m-Toluidine → HCID 69320816, compound

Participants

Reaction Conditions

Reaction Steps

In a microwave vial, 4-chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile (0.200 g, 0.963 mmol) and m-toluidine (0.11 mL, 0.11 g, 1.1 mmol) were taken up in 5 mL DME. The vial was crimp-sealed and heated in a microwave reactor at 140° C. for 10 minutes. 3-(aminomethyl)pyridine (2.0 mL, 2.1 g, 19 mmol) was then added, and the reaction was heated at 200° C. for 30 minutes. To work up the reaction, the vial contents were partitioned between EtOAc and brine. The aqueous layer was extracted with additional EtOAc, and the combined organic extracts washed with water and evaporated. The crude product was purified twice by preparative HPLC, and lyophilized to give a fluffy, bright yellow solid (7.5 mg, 2.1% yield): 1H NMR (400 MHz, DMSO-D6) δ 2.31 (s, 3 H) 4.55 (d, J=4.0 Hz, 2 H) 7.06 (s, 3 H) 7.16 (s, 1 H) 7.21-7.39 (m, 2 H) 7.44 (s, 1 H) 7.75 (d, J=7.6 Hz, 1 H) 8.22 (s, 1 H) 8.43 (s, 1 H) 8.59 (s, 1 H) 8.82 (s, 1 H) 9.61 (br s, 1 H).

Provenance & Evidence