Potassium Carbonate → HCID 58292550, compound

Participants

Reaction Steps

A mixture of [6-(6-Chloro-pyridazin-3-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.5 g, 1.37 mmol), 10% Pd/C (0.45 g) and K2CO3 (0.38 g, 2.75 mmol) in EtOAc (20 mL) was hydrogenated at 30 psi for 2 hours. The mixture was filtered through a pad of celite and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (DCM:MeOH 95:5) to give [1-hydroxy-4-methyl-6-(pyridazin-3-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.35 g, 77%). 1H NMR (400 MHz, DMSO): δ 9.26 (s, 1H), 8.98 (dd, J=1.6, 4.8 Hz, 1H), 7.76-7.73 (m, 1H), 7.44 (dd, J=1.2, 8.8 Hz, 1H), 7.26 (d, J=2.4 Hz, 1H), 7.12 (d, J=1.6 Hz, 1H), 5.53 (dd, J=2.4, 9.2 Hz, 1H), 4.03 (q, J=7.2 Hz, 2H), 3.14 (dd, J=2.8, 15.6 Hz, 1H), 2.33-2.24 (m, 1H), 2.30 (s, 3H), 1.13 (t, J=7.2 Hz, 3H). MS (ESI) m/z=329 [M+H]+.

Provenance & Evidence