Toluene → 1-(2-Diethylaminoethyl)-3-hydroxy-3-(2-chlorophenyl)-4-bromo-6-[3-(N-ethylureido)-1-propynyl]oxindole

Participants

Reaction Conditions

Reaction Steps

To 1-(2-diethylaminoethyl)-3-hydroxy-3-(2-chlorophenyl)-4-bromo-6-iodooxindole (21.0 mg, 3.89×10−5 mol), N-ethyl-N′-propargylurea (7.36 mg, 1.5 eq.), Pd(PPh3)2Cl2 (4.10 mg, 15 mol %) and CuI (1.10 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 2 hours. The solvent was then removed in vacuo to give a yellow solid. Purification was carried out by column chromatography (silica gel, 10% MeOH in CHCl3) to yield the title compound (18.8 mg, 86%) as a light brown solid.

Provenance & Evidence