2-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indole → HCID 90341055, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of compound methyl 3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-2-carboxylate (700 mg, 1.50 mmol), 2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (536 mg, 1.95 mmol) and K3PO4.3H2O (1.20 g, 4.50 mmol) in 1,4-dioxane (25 mL), Pd2(dba)3/XPhos (50 mg/50 mg) was added under N2 protection. After stirring at 100° C. for 3 h, the reaction mixture was concentrated in vacuo, suspended in water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by prep-TLC (DCM:MeOH=200:1) to give the product of methyl 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carboxylate (700 mg, yield: 80%). 1H-NMR (CDCl3, 400 MHz) δ 9.41 (br s, 1H), 8.79 (s, 1H), 7.74 (s, 1H), 7.55˜7.45 (m, 2H), 7.24˜7.17 (m, 2H), 7.12 (d, J=8.0 Hz, 1H), 6.88˜6.81 (m, 1H), 6.01 (s, 2H), 4.10 (s, 3H), 3.40 (s, 3H), 3.05 (d, J=4.4 Hz, 3H), 2.69 (s, 3H). MS (M+H)+: 579.

Provenance & Evidence