Dimethylformamide → 5-[4-(azetidin-3-yl)phenyl]-6-chloro-1H-indole-3-carbaldehyde

Participants

Reaction Steps

To a solution of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (80 mg, 0.30 mmol) in dioxane (2 mL) was added Vilsmeier salt (150 mg, mmol) and DMF (0.1 mL). The resulting mixture was stirred at room temperature for 20 min. The reaction was quenched with 2 N K2CO3 (1.5 mL, 3.0 mmol). 3-(4-Bromophenyl)azetidine (64 mg, 0.30 mmol) and Pd(dppf)Cl2 (20 mg, 0.030 mmol) were next added, and then heated to 90° C. for 30 min. The reaction mixture was extracted with ethyl acetate (3 mL×3). The combined organic layers were concentrated in vacuo to afford the title compound (94 mg, quantitative yield), which was used directly for the next step without further purification.

Provenance & Evidence