Potassium Carbonate → HCID 44126369, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-chloro-8-methylquinolin-3-yl)methanol (250 mg, 1.21 mmol), pyridine-3-boronic acid (178 mg, 1.45 mmol) and K2CO3 (250 mg, 1.81 mmol) in DME (4 mL) and water (0.4 mL) was degassed for 5 minutes. Pd(PPh3)4 (70 mg, 0.06 mmol) was added and the reaction mixture was degassed for a further 5 minutes and heated to 120° C. under microwave irradiation for 1 h. The solvent was removed in vacuo and the product obtained was dissolved in DCM (19 mL). Phosphorus tribromide (0.83 mL, 8.8 mmol) was added to the mixture, which was stirred at r.t. for 90 minutes. The mixture was partitioned between DCM (50 mL) and 10% aqueous K2CO3 solution (30 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo. The product obtained was dissolved in DMF (5 mL) and to the mixture was added K2CO3 (64 mg, 0.46 mmol) and 6-mercaptopurine (78 mg, 0.46 mmol). After stirring at r.t. for 18 h, the reaction mixture was diluted with EtOAc (150 mL) and washed with water (7×50 mL). The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo. Purification by column chromatography (SiO2, 1-10% MeOH in DCM) gave the title compound (49 mg, 10%) as an off-white solid. δH (DMSO-d6) 13.51 (br s, 1H), 8.92-8.94 (m, 1H), 8.62-8.65 (m, 1H), 8.61 (s, 1H), 8.58 (s, 1H), 8.40 (s, 1H), 8.18 (d, J 7.7 Hz, 1H), 7.85 (d, J 7.7 Hz, 1H), 7.50-7.66 (m, 3H), 4.86 (s, 2H), 2.70 (s, 3H). LCMS (ES+) 385.1 (M+H)+, RT 2.45 minutes (Method 3).

Provenance & Evidence