Lithium aluminum hydride → HCID 58368422, compound

Participants

Reaction Steps

To a mixture of methyl 5-bromo-8-(3-fluorophenyl)quinoline-7-carboxylate (0.360 g, 1.00 mmol, from Example 10, Step 4) in tetrahydrofuran (1 mL) was added 1.0 M lithium tetrahydroaluminate in tetrahydrofuran (1.00 mL, 1.00 mmol) at 0° C. The reaction was stirred at room temperature for 30 minutes then quenched by successive addition of 0.038 mL of water, 0.038 mL of 15% NaOH, 0.11 mL of water. After stirred for 30 minutes, the mixture was filtered. The filtrate was dried over magnesium sulfate and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 80% ethyl acetate in hexane, to give the desired product (150 mg, 45%). LCMS calculated for C16H12BrFNO (M+H)+: m/z=332.0; Found: 332.0.

Provenance & Evidence