Triethylamine → HCID 69206519, compound

Participants

Reaction Steps

Under a N2 atmosphere, 1.02 g (3.36 mmol) of an (E/Z) mixture of 2-chloro-N-[3-(6-methoxy-pyridin-3-yl)-allyl]-nicotinamide, 995 mg (3.36 mmol) of tetrabutylammonium chloride, 1240 mg (3.36 mmol) of tetrabutylammonium iodide and 80 mg (0.36 mmol) of palladium diacetate are dissolved in 63 ml of DMF, then 1.2 ml (8.6 mmol) of triethylamine are added and stirring effected for 28 h at 150° C. in an ampulla. After adding a further 80 mg of palladium diacetate, stirring is again effected for 24 h at 150° C. The mixture is filtered and the DMF is partially evaporated on a RE. The residue is dissolved with EtOAc and diluted Na2CO3 solution, the water phase separated and extraction effected twice more with EtOAc/EtOH 9:1. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2, methylene chloride/EtOAc 1:1→EtOAc) yields 8-[(6-methoxy-pyridin-3-yl)-methyl]-6H-[1,6]naphthyridin-5-one A (contaminated with ca. 25% 8-[1-(6-methoxy-pyridin-3-yl)-methylidene]-7,8-dihydro-6H-[1,6]naphthyridin-5-one B); FAB-MS: (M+H)+=268; HPLC(gradient20-100) tRet=6.0/8.3; 1H NMR (CDCl3) i.a. δ4.12 (s, H2C—C(8) of A), 4.71 (d, 2.3 Hz, H2C(7) of B).

Provenance & Evidence