Sodium Carbonate → 5-(11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)-2-morpholinobenzofuran-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of N-methyl-6-(N-methylmethylsulfonamido)-2-morpholino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (80 mg, 0.16 mmol), 2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (47 mg, 0.17 mmol), Na2CO3 (34 mg, 0.32 mmol) in dioxane (1.5 mL) and H2O (0.1 mL) was added Pd(dppf)Cl2 (3 mg) under N2. Then the mixture was stirred at 100° C. for 2 hours. The reaction mixture was cooled to RT and filtered. The filtrate was washed with H2O and dried over Na2SO4. After concentration, the residue was purified by prep-HPLC to give the product of 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)-2-morpholinobenzofuran-3-carboxamide (10 mg, yield: 10%). 1H-NMR (CDCl3, 400 MHz) δ 8.01 (s, 1H), 7.45˜7.47 (m, 3H), 7.18˜7.21 (m, 2H), 7.12 (d, J=8.0 Hz, 1H), 6.82˜6.87 (m, 1H), 6.64 (s, 1H), 5.99 (s, 2H), 3.89 (t, J=4.4 Hz, 4H), 3.51 (t, J=6.4 Hz, 4H), 3.36 (s, 3H), 3.01 (d, J=4.8 Hz, 3H), 2.68 (s, 3H). MS (M+H)+: 606.

Provenance & Evidence