Potassium Carbonate → HCID 67201028, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2,5-dichloro-8-methylquinolin-3-yl)methanol (500 mg, 2.06 mmol), o-tolylboronic acid (337 mg, 2.48 mmol) and K2CO3 (428 mg, 3.09 mmol) in DME (8 mL) and water (2 mL) was degassed by bubbling N2 through it for 5 minutes. Pd(PPh3)4 (119 mg, 0.1 mmol) was added and the reaction mixture was degassed for a further 5 minutes and then heated to 120° C. under microwave irradiation for 1 h. The solvent was removed in vacuo and the product was dissolved in DCM (40 mL). To this solution was added phosphorus tribromide (1.34 mL, 14.23 mmol) and the reaction mixture was stirred at r.t. for 3 h. The mixture was partitioned between DCM (100 mL) and 10% aqueous K2CO3 solution (50 mL). The organic layer was separated, dried (MgSO4) and the solvent removed in vacuo. The product obtained was dissolved in DMF (10 mL) and to this solution was added K2CO3 (147 mg, 1.06 mmol) and 6-mercaptopurine (180 mg, 1.06 mmol). The reaction mixture was stirred at r.t. for 18 h. The mixture was diluted with EtOAc (150 mL) and was washed with water (7×50 mL). The organic layer was separated, dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (SiO2, 0-5% MeOH in DCM), then by preparative HPLC (Method 1), gave the title compound (149 mg, 16%) as an off-white solid. δH (DMSO-d6) 13.48 (br s, 1H), 8.86 (s, 1H), 8.62 (s, 1H), 8.43 (s, 1H), 7.66 (d, J 9 Hz, 1H), 7.59 (d, J 9 Hz, 1H), 7.35 (m, 4H), 4.68 (br s, 2H), 2.62 (s, 3H), 2.12 (s, 3H). LCMS (ES+) 432.2, 434.1 (M+H)+, RT 4.25 minutes (Method 3).

Provenance & Evidence