1-methyl-N-[2-(6-methoxy-2-naphthyl)-2-oxoethyl]-1H-indole-3-carboxamide → 3-[5-(6-methoxy-2-naphthyl)-1,3-oxazol-2-yl]-1-methyl-1H-indole

Participants

Reaction Steps

1-Methyl-N-[2-(6-methoxy-2-naphthyl)-2-oxoethyl]-1H-indole-3-carboxamide (3.68 g 2.68 mmol), prepared in the previous step, in 200 mL of POCl3 was refluxed for 4 h. As the reaction cooled to room temperature a solid precipitated. The solid was collected by filtration, rinsed with 10 mL of methylene chloride and dried under reduced pressure. The solid was then taken up in 80% CH2Cl2/CH3OH, extracted three times with 5% NaHCO3, dried (MgSO4), filtered and the solvent was removed under reduced pressure to give 3-[5-(6-methoxy-2-naphthyl)-1,3-oxazol-2-yl]-1-methyl-1H-indole (2.38 g, 68%) as a light yellow solid, mp 187-189° C. Elemental Analysis for C23H18N2O2 Calc'd: C, 77.95; H, 5.12; N, 7.90. Found: C, 77.16; H, 5.10; N, 7.77.

Provenance & Evidence