1-Ethenyl-4-methylbenzene → HCID 178424838, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-((3,4-dichlorophenyl)amino)-6-fluoro-8-iodoquinazolin-4-ol (45 mg) and palladium acetate (13.5 mg) in dimethylformamide (1.3 mL) was added 4-methylstyrene (26 μL), diisopropylethylamine (200 μL) and tri-o-tolylphosphine (12 mg). The resulting mixture was heated at 120° C. for 3 h. The mixture was then cooled to room temperature and the supernatant was removed by pipette from the settled black solids. The solvent and the excess volatile reagents were removed in vacuo, providing the crude product as a brown solid. This residue was triturated with 50% (v/v) methanol/dichloromethane (3 mL) and the resulting yellow solid was dried in vacuo to afford the title compound (25.1 mg). 1H NMR (300 MHz, DMSO-d6): δ11.24 (brs, 1H), 9.12 (brs, 1H), 8.59 (d, J=2.4 Hz, 1H), 8.04 (dd, J=3 & 10.2 Hz, 1H), 7.91 (d, J=16.8 Hz, 1H), 7.62-7.56 (m, 4H), 7.47 (d, J=16.8 Hz, 1H), 7.36 (dd, J=2.4 & 9 Hz, 1H), 7.31 (d, J=6 Hz, 2H), 2.34 (s, 3H). MS (APCI+): m/z 440.

Provenance & Evidence