반응 #170439

반응 방정식

water

trimethylaluminium

isopropylamine

6-(3-phenyl-5-trifluoromethyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

→

title compound

수율 96.8%

N-Isopropyl-6-(3-phenyl-5-trifluoromethyl-isoxazol-4-ylmethoxy)-nicotinamide

수율 96.8%

용매

dioxane

dioxane

반응 조건

후처리

1. 1
   온도The resulting mixture was then heated at 85-95° C. for 5 h
2. 2
   온도cooled to room temperature
3. 3
   추출extracted with ethyl acetate which
4. 4
   세척was then washed with brine
5. 5
   건조dried over sodium sulfate
6. 6
   기타evaporated
7. 7
   기타Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1)

실험 절차

A solution of trimethylaluminium (2 M in toluene, 529 μL, 1.1 mmol) was added dropwise (exothermic) to a solution of isopropylamine (63 mg, 91 μL, 1.1 mmol) in dioxane (7 mL) and the resulting mixture was stirred at room temperature for 1 h. Then a solution of 6-(3-phenyl-5-trifluoromethyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (100 mg, 0.26 mmol) in dioxane (4 mL) was added. The resulting mixture was then heated at 85-95° C. for 5 h and then cooled to room temperature and then poured into water and extracted with ethyl acetate which was then washed with brine, dried over sodium sulfate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (102 mg, 95%) which was obtained as a white solid. MS: m/e=406.4 [M+H]+.

출처