Triethylamine → HCID 86682992, compound

Participants

Reaction Steps

To a stirred solution of 4-chloro-2-iodo-phenylamine (5 g, 19.73 mmol) in THF (40 ml) was added triethyl amine (6.836 ml, 49.32 mmol), and ethynyl-trimethyl-silane (5.576 ml, 39.45 mmol) at 25° C. The mixture was purged with argon for 10 min, followed by the addition of PdCl2(PPh3)2 (0.692 g, 0.99 mmol) and CuI (113 mg, 0.59 mmol) at 25° C. The reaction mixture was stirred at room temperature for 2 h and was subsequently diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford a crude residue which was purified by flash column chromatography (2-5% ethyl acetate in hexane) to afford 4-chloro-2-trimethylsilanylethynyl-phenylamine (3.6 g, 82%) as a brown solid. GC-MS: 223 (M).

Provenance & Evidence