반응 #7903

반응 방정식

(S)-2-[5-bromo-2-oxo-3-(4-trifluoromethylbenzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid methyl ester

(S)-2-[5-Bromo-2-oxo-3-(4-trifluoromethylbenzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid methyl ester

1-naphthyleneboronic acid

cesium fluoride

→

title compound

수율 81.0%

(S)-2-[5-Naphthalen-1-yl-2-oxo-3-(4-trifluoromethylbenzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid methyl ester

수율 81.0%

용매

tetrahydrofuran

diethyl ether

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도to reflux for 15 h
3. 3
   세척washed with saturated ammonium chloride solution and brine
4. 4
   기타The organic layer was separated
5. 5
   건조dried with sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타Purification by medium pressure liquid chromatography on silica gel (1:5 ethyl acetate/hexanes)

실험 절차

A mixture of (S)-2-[5-bromo-2-oxo-3-(4-trifluoromethylbenzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid methyl ester from Step E (66.8 mg, 0.128 mmol), 1-naphthyleneboronic acid (44.0 mg, 0.256 mmol), cesium fluoride (97 mg, 0.64 mmol), tris(dibenzylideneacetone)dipalladium(0) chloroform complex (13.0 mg, 0.013 mmol) and bis(tri-t-butylphosphine)palladium(0) (16.0 mg, 0.031 mmol) in tetrahydrofuran (2.0 mL) was heated to reflux for 15 h. The reaction mixture was cooled to room temperature, diluted with diethyl ether (100 mL), washed with saturated ammonium chloride solution and brine. The organic layer was separated, dried with sodium sulfate, filtered and concentrated. Purification by medium pressure liquid chromatography on silica gel (1:5 ethyl acetate/hexanes) gave 59 mg (81%) of the title compound as a semisolid. MS 571.2 (M+H)+.

출처