반응 #993383

반응 방정식

Methyl 4-cyano-5-iodo-2-(trifluoromethyl)benzoate

XANTPHOS

cesium carbonate

(R)-sec-butylamine

→

(R)-methyl 5-(sec-butylamino)-4-cyano-2-(trifluoromethyl)benzoate

수율 31.0%

용매

dioxane

반응 조건

후처리

1. 1
   기타was sparged with nitrogen for 15 minutes
2. 2
   온도The reaction mixture was cooled to ambient temperature
3. 3
   여과was filtered through celite
4. 4
   세척The filter cake was washed with ethyl acetate
5. 5
   농축the filtrate was concentrated
6. 6
   기타to afford an orange oil which
7. 7
   기타was purified by column chromatography (silica gel, 5-15% ethyl acetate in hexanes)

실험 절차

Methyl 4-cyano-5-iodo-2-(trifluoromethyl)benzoate (174 mg, 0.49 mmol) was dissolved in dioxane (2 mL) and was sparged with nitrogen for 15 minutes. XANTPHOS (57 mg, 0.098 mmol), cesium carbonate (350 mg, 1.07 mmol), (R)-sec-butylamine (0.1 mL, 0.986 mmol), and tris(dibenzylideneacetone)dipalladium (45 mg, 0.049 mmol) were added, and the mixture was stirred in a sealed tube at 95° C. for 20 h. The reaction mixture was cooled to ambient temperature and was filtered through celite. The filter cake was washed with ethyl acetate and the filtrate was concentrated to afford an orange oil which was purified by column chromatography (silica gel, 5-15% ethyl acetate in hexanes) to afford (R)-methyl 5-(sec-butylamino)-4-cyano-2-(trifluoromethyl)benzoate (45 mg, 0.150 mmol, 31% yield) as a yellow oil. GCMS for C14H15F3N2O2: 300 (M+).

출처