Potassium Carbonate → HCID 67198434, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2-chloro-8-methylquinolin-3-yl)methanol (250 mg, 1.21 mmol) in DME (4 mL) and water (0.4 mL) was added 4-fluorophenylboronic acid (203 mg, 1.45 mmol) and K2CO3 (250 mg, 1.81 mmol). The mixture was degassed by bubbling through N2 for 5 minutes before adding Pd(PPh3)4 (70 mg, 0.06 mmol) and degassing for a further 5 minutes. The reaction mixture was heated to 120° C. under microwave irradiation for 1 h. The mixture was diluted with EtOAc (100 mL) and washed with water (30 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo. Purification by column chromatography (SiO2, 0-50% EtOAc in heptane) gave a white solid. To a solution of this solid (230 mg) in DCM (10 mL) was added phosphorus tribromide (0.4 mL, 4.31 mmol) and the mixture was stirred at r.t. for 90 minutes. The mixture was partitioned between DCM (100 mL) and 10% aqueous K2CO3 solution (30 mL). The organic layer was separated, dried (MgSO4) and the solvent removed in vacuo to give a white solid. To a solution of this solid in DMF (30 mL) was added potassium carbonate (352 mg, 2.55 mmol) and 6-mercaptopurine (433 mg, 2.55 mmol). The reaction mixture was stirred at r.t. for 18 h. The mixture was diluted with EtOAc (100 mL) and washed with water (7×40 mL). The organic layer was separated, dried (MgSO4) and the solvent removed in vacuo to give the title compound (217 mg, 45%) as a white solid. δH (DMSO-d6) 13.54 (br s, 1H), 8.63 (s, 1H), 8.57 (s, 1H), 8.42 (s, 1H), 7.75-7.83 (m, 3H), 7.60-7.65 (m, 1H), 7.45-7.55 (m, 1H), 7.30-7.38 (m, 2H), 4.85 (s, 2H), 2.69 (s, 3H). LCMS (ES+) 402.2 (M+H)+, RT 3.79 minutes (Method 3).

Provenance & Evidence