Dichloromethane → ethyl 2-(7-acetamido-4-fluoro-1H-indol-3-yl)-2-oxoacetate

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Reaction Steps

N-(4-fluoro-1H-indol-7-yl)acetamide (1 eq.) was added to a suspension of AlCl3 (1 eq.) in CH2Cl2 (100 ml). After 15 min, a premixed suspension of AlCl3 (2 eq.) and ClCOCOEt (2 eq.) in CH2Cl2 was added and stirring was continued at room temperature for 1 hour before iced saturated NaHCO3 solution was added. 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 ethyl 2-(7-acetamido-4-fluoro-1H-indol-3-yl)-2-oxoacetate. MS m/z: (M+H)+ calc'd for C14H14FN2O4:293.09. Found 293.11. HPLC retention time: 0.98 minutes (column E, solvent system II). 1H NMR (300 MHz, CD3OD) 8.32 (s, 1H), 7.16 (m, 1H), 6.94 (m, 1H), 4.43 (q, 2H, J=7.2 Hz), 2.24 (s, 3H), 1.39 (t, 3H, J=7.2 Hz).

Provenance & Evidence