Diethyl Ether → 5-Bromo-3-[(trimethylsilyl)ethynyl]pyridin-2-amine

Participants

Reaction Steps

2-amino-5-bromo-3-iodopyridine (105.28 g, 0.3522 mol), CuI (0.6708 g, 3.522 mmol) and PdCl2(PPh3)2 (2.472 g, 3.522 mmol) were dissolved in dry THF (210 mL) and degassed (vacuum/nitrogen cycles×4). Et3N (107.0 g, 0.1474 L, 1.057 mol) and TMS-acetylene (44.97 g, 0.06471 L, 0.4579 mol) were added and the resultant mixture was stirred at ambient temperature for 1¼ hours. The reaction was cooled in an ice-bath and ether (210 mL) was added. The resultant mixture was stirred at 0° C. for ½ hour, filtered through celite and the celite was washed copiously with ether. The filtrate was concentrated under reduced pressure to give a brown/black solid which was redissolved in the minimum necessary DCM and purified by column chromatography (eluting with DCM). The product containing fractions were concentrated in vacuo and the residue recrystallised from cyclohexane. The precipitate was isolated by filtration to give the sub-title compound as a white powder (80.25 g, 84% Yield). Analytical data identical to that of commercially available compound.

Provenance & Evidence