Potassium Carbonate → 6-chloro-5-[4-(oxetan-3-ylmethoxy)phenyl]-1H-indole-3-carbaldehyde

Participants

Reaction Steps

To a sealed tube was added 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (100 mg, 0.38 mmol) and N,N-dimethylformiminium chloride (97.7 mg, 0.76 mmol) in dioxane/DMF=5/1 (6 mL). The sealed vial was stirred at room temperature for 10 min. to give a white slurry. To the slurry was added 2M potassium carbonate (1.0 mL, 1.9 mmol), 3-[(4-bromophenoxy)methyl]oxetane (92.3 mg, 0.38 mmol) and Pd(dppf)Cl2 (30 mg, 0.05 mmol). The sealed vial was heated to 90° C. for 30 min. TLC (petroleum ether/ethyl acetate=1:1) showed the reaction was complete. The reaction was quenched with water (20 mL), then washed with EtOAc (20 mL×3). The combined organics was dried over sodium sulfate, filtered, concentrated, and purified by combi-flash to give the title compound (70 mg, 53% yield) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 9.90 (s, 1H), 8.17 (s, 1H), 8.11 (s, 1H), 7.62 (s, 1H), 7.38 (d, 2H) 7.03 (d, 2H), 4.92 (m, 2H), 4.65 (t, 1H), 4.61 (s, 1H), 4.28-4.27 (m, 2H), 3.50 (m, 1H).

Provenance & Evidence