Water → HCID 59290460, compound

Participants

Reaction Conditions

Reaction Steps

Pd-118 (104 mg) was dissolved in acetonitrile (10 mL) and stirred for 5 min before addition of potassium carbonate (2.364 g), water (10 mL) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.305 g). The mixture was stirred for a further 5 min then tert-butyl 3-(3-bromo-2-fluorophenethoxy)propanoate [Example 16, Step iii)] (1.98 g) added and the reaction was heated at the heating block (80° C.) for 2 h. The mixture was cooled and extracted into ethyl acetate (150 mL). Organic was separated, dried (MgSO4) solvents evaporated to give a brown oil. The crude product was purified by flash silica chromatography, elution gradient 0 to 60% ethyl acetate in isohexane to afford the subtitled compound (1.480 g) as a gum. MS [M+H-C4H9]+=293 (MultiMode+) 1H NMR (300 MHz, CDCl3) δ 7.83 (s, 1H), 7.75 (d, J=2.5 Hz, 1H), 7.39 (td, J=2.5 and 7.3 Hz, 1H), 7.13-7.01 (m, 2H), 3.96 (s, 3H), 3.74-3.64 (m, 4H), 2.96 (t, J=6.8 Hz, 2H), 2.49 (t, J=6.4 Hz, 2H), 1.44 (s, 9H).

Provenance & Evidence