1-Bromo-3-methylbutane → 5-Amino-3,3-dimethyl-1-(3-methyl-butyl)-6-nitro-1,3-dihydro-indol-2-one

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Reaction Steps

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (1 g) is alkylated using 1-bromo-3-methylbutane (1.9 ml; 15.4 mmol) and K2CO3 (2.1 g; 15.2 mmol) at RT for 24 h. After aqueous work-up and flash chromatography the pure material (0.62 g; 1.86 mmol) is de-acetylated under reflux in 2-propanol (2 ml) and hydrochloric acid (6 N; 7 ml). Pure 5-amino-3,3-dimethyl-1-(3-methyl-butyl)-6-nitro-1,3-dihydro-indol-2-one (419 mg) is obtained by flash chromatography on silica gel eluting with CH2Cl2/MeOH (50:1).

Provenance & Evidence