Isatoic Anhydride → 7-Bromo-4-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-pyrido[3,4-b]indole-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(3-amino-2-methylphenyl)-7-bromo-9H-pyrido[3,4-b]indole-1-carboxamide (0.243 g, 0.615 mmol), 1H-benzo[d][1,3]oxazine-2,4-dione (0.251 g, 1.537 mmol), tris(nitrooxy)lanthanum, 6H2O (0.080 g, 0.184 mmol), and trimethoxymethane (2.020 mL, 18.44 mmol) in tetrahydrofuran (2 mL) was heated at 90° C. for 16 hr. The mixture was diluted with ethyl acetate (120 mL), washed with water (2×30 mL) and brine (30 mL), and dried over anhydrous MgSO4. The desired product (0.198 g, 0.378 mmol, 61.4% yield) was isolated as a yellow solid by ISCO (40 g silica gel, solid loading, 40-80% ethyl acetate/hexane).

Provenance & Evidence