Methanol → HCID 87055890, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-3-(4-chlorobenzyl)-2H-pyrido[2,3-e][1,3]oxazin-4(3H)-one (127 mg, 0.36 mmol), 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (150 mg, 0.30 mmol) and K3PO4.3H2O (159 mg, 0.60 mmol) in dioxane/water (2 mL/0.2 mL) was added Pd(dppf)Cl2 (10 mg) under nitrogen. The mixture was heated at 100° C. for 5 h, and after concentrated in vacuo, the residue was suspended in water. The mixture was extracted with EtOAc and the organic phase was washed with brine then dried over sodium sulfate. The product 5-(3-(4-chlorobenzyl)-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 (140 mg, yield: 72%) was obtained with prep-TLC (DCM:MeOH=30:1). 1H-NMR (CDCl3, 400 MHz) δ 7.95˜7.98 (m, 3H), 7.76 (d, J=8.8 Hz, 1H), 7.63 (s, 1H), 7.45 (d, J=8.4 Hz, 1H), 7.30˜7.36 (m, 4H), 7.20 (t, J=8.8 Hz, 2H), 6.07 (br s, 1H), 5.23 (s, 2H), 4.79 (s, 2H), 3.23 (s, 3H), 2.99 (d, J=4.8 Hz, 3H), 2.94 (s, 3H). MS (M+H)+: 649/651.

Provenance & Evidence