4'-Fluoroacetophenone → HCID 68901665, compound

Participants

Reaction Steps

A mixture of 2-amino-5-bromonicotinaldehyde [prepared by the method of Duggan et al., WO 9818461] (5.53 g, 27.5 mmol), 4-fluoroacetophenone (3.0 mL, 24.8 mmol) and 20% aqueous potassium hydroxide (3.5 mL) in ethanol (400 mL) was heated at reflux for 1 hour. The reaction mixture was allowed to stand at room temperature, the crystals formed collected under suction, washed with ethanol and dried in vacuo to afford 6-bromo-2-(4-fluorophenyl)-1,8-naphthyridine (4.86 g, 65%). 1H NMR (500 MHz, CDCl3) δ 9.12 (1H, d, J 2.5 Hz), 8.34 (1H, d, J 2.5 Hz), 8.32-8.28 (2H, m), 8.18 (1H, d, J 8.5 Hz), 7.99 (1H, d, J 8.5 Hz), 7.25-7.19 (2H, m).

Provenance & Evidence