1-(Trimethylsilyl)prop-1-yne → HCID 57856278, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-3-iodopyridin-2-amine (B-5-2) (30 g, 0.1 mol) in DMF (600 mL) were added KOAc (29.4 g, 0.3 mol) and LiCl (4.25 g, 0.1 mol). After the mixture was degassed under N2 for 3 times, Pd(OAc)2 (2.24 g, 0.01 mol) was added, and the mixture was degassed again. Then trimethyl-prop-1-ynyl-silane (56 g, 0.5 mol) was added. The resulting mixture was heated to 80-100° C. for 2 days. TLC (EtOAc: Petroleum ether=1:5) showed that the reaction was complete. Excess DMF was removed under reduced pressure. The residue was dissolved in EtOAc (500 mL), washed with saturated aqueous NaCl, dried over Na2SO4 and concentrated to give crude product, which was purified via a silica gel column chromatography (100-200) (Petroleum ether, then EtOAc:Petroleum ether=1:10) to give 5-bromo-3-methyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine (B-5-3) (not pure, 5 g, 17.7%) as a brown oil.

Provenance & Evidence