Ethyl Acetate → methyl 6-chloro-5-{4-[2-(piperazin-1-yl)ethoxy]phenyl}-1H-indole-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (80 mg, 0.15 mmol), 1-(2-(4-bromophenoxy)ethyl)piperazine (86 mg, 0.30 mmol), 2.0M aqueous potassium carbonate (0.50 mL, 1.0 mmol), and Pd(dppf)Cl2 (10 mg, 0.01 mmol) in toluene/ethanol (1.44 mL/0.48 mL) was stirred at 110° C. for 2.5 hours. The mixture was poured into ethyl acetate and washed with water. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo to give a residue, which was purified by preparative TLC to give the title compound (40 mg, 40% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ8.50 (s, 1H), 8.10 (s, 1H), 7.98 (s, 1H), 7.55 (m, 1H), 7.45 (m, 2H), 7.00 (m, 2H), 4.20 (m, 2H), 3.90 (s, 3H), 2.99 (m, 4H), 2.85 (m, 2H), 2.60 (m, 4H).

Provenance & Evidence