Triethylsilane → HCID 68754450, compound

Participants

Reaction Steps

Under an argon atmosphere, to an ice-cooled solution of ethyl 2-[hydroxy(6-methoxy-2-phenyl-1H-indol-3-yl)methyl]thiazole-4-carboxylate (69.0 mg) and triethylsilane (0.135 mL) in methylene chloride (1.7 mL) was slowly added dropwise a boron trifluoride diethyl ether complex (0.107 mL). After stirring for 10 minutes, the mixture was stirred at room temperature for additional 15 minutes. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (17.0 mg). 1H-NMR (CDCl3) δ ppm: 1.43 (3H, t, J=7.2 Hz), 3.87 (3H, s), 4.45 (2H, q, J=7.2 Hz), 4.61 (2H, s), 6.79 (1H, dd, J=2.1, 8.7 Hz), 6.93 (1H, d, J=2.1 Hz), 7.30-7.60 (6H, m), 7.99 (1H, s), 8.13 (1H, br s).

Provenance & Evidence