Cl[C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>COCCOC.O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:11]([CH2:12][OH:13])=[CH:10]2A mixture of (2-chloro-8-methylquinolin-3-yl)methanol (413 mg, 2.0 mmol) and K2CO3 (828 mg, 6.0 mmol) in DME (7.5 mL) and water (7.5 mL) was degassed (×3). Phenylboronic acid (293 mg, 2.4 mmol), PPh3 (21 mg, 0.08 mmol) and Pd(OAc)2 (4.5 mg, 0.02 mmol) were added, the mixture was degassed, then heated at reflux for 75 minutes. The reaction mixture was allowed to cool to r.t. then extracted with EtOAc (2×20 mL). The combined organic phases were washed with water (20 mL), dried (MgSO4) and evaporated in vacuo. The residue was purified by column chromatography (SiO2, 10-100% EtOAc in heptane) then by preparative HPLC (Method 1). The product obtained was partitioned between EtOAc and 10% aqueous K2CO3 solution. The organic phase was dried (MgSO4) and evaporated in vacuo to give the title compound (241 mg, 49%) as a white solid. δH (CDCl3) 8.31 (s, 1H), 7.68-7.76 (m, 3H), 7.41-7.59 (m, 5H), 4.86 (d, J 5.1 Hz, 2H), 2.82 (s, 3H), 1.85 (t, J 5.5 Hz, 1H). LCMS (ES+) 250.1 (M+H)+, RT 3.52 minutes (Method 3).
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