-α-phenyl-

334932-80-8

26483-64-7

d) (RS)-phenyl-(2-pyridyl)acetamide (0.340 g, 1.60 mmol) was dissolved in 5 mL of saturated HCl/methanol solution and placed in a closed vessel at reflux for 6 hours. Upon completion of the reaction, the mixture was poured onto 25 g of ice and the pH was adjusted to 8-9 by slowly adding 28% sodium hydroxide solution, keeping the temperature below 10 °C during the process. The product was extracted with a solvent mixture of ethyl acetate/water and the organic phase was dried over anhydrous magnesium sulfate and concentrated. The crude product was purified by rapid chromatography on silica gel, using ethyl acetate and hexane (1:4, v/v) as eluent to give 0.204 g (0.939 mmol, 59% yield) of (RS)-2-phenyl-2-(pyridin-2-yl)acetic acid methyl ester as a white solid, melting point 74 °C, mass spectrum (MS): m/e = 228.2 ([M+H]+).

1658-42-0 Synthesis

1658-42-0
181 suppliers
$11.00/1g

108-86-1 Synthesis

108-86-1
525 suppliers
$10.00/5g

26483-64-7
27 suppliers
$108.00/100mg

Yield:26483-64-7 97%

Reaction Conditions:

with palladium diacetate;caesium carbonate;XPhos in 1,4-dioxane at 100; for 12 h;Inert atmosphere;Schlenk technique;

Steps:

1.2 General procedure for the arylation reaction

General procedure: An oven-dried Schlenk tube was charged with Pd(OAc)2 (0.015 mmol, 3.4 mg), X-Phos (0.015 mmol, 7.2 mg), Cs2CO3 (0.9 mmol, 293 mg), substrate 1 (0.3 mmol) and 2 (0.4 mmol). The reaction vessel was evacuated and backfilled again with nitrogen gas, and 1,4-dioxane (1 mL) was added via syringe under nitrogen. The reaction mixture was stirred at 100 °C for 12 hours. The reaction mixture was then cooled to room temperature and diluted with EtOAc. The crude was nextfiltered through a plug of celite, which was washed with ethyl acetate. The solution was concentrated and further purifiedby flash column chromatography to afford the corresponding product.

References:

Jin, Chaochao;Xu, Kun;Fan, Xiao;Liu, Changyao;Tan, Jiajing [Chinese Chemical Letters,2020,vol. 31,# 1,p. 91 - 94] Location in patent:supporting information

67-56-1 Synthesis