Phosphorus oxychloride → 6-(Morpholine-4-carbonyl)-1H-indole-3-carbaldehyde

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Reaction Steps

A solution of (1H-indol-6-yl)(morpholino)methanone (200 mg, 0.869 mmol, 1.0 eq) in DMF (3.0 ml) was added dropwise at 0° C. to phosphorus oxychloride (0.34 mL, 2.60 mmol, 3.0 eq) in DMF (5.0 mL) under stirring. The mixture was stirred at room temperature for 3 h, then neutralized with saturated sodium hydrogen carbonate solution, diluted with water (20 mL), and extracted with ethyl acetate (2×10 mL). The organic layers were combined, washed with brine (20 mL), dried over sodium sulfate and evaporated. The residue was purified by silica gel column chromatography [100-200 mesh; methanol/dichloromethane=1:9]. White solid. Yield: 100 mg (45% of theory).

Provenance & Evidence