1H-Indole-4-boronic acid → HCID 60197266, compound

Participants

Reaction Conditions

Reaction Steps

To a 10 mL vial were added 2-((2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)methyl)-4-methylbenzamide (PREPARATION x84, 57 mg, 0.152 mmol), 1H-indol-4-ylboronic acid (49.1 mg, 0.305 mmol), and PdCl2(dppf) (11.16 mg, 0.015 mmol) in dioxane (2 mL) and saturated NaHCO3 (0.4 mL). The resulting orange suspension was heated to 100° C. and stirred overnight. The reaction mixture was subsequently diluted with EtOAc and washed with saturated NH4Cl (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated. The product was purified by preparative HPLC, using a 20-45% CH3CN gradient in H2O (with 0.05% TFA). The pure fractions were combined and lyophilized to give the title compound as a yellow solid (23 mg, 33%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.33 (s, 3 H), 3.06-3.19 (m, 1 H), 3.24-3.33 (m, 2 H), 3.56-3.64 (m, 1 H), 3.89-4.05 (m, 1 H), 4.06-4.18 (m, 1 H), 4.41-4.55 (m, 1 H), 4.67-4.81 (m, 2 H), 6.94-7.08 (m, 1 H), 7.21-7.33 (m, 2 H), 7.33-7.41 (m, 1 H), 7.44-7.54 (m, 1 H), 7.54-7.74 (m, 2 H), 7.79-7.91 (m, 1 H), 11.46-11.66 (m, 1H); ESI-MS m/z [M+H]′ calc'd for C26H26N6O2, 455.2; found 455.3.

Provenance & Evidence