Lithium Chloride → 5-(11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-N-methyl-2-(5-methyl-1,3,4-oxadiazol-2-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of compound 5-bromo-N-methyl-2-(5-methyl-1,3,4-oxadiazol-2-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (70 mg, 0.16 mmol), 11-fluoro-2-(trimethylstannyl)-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (95 mg, 0.24 mmol) and LiCl (20 mg, 0.47 mmol) in IPA (2 mL), chloro[(tricyclohexylphosphine)-2-(2′-aminobiphenyl)]palladium(II) (50 mg) was added under N2 protection. After stirring at 100° C. overnight, the reaction mixture was concentrated in vacuo. The residue was purified by prep-TLC (DCM:MeOH=100:1) 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-2-(5-methyl-1,3,4-oxadiazol-2-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (20 mg, yield: 21%). 1H-NMR (CDCl3, 400 MHz) δ 9.81 (br s, 1H), 8.81 (s, 1H), 7.77 (s, 1H), 7.55˜7.46 (m, 2H), 7.25˜7.18 (m, 2H), 7.13 (s, 1H), 6.89˜6.80 (m, 1H), 6.01 (s, 2H), 3.41 (s, 3H), 3.09 (d, J=4.4 Hz, 3H), 2.76 (s, 3H), 2.68 (s, 3H). MS (M+H)+: 603.

Provenance & Evidence