Cesium carbonate → HCID 86765077, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-benzyl-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-3-hydroxypicolinamide (100 mg, 0.17 mmol) and Cs2CO3 (117 mg, 0.33 mmol) in DMF (20 mL) was added chloroiodomethane (47 mg, 0.25 mmol) dropwise at 110° C. under N2. The mixture was stirred at 110° C. for 0.5 hour. Then the mixture was concentrated and extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by prep-TLC (DCM:CH3OH=20:1) to afford the product of 5-(3-benzyl-4-oxo-3,4-dihydro-2H-pyrido[2,3-e][1,3]oxazin-6-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (20 mg, yield: 19.6%). 1H-NMR (CDCl3, 400 MHz) δ 7.88˜7.90 (m, 3H), 7.72˜7.74 (m, 1H), 7.55 (s, 1H), 7.34˜7.39 (m, 5H), 7.25˜7.28 (m, 1H), 7.14 (t, J=7.2 Hz, 2H), 6.87 (br s, 1H), 5.19 (s, 2H), 4.76 (s, 2H), 3.14 (s, 3H), 2.93˜2.94 (m, 6H). MS (M+H)+: 615.

Provenance & Evidence