Triethylsilane → 4-{3-[(Hydroxyimino)methyl]-2-methyl-1H-indol-1-yl}phenol

Participants

Reaction Steps

To a stirred solution of dichloromethane (20 mL), Pd(OAc)2 (50 mg, 0.2 mmol), and triethylsilane (2 mL) was added triethylamine (1 mL), and the mixture was stirred at room temperature for 15 min. To the mixture was added 1-(4-benzyloxyphenyl)-2-methyl-1H-indole-3-carbaldehyde oxime (0.36 g, 1 mmol) in dichloromethane (10 mL), and stirred for 90 min. Ethyl acetate (25 mL) and ammonium chloride (25 mL of 10% solution) were added and the product extracted into ethyl acetate (2×25 mL). The combined organic layers were washed with water (3×25 mL) and brine (25 mL) and dried over MgSO4. After removing the solvent, a liquid was obtained, which was dissolved in anhydrous tetrahydrofuran (10 mL). To this mixture was added tetrabutyl ammonium fluoride (3 mL). After stirring for 30 min, the mixture was extracted with ethyl acetate and water. The organic layer was washed with water and brine and dried over MgSO4. After evaporation of the solvent afforded the crude solid which was purified by silica gel chromatography (25% ethyl acetate-hexanes) to give a pale yellow solid (83%): mp 171-173° C.; 1H NMR (DMSO-d6): δ 2.29 (3H, s), 6.95 (4H, d, J=7.7 Hz), 7.09-7.13 (2H, m), 7.22 (2H, d, J=8.7 Hz), 7.98-8.01 (1 H, m), 8.40 (1H, s), 9.89 (1H, s), 10.63 (1H, s); MS m/z (M+H)+ 267. Anal. for C16H14N2O2: Calc'd: C, 72.17; H, 5.30; N, 10.52. Found: C, 71.78; H, 5.23; N, 10.37.

Provenance & Evidence