Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.[C:13]1([CH3:22])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.[OH-].[Na+]>C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.C(O)C>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH3:22])=[N:3][N:4]=[CH:5]2
A mixture of 1,6-dichlorophthalazine (1.04 g, 5.21 mmol), tetrakis(triphenylphosphine)palldium (0.30 g, 0.26 mmol), o-tolylboronic acid (0.57 g, 4.2 mmol) in 2 N aq. sodium carbonate (5 mL), 1,4-dioxane (5 mL) and ethanol (2.5 mL) was heated in a Personal Chemistry microwave at 78° C. for 45 min. The mixture was treated with 1 N sodium hydroxide (10 mL), extracted with ethyl acetate (2×35 mL). The combined ethyl acetate layers were dried and concentrated. Purification on an ISCO column (40 g, eluted with 30-75% ethyl acetate in hexanes) provided 6-chloro-1-o-tolylphthalazine as a brown amorphous solid. MS (ESI, pos. ion.) m/z: 255 (M+1).
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