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

Participants

Reaction Conditions

Reaction Steps

(R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(cyclohexyl)methanone (JK-21) (150 mg, 0.402 mmol), 4-(hydroxymethyl)phenylboronic acid (85.6 mg, 0.563 mmol), and tetrakis(triphenylphosphine)palladium (0) (23.6 mg, 0.0201 mmol) were dissolved in toluene (5 mL) and aqueous sodium carbonate (2.0M, 0.500 mL) under an atmosphere of argon. The reaction was heated at 100° C. for 23 hours, then cooled and taken up in ethyl acetate (80 mL). After washing with aqueous K2CO3 (10%), water, and 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-29. MS (M+H)+=445.4.

Provenance & Evidence