Potassium Phosphate, Tribasic → 5-(3-(4-fluorobenzyl)-4-oxo-3,4-dihydro-2H-pyrido[3,2-e][1,3]oxazin-6-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzofuran-3-carboxamide (98 mg, 0.19 mmol) and 6-bromo-3-(4-fluorobenzyl)-2H-pyrido[3,2-e][1,3]oxazin-4(3H)-one (60 mg, 0.18 mmol) in DMF (2 mL) were added Pd(dppf)Cl2 (16 mg, 0.02 mmol) and K3PO4 (270 mg, 0.54 mmol) under N2. After being stirred at 100° C. overnight, the reaction mixture was cooled to RT and filtered. The filtrate was washed with brine and dried over Na2SO4. After being concentrated, the residue was purified by prep-TLC (PE:EtOAc=1:1) to give the product of 5-(3-(4-fluorobenzyl)-4-oxo-3,4-dihydro-2H-pyrido[3,2-e][1,3]oxazin-6-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (80 mg, yield: 70%). 1H-NMR (CDCl3, 400 MHz) δ 8.48 (d, J=2.4 Hz, 1H), 8.44 (d, J=2.4 Hz, 1H), 7.94 (dd, J=5.2, 8.8 Hz, 2H), 7.86 (s, 1H), 7.65 (s, 1H), 7.35 (dd, J=5.2, 8.4 Hz, 2H), 7.22 (t, J=8.8 Hz, 2H), 7.07 (t, J=8.8 Hz, 2H), 5.86 (d, J=4.4 Hz, 1H), 5.31 (s, 2H), 4.75 (s, 2H), 3.21 (s, 3H), 3.00 (d, J=5.2 Hz, 3H), 2.86 (s, 3H). MS (M+H)+: 633.

Provenance & Evidence