3,7-DIMETHYL-1H-INDOLE-2-CARBALDEHYDE synthesis

Yield:1463-72-5 46%

Reaction Conditions:

with manganese(IV) oxide in dichloromethane at 20;

Steps:

80.c

c) 3,7-Dimethyl- lH-indole-2-carbaldehyde:; A mixture of (3,7-dimethyl-lH-indol-2-yl)methanol (440 mg, 2.5 mmol) and manganese dioxide (1.09 g, 12.5 mmol) in dichloromethane (15 mL) was stirred overnight at rt. The mixture was filtered and evaporated. The crude was chromatographed over silica gel eluting with ethyl acetate / hexane (5% and 7.5%) to afford the title compound (200 mg, 46%). ¹HNMR (400 MHz, CDCl₃) δ 10.00 (s, IH), 8.75 (s, IH), 7.51 (d, J= 7.2 Hz, IH), 7.15 (d, J= 7.4 Hz, IH), 7.05 (t, J= 7.3 Hz, IH), 2.61 (s, 3H), 2.45 (s, 3H).

References:

WO2007/53131,2007,A2 Location in patent:Page/Page column 187