Dimethylamine → HCID 59441760, compound

Participants

Reaction Steps

A 0° C. slurry of (2R)-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole hydrogen chloride (4.55 g, 18.60 mmol) and K2CO3 (10.28 g, 74.4 mmol) in THF (200 mL) was treated with bromoacetyl chloride (3.10 mL, 37.2 mmol). After 2 h the reaction mixture was allowed to warm to rt. A 2M Me2NH solution in THF (55.8 mL, 112 mmol) was added and the reaction mixture was stirred at rt for 18 h. The resulting thick slurry was filtered and the solids were rinsed with EtOAc. The filtrate was concentrated onto Celite and purified by silica gel chromatography using 1-10% MeOH (containing 0.2% NH3)/CH2Cl2 to obtain N,N-dimethyl-2-[(2R)-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethanamine as an orange solid (2.92 g, 54%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (d, J=6.04 Hz, 3H), 2.28 (s, 6H), 2.75 (d, J=17.03 Hz, 1H), 3.14 (d, J=14.83 Hz, 1H), 3.44 (d, J=14.65 Hz, 2H), 3.90 (s, 3H), 4.77-4.92 (m, 1H), 7.36 (s, 1H), 8.43 (s, 1H); ESIMS (M+H)+=294.01.

Provenance & Evidence