2-Fluoroaniline → HCID 62155572, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-Amino-5-bromo-nicotinic acid (1 g, 4.61 mmol) and SOCl2 (5 mL) in toluene (15 mL) was stirred at 130° C. for 2 h. After concentrated, the residue was dissolved in tetrahydrofuran (20 mL), and then 2-fluoro-phenylamine (1.09 g, 9.81 mmol) was added dropwise at 0° C. The reaction mixture was heated to 90° C. for 4 h. After being cooled to room temperature and quenched with saturated aqueous K2 CO3 (10 mL), the mixture was extracted with ethyl acetate (50 mL*3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with silica gel column chromatograph (PE:EtOAc=2:1) to give 2-amino-5-bromo-N-(2-fluorophenyl)nicotinamide (1.0 g, 70% yield) as yellow solid. 1H-NMR (CDCl3, 400 MHz) δ 8.25˜8.28 (m, 2H), 7.86 (d, J=2.4 Hz, 2H), 7.13˜7.22 (m, 3H), 6.36 (s, 2H). MS (M+H)+: 311/313.

Provenance & Evidence