4-Bromotoluene → HCID 86698688, compound

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), 4-bromotoluene (56 mg, 0.30 mmol), 2.0M aqueous potassium carbonate (0.5 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 to give a residue, which was purified by preparative TLC to give the title compound (80 mg, 100% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.51 (br. s, 1H), 8.15 (s, 1H), 7.98 (s, 1H), 7.55 (s, 1H), 7.42 (d, 2H), 7.25 (d, 2H), 3.90 (s, 3H), 2.42 (s, 3H).

Provenance & Evidence