Sodium Carbonate → (R)-(4-(4-(4-(hydroxymethyl)phenyl)phthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

Participants

Reaction Conditions

Reaction Steps

(R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone (JK-5) (150 mg, 0.409 mmol), 4-(hydroxymethyl)phenylboronic acid (93.2 mg, 0.613 mmol), and tetrakis(triphenylphosphine)palladium (0) (23.6 mg, 0.023 mmol) were dissolved in toluene (4 mL) and aqueous sodium carbonate (2.0 M, 0.400 mL) under an atmosphere of argon. The reaction was heated at 100° C. for 15 hours, then cooled and taken up in ethyl acetate (80 mL). After washing with aqueous K2CO3 (10%), water, and then saturated sodium chloride, the organics were dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-100% ethyl acetate gave a pale yellow solid, JK-28. MS (M+H)+=439.2.

Provenance & Evidence