Dimethylamine → HCID 46842452, compound

Participants

Reaction Steps

Dimethylamine (0.3 mL, 0.58 mmol) was added to a solution of tert-butyl 5-(3-(4-bromophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)-1H-indole-1-carboxylate (0.200 g, 0.38 mmol), NatOBu (0.112 g, 1.20 mmol), Pd(OAc)2 (0.013 g, 0.06 mmol) and (t-Bu)3PHBF4 (0.034 g, 0.12 mmol) were added to toluene (5 mL). The mixture was microwaved at 300 W (max. power) and 90° C. for 30 min, before the mixture was concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 20% to 60% EtOAc in hexanes, afforded the title compound as a brown-yellow solid (0.048 g, 33%). 1H-NMR (300 MHz, DMSO-d6): δ11.14 (s, 1H), 8.16 (d, J=7.7 Hz, 1H), 7.83-7.88 (m, 1H), 7.67-7.73 (m, 2H), 7.52-7.57 (m, 1H), 7.33 (s, 1H), 7.18 (d, J=8.7 Hz, 1H), 7.03-7.08 (m, 3H), 6.54 (d, J=8.8 Hz, 2H), 6.39 (s, 1H), 2.83 (s, 6H). MS (APCI) m/z: 381 (M+H)+.

Provenance & Evidence