Potassium Carbonate → 2-(azetidin-1-yl)-1H-indole

Participants

Reaction Steps

N-tert-Butyloxycarbonyl-3-formylmethylazetidine (0.4 g, 2.01 mmol) was added to a solution of 4-(1,2,4-triazol-1-yl)phenylhydrazine (0.35 g, 2.01 mmol) in 4% H2SO4 (50 ml) and the mixture refiuxed for 16h. The mixture was then cooled to room temperature, basified (K2CO3) and extracted with n-butanol (5 x). The crude product obtained was chromatographed on silica-gel eluting with CH2Cl2 /MeOH/NH3 (20:8:1) to give the title-azetidinylindole (0.186 g, 39%); δ (360 MHz, CD3OD) 3.80-3.88 (4H, m, 2 of CH2 of azetidine), 4.12-4.23 (1H, m, CH), 7.23 (1H, s, Ar--H), 7.39 (2H, s, Ar--H), 7.65 (1H, d, J=2.5 Hz, Ar--H), 8.04 (1H, s, Ar--H), 8.89 (1H, s, Ar--H).

Provenance & Evidence