Toluene → 1-(2-Diethylaminoethyl)-4-bromo-6-[3-(2-oxo-1,3-oxazolin-3-yl)-1-propynyl]-3-hydroxy-3-(2-chlorophenyl)oxindole

Participants

Reaction Conditions

Reaction Steps

To 1-(2-diethylaminoethyl)-3-hydroxy-3-(2-chlorophenyl)-4-bromo-6-iodooxindole (31.5 mg, 5.84×10−5 mol), 3-(2-Oxo-1,3-oxazolin-3-yl)-1-propyne (10.95 mg, 1.5 eq.), Pd(PPh3)2Cl2 (6.15 mg, 15 mol %) and CuI (1.7 mg, 15 mol %) under a nitrogen atmosphere was added anhydrous Et3N (0.5 mL), anhydrous toluene (0.5 mL) and anhydrous THF (0.5 mL). The resulting yellow mixture was heated to 50° C. (bath temperature) and stirred at that temperature for 1 hour and 20 minutes. The solvent was then removed in vacuo to give a yellow solid. Purification was carried out by column chromatography (silica gel, 3% MeOH in CHCl3) to yield the title compound (24.9 mg, 76%) as a white solid. The hydrochloride of the title compound was obtained by treating with 4 N HCl in dioxane followed by concentration to dryness.

Provenance & Evidence