Potassium Acetate → HCID 67271785, compound

Participants

Reaction Conditions

Reaction Steps

Potassium acetate (54.3 g, 44 mmol), pinacol diboron (5.5 g, 22 mmol) and PdCl2(dppf) (0.60 mg, 0.73 mmol) were added sequentially to a solution 1-(4-methoxybenzyl)-6-bromoquinolin-2(1H)-one (5.0 g, 15 mmol) in DMF (70 mL). After flushing with N2, the reaction vessel was sealed and heated at 80° C. for 14 h and then partitioned between H2O and EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) concentrated and purified via column chromatography to yield 1-(4-methoxybenzyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2(1H)-one (38 g, 67% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 8.04 (brs, 1H), 7.86 (dd, J=1.2, and 8.4 Hz, 1H), 7.76 (d, J=9.6 Hz, 1H), 7.32 (d, J=9.2 Hz, 1H), 7.17 (d, J=8.4 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 6.80 (d, J=9.6 Hz, 1H), 5.52 (brs, 2H), 3.77 (s, 3H), 1.36 (s, 12H); LC-MS (EI) m/z: 392.3 (M+H+).

Provenance & Evidence