Potassium Carbonate → Indole

Participants

Reaction Steps

N-tert-Butyloxycarbonyl-3-formylmethylazetidine (0.3 g, 1.51 mmol) was added to a solution of 4-(2-methylimidazol-1-ylmethyl)phenylhydrazine (0.36 g, 1.51 mmol) in 4% H2SO4 (25 ml) and the resulting solution refluxed for 3h. The mixture was then cooled to room temperature, basified with K2CO3 and extracted with n-butanol (2×100 ml). The combined extracts were dried (MgSO4), evaporated, and the residue chromatographed through silica-gel eluting with CH2Cl2 /MeOH/NH3 (20:8:1) to give the title-indole (0.186 g, 46%), mp 88°-90° C.; δ (250 MHz, CD3OD) 2.02 (3H, s, CH3), 3.76-3.86 (4H, m, 2 of CH2), 4.04-4.20 (1H, m, CH of azetidine), 5.06 (2H, s, CH2), 6.70 (1H, d, J=1.4 Hz, Ar--H), 6.82 (1H, dd, J=1.5 and 8.4 Hz, Ar--H), 6.90 (1H, d, J=1.4 Hz, Ar--H), 7.12 (1H, s, Ar--H), 7.23 (1H, d, J =8.4Hz, At-H), 7.26 (1H, d, J =1.5Hz, Ar--H).

Provenance & Evidence