4'-Fluoro-2'-nitroacetanilide → N-(4-Fluoro-1H-indol-7-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

4-Fluoro-2-nitroacetanilide (1 eq.) was dissolved in dry THF. After the solution was cooled down to −78° C., an excess of vinyl magnesium bromide (3-4 eq.) was added. Then, the reaction was kept below −40° C. for two hours before quenched with 20% NH4Cl. The aqueous phase was extracted with EtOAc. The combined organic layer was dried over MgSO4. After filtration and concentration, the crude product was purified by silica gel column chromatography to afford N-(4-fluoro-1H-indol-7-yl)acetamide. MS m/z: (M+H)+ calc'd for C10H10FN2O: 193.08. Found 193.09. HPLC retention time: 1.29 minutes (column E, solvent system II).

Provenance & Evidence