Triethylsilane → HCID 73060097, compound

Participants

Reaction Steps

To a stirred solution of dichloromethane (10 mL), Pd(OAc)2 (50 mg, 0.2 mmol), and triethylsilane (3 mL) was added triethylamine (1.5 mL), and the mixture was stirred at ambient temperature for 15 min. To the mixture was added 1-(4-benzyloxy-3-fluorophenyl)-2-methyl-1H-indole-3-carbaldehyde oxime (0.52 g, 1.4 mmol) in dichloromethane (15 mL), and stirring was continued for 4 hr. 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 organics 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 stirring mixture was added tetrabutyl ammonium fluoride (3 mL). After stirring for 30 min., the mixture was taken up in ethyl acetate/water and shaken and the layers separated. The organic portion was washed with water and brine and dried over MgSO4. After evaporation of the solvent, the crude solid was purified by silica gel chromatography (25% ethyl acetate-hexanes) to give a pale yellow solid (0.22 g, 56%): mp 182-184° C.; 1H NMR (DMSO-d6): δ 2.31 (3H, s), 6.98-7.01 (1H, m), 7.07-7.17 (4H, m), 7.35 (1H, dd, J=11.7 Hz, J=2.4 Hz), 7.99-8.03 (1H, m), 8.40 (1H, s), 10.35 (1H, br s), 10.64 (1H, s); MS m/z (M+H)+ 285: Anal. for C16H13FN2O2 (0.3H2O): Calc'd: C, 66.34; H, 4.57 N, 9.30. Found: C, 66.38; H, 4.61; N, 9.85.

Provenance & Evidence