To a solution of (2-chloro-8-methylquinolin-3-yl)methanol (250 mg, 1.20 mmol) in DME (4 mL) and water (1 mL) was added 2-methoxybenzeneboronic acid (200 mg, 1.32 mmol), potassium phosphate tribasic (306 mg, 1.44 mmol) and Pd(PPh3)4 (69 mg, 0.06 mmol). The reaction mixture was heated to 120° C. under microwave irradiation for 1 h. The product was diluted with EtOAc (40 mL) and washed with water (10 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo to give a yellow oil, which was purified by column chromatography (SiO2, 30% EtOAc in heptane) to give a yellow foam. To a solution of this product (200 mg) in DCM (10 mL) was added phosphorus tribromide (0.13 mL, 1.43 mmol) and the mixture was stirred at r.t. for 2 h. The mixture was partitioned between DCM (75 mL) and aqueous NaHCO3 solution (20 mL). The organic layer was washed with water (20 mL), separated, dried (MgSO4) and the solvent removed in vacuo to give a yellow oil. To a solution of this oil (200 mg) in DMF (10 mL) was added K2CO3 (89 mg, 0.64 mmol) and 6-mercaptopurine (109 mg, 0.64 mmol) and the reaction mixture was stirred at r.t. for 18 h. The reaction mixture was diluted with EtOAc (150 mL) and washed with water (7×30 mL). The organic layer was separated, dried (MgSO4) and the solvent removed in vacuo to give a colourless oil. Trituration in DCM/diethyl ether gave the title compound (112 mg, 22%) as an off-white solid. δH (DMSO-d6) 13.50 (br s, 1H), 8.63 (s, 1H), 8.46 (s, 1H), 8.42 (s, 1H), 7.80 (d, J 9 Hz, 1H), 7.58-7.60 (m, 1H), 7.35-7.50 (m, 3H), 7.02-7.16 (m, 2H), 4.60-4.70 (m, 2H), 3.78 (s, 3H), 2.65 (s, 3H). LCMS (ES+) 414.2 (M+H)+, RT 3.40 minutes (Method 3).
