2-amino-5-bromo-N-phenylbenzamide

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-amino-5-bromo-N-phenylbenzamide (2.82 g, 9.7 mmol) and triethyl orthoformate (20 mL) was stirred at 130° C. for 15 h. The reaction mixture was cooled to RT and petroleum ether was added. After filtration, the filtrate was extracted with ethyl acetate (100 mL*3), the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with silica gel column chromatograph (PE:EtOAc=5:1) to give 6-bromo-3-phenylquinazolin-4(3H)-one (1.5 g, yield: 50%) as white solid. 1H-NMR (CDCl3, 400 MHz) δ 8.50 (d, J=2.4 Hz, 1H), 8.13 (s, 1H), 7.87˜7.90 (m, 1H), 7.65 (d, J=8.8 Hz, 1H), 7.55˜7.58 (m, 2H), 7.51˜7.53 (m, 1H), 7.41˜7.43 (m, 2H). MS (M+H)+:301/303. The reaction mixture was cooled to RT After filtration the filtrate was extracted with ethyl acetate (100 mL*3) the combined organic layers were washed with brine dried over anhydrous sodium sulfate filtered concentrated The residue was purified with silica gel column chromatograph (PE:EtOAc=5:1)

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-amino-5-bromo-benzoic acid (2 g, 9.26 mmol) and SOCl2 (4 mL) in toluene (20 mL) was stirred at 130° C. for 2 h. After being concentrated, the residue was dissolved in tetrahydrofuran (50 mL) and phenylamine was added dropwise at 0° C. Then the reaction mixture was heated to 90° C. for 4 h. The mixture was cooled to room temperature, quenched with saturated aqueous K2CO3 (20 mL) and extracted with ethyl acetate (50 mL*3), the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with silica gel column chromatograph (PE:EtOAc=4:1) to give 2-amino-5-bromo-N-phenylbenzamide (2.82 g, yield: 99%) as white solid. MS (M+H)+: 291/293. After being concentrated the residue was dissolved in tetrahydrofuran (50 mL) phenylamine was added dropwise at 0° C Then the reaction mixture was heated to 90° C. for 4 h The mixture was cooled to room temperature quenched with saturated aqueous K2CO3 (20 mL) extracted with ethyl acetate (50 mL*3) the combined organic layers were washed with brine dried over anhydrous sodium sulfate filtered concentrated The residue was purified with silica gel column chromatograph (PE:EtOAc=4:1)