反应 #7903

反应方程式

(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

收率 81.0%

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

收率 81.0%

溶剂

tetrahydrofuran

diethyl ether

反应条件

后处理

1. 1
   温度was heated
2. 2
   温度to reflux for 15 h
3. 3
   洗涤washed with saturated ammonium chloride solution and brine
4. 4
   其他The organic layer was separated
5. 5
   干燥dried with sodium sulfate
6. 6
   过滤filtered
7. 7
   浓缩concentrated
8. 8
   其他Purification by medium pressure liquid chromatography on silica gel (1:5 ethyl acetate/hexanes)

实验过程

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)+.

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