Ethyl Acetate → methyl 6-chloro-5-{4-[1-(methylsulfonyl)azetidin-2-yl]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 (100 mg, 0.311 mmol), 2-(4-bromophenyl)-1-(methylsulfonyl)azetidine (108.2 mg, 0.373 mmol), 2.0 M potassium carbonate solution (0.5 mL, 1.0 mmol), and Pd(dppf)Cl2 (30 mg, 0.03 mmol) in toluene/ethanol (1.44 mL/0.48 mL) was stirred at 110° C. for 2.5 hours. TLC (petroleum ether/ethyl acetate=3:1) showed that the reaction was complete. The mixture was poured into ethyl acetate and washed with water. The organic phase was dried over sodium sulfate, filtered, and concentrated to give a residue, which was purified by prep-TLC to give the title compound (80 mg, 62% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.30-12.10 (s, 1 H), 8.2 (s, 1 H), 7.92 (s, 1 H), 7.65 (s, 1 H), 7.55 (d, 2 H), 7.45 (d, 2 H), 5.35 (m, 1 H), 4.32 (m, 1 H), 4.0 (m, 1 H), 3.75 (s, 3 H), 3.15 (m, 2 H), 3.05 (s, 3 H).

Provenance & Evidence