Tetrahydrofuran → HCID 178525208, compound

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Reaction Steps

To an oven-dried flask was added 4-[[10-(17H-tetrabenzo[a,c,g,i]fluoren-17-yl)-decyl]oxy]phenyl]-methyl 2,4,5-trifluoro-β-oxobenzenepropanoate (6) (122.5 mg, 0.148 mmol) and dissolved in freshly distilled THF (10 mL). The flask was purged with nitrogen and N,N-dimethylformamide diethyl acetal was added as a solution in THF (1 mL) via syringe. Glassware was washed with THF (2 mL). The solution was stirred at room temperature under an atmosphere of nitrogen for 24 hours. Cyclopropylamine (120.2 mg, 0.818 mmol) was added as a solution in THF (1 mL) and the resultant solution stirred at room temperature under nitrogen for 72 hours. The solution was quenched by the addition of saturated ammonium chloride solution (20 mL) and organic products extracted faith DCM (2×20 mL), dried over MgSO4 and solvent removed in vacuo to yield a dark yellow oil. This was purified by flash column chromatography using DCM as eluent to yield [4-[[10-(17H-tetrabenzo[a,c,g,i]fluoren-17-yl)-decyl]oxy]phenyl]methyl α-[(cyclopropylamino)-methylene]-2,4,5-trifluoro-β-oxobenzenepropanoate as a pale yellow solid (45.1 mg, 0.051 mmol, 34%).

Provenance & Evidence