Dimethylamine → HCID 59441803, compound

Participants

Reaction Steps

To a solution of 6-(methyloxy)-5-nitro-2,3-dihydro-1H-indole (1.1 g, 5.67 mmol) and potassium carbonate (2.34 g, 17.17 mmol) in THF (250 mL) was added bromoacetyl chloride (0.98 g, 6.23 mmols) via a dropwise addition. After stirring 2 hrs at rt, catalytic Kl was added followed by a 2.0M solution of dimethylamine in tetrahydrofuran (17 mL). After overnight stirring, the reaction was diluted with ethyl acetate and washed with water (200 mL). The organic layer was adsorbed onto silica gel and purified by column chromatography (DCM to 10% MeOH/DCM) to afford N,N-dimethyl-2-[6-(methyloxy)-5-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethanamine (0.55 g, 35% over two steps). ESIMS (M+H)+=280.

Provenance & Evidence