Water → HCID 89650816, compound

Participants

Reaction Conditions

Reaction Steps

Palladium (II) acetate (0.240 g, 1.06 mmol) was added to a solution of Xantphos (0.88 g, 1.52 mmol) in degassed 1,4-dioxane (40 mL) at room temperature. The mixture was stirred under N2(g) for 1 h and treated with iii (0.98 g, 3.54 mmol), N-ethylurea (0.470 g, 5.31 mmol), potassium tert-butoxide (0.600 g, 5.31 mmol) and degassed water (96 μL, 5.31 mmol). The mixture was warmed to 100° C. for 2 h, cooled to room temperature and diluted with EtOAc (50 mL). The mixture was poured onto water (50 mL), and the layers separated. The aqueous phase was further extracted with EtOAc (2×50 mL). The combined organic phase was washed with brine (50 mL), dried (MgSO4) and reduced in vacuo to give the crude product as a brown solid. Column chromatography (SiO2), eluting with 1% MeOH in DCM, afforded compound iv (0.501 g, 1.52 mmol, 43%) as an orange solid. 1H NMR (300 MHz, DMSO-d6): δ 10.14 (1H, br s), 9.94 (1H, br s), 8.77-8.74 (2H, m), 7.64 (2H, d, J 7.7), 7.43 (2H, t, J 8.2), 7.20 (1H, t, J 7.7), 4.35 (2H, q, J 7.2), 3.03 (2H, dq, J 5.6 and 7.2), 1.34 (3H, t, J 7.2), 0.88 (3H, t, J 7.2); [M+H]+ m/z=330.1.

Provenance & Evidence