反応 #694110

反応方程式

tetrabutylammonium fluoride

3-iodofluorobenzene

5-trimethylsilanylethynyl-nicotinic acid ethyl ester

→

title compound

収率 80.0%

5-(3-Fluorophenylethynyl)-nicotinic acid ethyl ester

収率 80.0%

溶媒

tetrahydrofuran

ethyl acetate

反応条件

後処理

1. 1
   洗浄Wash with an aqueous saturated solution of ammonium chloride
2. 2
   乾燥dry (magnesium sulfate)
3. 3
   ろ過filter
4. 4
   濃縮concentrate
5. 5
   その他Purify the residue by silica gel chromatography
6. 6
   洗浄eluting with 2.5:45:52.5 ethyl acetate

実験手順

Add a 1 M solution of tetrabutylammonium fluoride (0.88 g, 3.38 mmol) in tetrahydrofuran to a mixture of 3-iodofluorobenzene (0.50 g, 2.25 mmol), 5-trimethylsilanylethynyl-nicotinic acid ethyl ester, (prepared as described in PREPARATION 16), (0.84 g, 3.38 mmol), bis(triphenylphosphine)palladium (II) dichloride (0.03 g, 0.05 mmol) and copper (I) iodide (0.02 g, 0.09 mmol) at −78° C. Warm to room temperature, stir overnight and then dilute with ethyl acetate. Wash with an aqueous saturated solution of ammonium chloride, dry (magnesium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with 2.5:45:52.5 ethyl acetate:chloroform:hexanes, to give the title compound as a pale yellow solid (0.46 mg, 80%).

出典