3-Fluorobenzylamine → HCID 76285218, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(ethylthio)-4-methyl-7-(trifluoromethyl)-1,5-naphthyridine-3-carboxylate (0.20 g, 0.58 mmol, 1 eq.) in toluene (6 ml) were added Me3Al(2M solution in toluene, 1.16 ml, 2.32 mmol, 4 eq.) and (3-fluorophenyl)methanamine (0.27 ml, 2.32 mmol, 4 eq.) at RT. The reaction mixture was stirred at 110° C. for 16 h. Afterwards the mixture was diluted with water (50 ml) and was extracted with EtOAc (3×40 ml). The combined organic layers were washed with a 0.5 M aq. HCl (60 ml), brine (60 ml), dried over anhydrous Na2SO4 and evaporated to provide the crude product, which was purified by CC (EtOAc/hexane 1:4) to yield 2-Ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-7-(trifluoromethyl)-[1,5]naphthyridine-3-carboxylic acid amide (example 1) (0.14 g, 0.33 mmol, 57%). MS m/z [M+H]+ 424.1.

Provenance & Evidence