Water → tert-Butyl 3-(3-(1-propyl-1H-pyrazol-4-yl)phenethoxy)propanoate

Participants

Reaction Conditions

Reaction Steps

Pd-118 (51.7 mg) was dissolved in acetonitrile (8 mL) and stirred for 5 min before addition of potassium carbonate (1.1 g), water (8 mL) and a solution of 1-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (750 mg) in MeCN (1 mL). The mixture was stirred for a further 5 min then a solution of tert-butyl 3-(3-bromophenethoxy)propanoate (870 mg, prepared as in Preparation 3, Step i)) was added and the reaction was heated at the heating block (80° C.) for 30 min. The mixture was cooled and extracted into DCM. Organic was separated using a phase separator cartridge, solvents evaporated to give a brown oil. The crude product was purified by flash silica chromatography using elution gradient 0 to 100% ethyl acetate in isohexane to afford the subtitled compound (1 g) as a gum. MS [M+H-C4H9]+=303 (MultiMode+) 1H NMR (400 MHz, CDCl3) δ 7.76 (s, 1H), 7.63 (s, 1H), 7.34-7.30 (m, 2H), 7.26 (t, J=8.0 Hz, 1H), 7.09-7.05 (m, 1H), 4.11 (t, J=7.2 Hz, 2H), 3.70 (t, J=6.5 Hz, 2H), 3.68 (t, J=7.2 Hz, 2H), 2.89 (t, J=7.2 Hz, 2H), 2.49 (t, J=6.4 Hz, 2H), 1.93 (sextet, J=7.2 Hz, 2H), 1.43 (s, 9H), 0.95 (t, J=7.3 Hz, 3H)

Provenance & Evidence