Potassium Carbonate → 6-Chloro-5-(4-(1-(hydroxymethyl)cyclopropyl)phenyl)-1h-indole-3-carbaldehyde

Participants

Reaction Steps

A mixture of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (156 mg, 0.60 mmol) and N,N-dimethylformiminium chloride (150 mg, 1.20 mmol) in dry 1,4-dioxane (4 mL) and DMF (0.7 mL) was sealed in a vial and stirred at room temperature for 10 min to give a white slurry. To the reaction mixture was then added 2M aqueous potassium carbonate (2.5 mL, 5 mmol), [1-(4-bromophenyl)cyclopropyl]methanol (140 mg, 0.6 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg). The reaction mixture was degassed and heated to 90° C. for 30 min. The cooled reaction mixture was diluted with water (20 mL), and then washed with EtOAc (3×20 mL). The combined organic layers were dried and concentrated in vacuo to give crude 6-chloro-5-{4-[1-(hydroxymethyl)cyclopropyl]phenyl}-1H-indole-3-carbaldehyde (160 mg, 90% yield), which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 11.10 (s, 1H), 8.77 (s, 1H), 8.56 (s, 1H), 7.92 (s, 1H), 7.39-7.34 (m, 4H), 4.70 (br.s., 1H), 3.56 (s, 2H), 0.88-0.86 (m, 2H), 0.79-0.77 (m, 2H).

Provenance & Evidence