Water → HCID 89650816, compound

Temperature

100 °C

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.

1. temperaturecooled to room temperature
2. additionThe mixture was poured onto water (50 mL)
3. customthe layers separated
4. extractionThe aqueous phase was further extracted with EtOAc (2×50 mL)
5. washThe combined organic phase was washed with brine (50 mL)
6. dry with materialdried (MgSO4)
7. customto give the crude product as a brown solid
8. washColumn chromatography (SiO2), eluting with 1% MeOH in DCM

ORD record

ord-755484633d124ac7be9977d563d0648d

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09060515B2