1H-Indole-4-boronic acid → (R)-4-(2-(1H-indol-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)cyclohexanol

Participants

Reaction Steps

The title compound was prepared in a manner similar to Example 2 using (R)-4-(2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)cyclohexanol (PREPARATION x63, 30 mg, 0.092 mmol), 1H-indol-4-ylboronic acid (71.9 mg, 0.447 mmol) and PdCl2(dppf) (8.17 mg, 0.011 mmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL) (2 mg, 5%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.32-1.85 (m, 6 H), 2.78-2.93 (m, 1 H), 2.96-3.11 (m, 1 H), 3.50-3.75 (m, 6 H), 3.81-3.90 (m, 2 H), 3.94-4.10 (m, 1 H), 4.36-4.45 (m, 1 H), 4.49-4.60 (m, 1 H), 6.51-6.62 (m, 1 H), 7.02-7.19 (m, 1 H), 7.27-7.45 (m, 3 H), 7.80-7.98 (m, 2 H), 11.04-11.16 (m, 1 H); ESI-MS m/z [M+H]+ calc'd for C23H27N5O2, 406.22; found 406.4.

Provenance & Evidence