Tricyclohexylphosphine → 1-o-Tolylphthalazin-6-ylboronic acid

Participants

Reaction Conditions

Reaction Steps

In a sealed glass tube, a mixture of 6-chloro-1-o-tolylphthalazine (127 mg, 0.50 mmol), bis(pinacolato)diboron (146 mg, 0.57 mmol), potassium acetate (98 mg, 1.0 mmol), tris(dibenzylideneacetone)dipalladium (18 mg, 20 μmol) and tricyclohexylphosphine (11 mg, 40 μmol) in 1,4-dioxane (2 mL) was heated in a Personal Chemistry microwave at 125° C. for 30 min. The reaction mixture was filtered through a pad of Celite, and rinsed with ethyl acetate (5 mL). The filtrate was concentrated, then treated with 2 N aq. HCl (2 mL), and extracted with hexanes (5 mL). The acidic layer was diluted with 1 mL of DMSO and put on a reversed phase HPLC (5-90% [0.1% TFA in acetonitrile] in [0.1% TFA in water]) to provide 1-o-tolylphthalazin-6-ylboronic acid as a white fluffy solid. MS (ESI, pos. ion.) m/z: 255 (M+1).

Provenance & Evidence