Cesium carbonate → HCID 117772681, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-N-((5-fluoropyridin-2-yl)methyl)-3-hydroxypicolinamide (30 mg, 0.05 mmol) and Cs2CO3 (47 mg, 0.14 mmol) in DMF (3 mL) at 100° C. was added chloroiodomethane (13 mg, 0.07 mmol) under N2 protection dropwise. The mixture was stirred at 100° C. for 3 h. The mixture was concentrated, diluted with water and extracted with EtOAc. The organic phase was dried over Na2SO4 After concentration, the residue was purified by prep-HPLC to give the product of 2-(4-fluorophenyl)-5-(3-((5-fluoropyridin-2-yl)methyl)-4-oxo-3,4-dihydro-2H-pyrido[2,3-e][1,3]oxazin-6-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (20 mg, yield: 60%). 1H-NMR (CDCl3, 400 MHz) δ 8.33 (s, 1H), 7.90˜7.94 (m, 3H), 7.69 (d, J=8.8 Hz, 1H), 7.56 (s, 1H), 7.40˜7.44 (m, 2H), 7.31˜7.36 (m, 1H), 7.13 (t, J=8.8 Hz, 2H), 6.19 (br s, 1H), 5.43 (s, 2H), 4.82 (s, 2H), 3.15 (s, 3H), 2.92 (d, J=4.8 Hz, 3H), 2.85 (s, 3H). MS (M+H)+: 634.

Provenance & Evidence