Sodium Carbonate → HCID 22285307, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 2,5-dichloro-[1,8]naphthyridine (Barlin, G. B.; Tan, W.-L. Aust. J. Chem. 1984, 37, 1065) (0.1029 g, 0.513 mmol) and 2-fluorobenzeneboronic acid (72.4 mg, 0.517 mmol) in 2 N aqueous sodium carbonate (0.620 mL, 1.24 mmol) and ethylene glycol dimethyl ether (3 mL) was degassed by bubbling nitrogen through for 15 min. Tetrakis-(triphenylphosphine)palladium(0) (29.9 mg, 0.0259 mmol) was added and the mixture was degassed for a further 10 min, then heated at 80° C. for 16 h under nitrogen. The mixture was partitioned between water (20 mL) and dichloromethane (20 mL). The aqueous layer was further extracted with dichloromethane (2×20 mL), and the combined organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 15% EtOAc/CH2Cl2, to afford 0.1216 g (91%) of the title compound as an off-white solid. δH (360 MHz, CDCl3) 7.22 (1H, dd, J 11.8 and 8.2), 7.34 (1H, td, J 7.7, 0.7), 7.49 (1H, tdd, J 7.4, 5.3, and 2.1), 7.58 (1H, d, J 4.7), 8.18 (1H, dd, J 8.8, 2.5), 8.39 (1H, td, J 7.7, 1.8), 8.66 (1H, d, J 8.8), 9.03 (1H, d, J 4.8).

Provenance & Evidence