Allyl iodide → HCID 68816871、化合物

反応式

[F:1][C:2]1[CH:3]=[N+:4]([O-:13])[C:5]2[CH:6]=[CH:7][C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](I)[CH:21]=[CH2:22]>CN(C=O)C>[F:1][C:2]1[CH:3]=[N+:4]([O-:13])[C:5]2[CH:6]=[CH:7][C:8](=[O:12])[N:9]([CH2:22][CH:21]=[CH2:20])[C:10]=2[CH:11]=1

参加物

実験手順

Crude 7-fluoro-1,5-naphthyridin-2(1H)-one 5-oxide (0.995 g, 5.524 mmol) and potassium carbonate were stirred in anhydrous DMF (20 mL) under argon, and allyl iodide (1.5 mL, ca. 3 eq.) was added. The mixture was stirred at rt overnight. The solvent was removed under reduced pressure and the residue was partitioned between DCM (100 mL) and water (50 mL). The organic phase was separated using a hydrophobic frit and the aqueous phase was extracted with DCM (2×50 mL). The combined organic extracts were dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to give the crude product as a brown gum. This was purified by column chromatography on silica gel eluted with 0-10% methanol in DCM. Appropriate fractions were combined and evaporated under reduced pressure to give 7-fluoro-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one 5-oxide (0.341 g) as a tan amorphous solid.