Sodium Carbonate → HCID 68195353, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-tert-butyl 2-(2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)acetate (PREPARATION x80, 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 1 hour 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 via flash column chromatography (silica-NH, gradient 10-80% EtOAc/hexane) to afford the title compound as an off-white solid (112 mg, 91%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38-1.48 (m, 9 H), 2.98-3.09 (m, 1 H), 3.15-3.40 (m, 3 H), 3.52-3.64 (m, 2 H), 3.87-4.11 (m, 3 H), 4.28 (d, J=17.94 Hz, 1 H), 4.52-4.60 (m, 1 H), 7.12 (t, J=7.71 Hz, 1 H), 7.29-7.44 (m, 3 H), 7.51-7.68 (m, 1 H), 7.93 (dd, J=7.45, 0.88 Hz, 1 H), 11.12 (br s, 1 H); ESI-MS m/z [M+H]+ calc'd for C23H27N5O3, 422.22; found 422.3.

Provenance & Evidence