Potassium Phosphate, Tribasic → 5-(3-(4-fluorobenzyl)-4-oxo-3,4-dihydro-2H-pyrido[4,3-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 (134 mg, 0.27 mmol) and 6-bromo-3-(4-fluorobenzyl)-2H-pyrido[4,3-e][1,3]oxazin-4(3H)-one (75 mg, 0.22 mmol) in DMF (2 mL) were added Pd(dppf)Cl2 (18 mg, 0.02 mmol) and K3PO4 (331 mg, 0.66 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[4,3-e][1,3]oxazin-6-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (80 mg, yield: 57%). 1H-NMR (CDCl3, 400 MHz) δ 8.52 (s, 1H), 8.08 (s, 1H), 8.01˜7.97 (m, 3H), 7.69 (s, 1H), 7.35 (dd, J=6.0, 8.4 Hz, 2H), 7.20 (t, J=8.4 Hz, 2H), 7.08 (t, J=8.4 Hz, 2H), 5.91 (s, 1H), 5.23 (s, 2H), 4.77 (s, 2H), 3.27 (s, 3H), 3.01 (d, J=4.8 Hz, 3H), 2.85 (s, 3H). MS (M+H)+: 633.

Provenance & Evidence