2-Isothiocyanatopyridine → HCID 89783777, compound

Participants

Reaction Steps

A mixture of 2-amino-3-bromobenzoic acid (705 mg, 3.26 mmol, Sigma Aldrich) and 2-isothiocyanatopyridine (800 mg, 5.87 mmol, 415a) in EtOH (19.6 mL) was set stirring at RT, and TEA (0.68 mL, 4.90 mmol) was added dropwise. It was sealed and heated to 100° C. for 16 h. The mixture was concentrated under reduced pressure to a residue that was taken up in DCM. Silica was added, and the crude reaction was adsorbed. It was purified on 24 g SiO2 (eluent: 0-100% EtOAc/hexanes over 30 min, RediSep Gold). The product fractions were combined and concentrated under reduced pressure to give a yellow-orange solid (311 mg, 29%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.18 (1H, br. s.) 8.60 (1H, d, J=4.69 Hz) 8.39 (1H, d, J=4.11 Hz) 8.11 (1H, d, J=6.85 Hz) 7.83-7.93 (1H, m) 7.78 (1H, dd, J=7.82, 1.37 Hz) 7.44-7.53 (2H, m). m/z (ESI, +ve) 333.8 (M+H)+.

Provenance & Evidence