4-Vinylpyridine → HCID 178424552, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-((3,4-dichlorophenyl)amino)-8-bromo-6-methyl-5-nitroquinazolin-4-ol (65 mg) in N,N-dimethylformamide (2 mL) was added 4-vinylpyridine (0.040 mL), followed by palladium acetate (14 mg), tri-o-tolylphosphine (30 mg) and N,N-diisopropylethylamine (0.44 mL). The mixture was heated at 120° C. for 22.5 h, then was cooled to room temperature. The supernatant was concentrated in vacuo to a dark oil which was triturated with a 50% (v/v) methanol/dichloromethane (5 mL). The solid product was isolated by filtration, washed with 50% (v/v) methanol/dichloromethane (5 mL) and dried to give the title compound (12 mg). 1H NMR (300 MHz, DMSO-d6) δ11.55 (s, 1H), 9.23, 8.59 (d, J=4.5 Hz, 2H), 8.43 (d, J=2.4 Hz, 1H), 8.21 (s, 1H), 8.08 (d, J=16.8 Hz, 1H), 7.62-7.31 (m, 5H), 2.26 (s, 3H). HPLC (Method B) 9.3 min. MS (APCI+): m/z 468.

Provenance & Evidence