m-Chlorostyrene → HCID 178424511, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-((3,4-dichlorophenyl)amino)-8-bromo-6-methylquinazolin-4-ol (29 mg) in DMF (2 mL) was added 3-chlorostyrene (0.020 mL), followed by palladium acetate (4.0 mg), tri-o-tolylphosphine (9.0 mg) and N,N-diisopropylethylamine (0.20 mL). The resulting mixture was heated at 120° C. for 24 h, then was cooled to room temperature. The supernatant was concentrated in vacuo to a dark semi-solid which was triturated with 50% (v/v) methanol/dichloromethane (4 mL) and diethyl ether (ca. 0.1 mL) to afford the title compound as a tan solid (20 mg). 1H NMR (300 MHz, DMSO-d6): δ11.0 (s, 1H), 9.06 (s, 1H), 8.55 (d, J=2.6 Hz, 1H), 7.99 (d, J=2.0 Hz, 1H), 7.98 (d, J=16.7 Hz, 1H), 7.78 (d, J=2.0 Hz, 1H), 7.69 (dd, J=1,8, 1.8 Hz, 1H), 7.59 (d, J=8.6 Hz, 1H), 7.59 (dd, J=8.0, 1.8 Hz, 1H), 7.43 (dd, J=8.9, 8.0 Hz, 1H), 7.39 (dd, J=8.6, 2.6 Hz, 1H), 7.37 (d, J=16.7 Hz, 1H), 7.35 (m, 1H), 2.43 (s, 3H). HPLC (Method B) 11.7 min. MS (APCI+): m/z 456, 458.

Provenance & Evidence