Sodium Carbonate → HCID 57581528, compound

Participants

Reaction Conditions

Reaction Steps

(R)-tert-butyl 4-(4-chlorophthalazin-1-yl)-2-methylpiperazine-1-carboxylate (0.500 g, 1.38 mmol), phenylboronic acid (0.168 g, 1.38 mmol), and tetrakis(triphenylphosphine)palladium (0) (79.9 mg, 0.069 mmol) were placed in a flask under argon. Degassed toluene (15 mL) and aqueous sodium carbonate (2.0 M, 1.5 mL) were added and the reaction heated at 100° C. for 22 hours. The reaction was allowed to cool before being added to 80 mL aqueous K2CO3 (10%). The aqueous phase was extracted with dichloromethane three times, and the combined organics were dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-70% ethyl acetate gave an off-white solid. 1H-NMR (500 Mhz) δ 1.17 (br d, J=5.5 Hz, 3H), 1.44 (s, 9H), 3.40-3.65 (series of m, 5H), 3.82 (m, 1H), 4.06 (m, 1H), 7.47 (m, 3H), 7.69 (m, 3H), 7.78 (td, J=6.7, 1.2 Hz, 1H), 7.97 (d, J=7.9 Hz, 1H), 8.09 (d, J=8.5 Hz, 1H).

Provenance & Evidence