Sodium Carbonate → (R)-tert-butyl 2-(2-(1H-indol-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-tert-butyl 2-(2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)acetate (PREPARATION x24, 100 mg, 0.293 mmol), indole-4-boronic acid (70.8 mg, 0.440 mmol), tetrakis(triphenylphosphine)palladium(0) (33.9 mg, 0.029 mmol) and sodium carbonate (62.2 mg, 0.587 mmol) in 1,4-dioxane (1 mL) and water (0.5 mL) was heated to 120° C. for 30 minutes in a microwave. After cooling to room temperature, the reaction mixture was diluted with EtOAc, filtered through Celite, washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, 20-80% EtOAc/hexane gradient) to afford the title compound as an off-white solid (110 mg, 89%). 1H NMR (400 MHz, CDCl3) δ 1.48 (s, 9 H), 3.07-3.36 (m, 3 H), 3.42-3.51 (m, 1 H), 3.62-3.79 (m, 3 H), 3.93 (dd, J=10.86, 3.28 Hz, 1 H), 4.01-4.16 (m, 2 H), 4.77 (dd, J=13.39, 2.02 Hz, 1 H), 7.22-7.31 (m, 2 H), 7.39-7.46 (m, 2 H), 7.66 (s, 1 H), 8.01 (dd, J=7.45, 0.88 Hz, 1 H), 8.26 (br s, 1H). ESI-MS m/z [M+H]+ calc'd for C23H27N5O3, 422.21; found 422.3.

Provenance & Evidence