反应详情

Add triethylamine (5 mL) to a stirring mixture of 3-iodopyridine (1.03 g, 5.03 mmol), bis(triphenylphosphine)palladium (II) dichloride (176 mg, 0.252 mmol), copper (I) iodide (96 mg, 0.503 mmol), and 3-trimethylsilanylethynylbenzonitrile, (prepared essentially as described in PREPARATION 5), (1.0 g, 5.03 mmol) at −78° C. After about 3 min, add a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (5.03 mL, 5.03 mmol) in one portion, warm to room temperature and stir overnight. Filter the reaction mixture through fluted filter paper and concentrate. Dissolve the residue in ethyl acetate, wash sequentially with a saturated solution of aqueous sodium bicarbonate, a saturated solution of aqueous sodium chloride, dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 40:60 ethyl acetate:hexanes, followed by a second silica gel chromatography, eluting with 0:100 to 40:60 ethyl acetate:dichloromethane), to give the title product as a yellow solid (730 mg, 71%).

1. custom(prepared essentially
2. customas described in PREPARATION 5), (1.0 g, 5.03 mmol) at −78° C
3. filtrationFilter the reaction mixture through fluted filter paper
4. concentrationconcentrate
5. dissolutionDissolve the residue in ethyl acetate
6. washwash sequentially with a saturated solution of aqueous sodium bicarbonate
7. dry with materiala saturated solution of aqueous sodium chloride, dry (sodium sulfate)
8. filtrationfilter
9. concentrationconcentrate
10. custompurify (silica gel chromatography
11. washeluting with 0:100 to 40:60 ethyl acetate
12. washeluting with 0:100 to 40:60 ethyl acetate