Dimethylamine → HCID 59442138, compound

Participants

Reaction Steps

A slurry of (2S)-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole hydrogen chloride (4.43 g, 18.11 mmol) and K2CO3 (10.01 g, 72.4 mmol) in THF (200 mL) at 0° C. was treated with bromoacetyl chloride (3.02 mL, 36.2 mmol). After 2 h the resulting mixture was allowed to warm to rt. A 2M Me2NH solution in THF (54.3 mL, 109 mmol) was added. After 18 h the resulting thick slurry was filtered and the solids were washed with EtOAc. The filtrate was concentrated onto Celite and purified by silica gel chromatography using 1-10% MeOH (containing 0.2% NH3)/CH2Cl2. The foamy oily product was chased using CH2Cl2 and hexanes, CH2Cl2 and Et2O, then Et2O to obtain N,N-dimethyl-2-[(2S)-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethanamine as an orange solid (2.50 g, 47%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (d, J=6.04 Hz, 3H), 2.28 (s, 6H), 2.75 (d, J=17.21 Hz, 1H), 3.14 (d, J=14.65 Hz, 1H), 3.44 (d, J=14.65 Hz, 2H), 3.90 (s, 3H), 4.75-4.92 (m, 1H), 7.37 (s, 1H), 8.43 (s, 1H); ESIMS (M+H)+=293.88.

Provenance & Evidence