Sodium Bicarbonate → HCID 23365858, compound

Participants

Reaction Steps

A slurry of methyl 4-[1-(3-methylbut-2-enyl)-5-nitroindol-3-ylmethyl]-3-methoxybenzoate (0.22 g.) and stannous chloride dihydrate (1.6 g.) in absolute ethanol (8 ml.) was heated and stirred under reflux under an atmosphere of nitrogen for 24 hours. The cooled mixture was poured into saturated sodium bicarbonate solution (30 ml.). The mixture obtained was extracted with dichloromethane (2×30 ml.). The combined extracts were washed with saturated brine (25 ml.), dried and evaporated to give methyl 4-[5-amino-1-(3-methylbut-2-enyl)indol-3-ylmethyl]-3-methoxybenzoate (F) (0.14 g.; 69%) an oil; NMR: 1.68(s,3H, =C--CH3), 1.76(s,3H, =C--CH3), 3.82(s,3H, CO.OCH3), 3.89 (s,2H, CH2.Ar), 3.91(s,3H, OCH3), 4.57(d,2H, CH2N), 5.27(t,1H, CH2CH), 6.48(m,2H), 6.91 (s,1H), 7.04(d,1H), 7.08(d,1H), 7.46(m,2H).

Provenance & Evidence