Dichloromethane → Diisopropylethylamine

Trifluoroacetic acid (2.35 mL) was added at 0° C. to a dichloromethane (9.38 mL) solution of the tert-butyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate (469 mg, 0.988 mmol) produced in Example 1, and the mixture was stirred at room temperature for 1 hour. From the reaction solution, the solvent was then distilled off. To a THF (450 μL) solution of a portion (150 mg) of the obtained residue and diisopropylethylamine (431 μL, 2.48 mmol), a THF (3.0 mL) solution of the preceding produced acid chloride compound was added at 0° C., and the mixture was stirred at room temperature for 3 hours. To the reaction solution, a saturated aqueous solution of ammonium chloride and water were added, followed by extraction with ethyl acetate three times. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by preparative thin-layer silica gel chromatography (hexane:ethyl acetate=1:2, V/V) to obtain the title compound as white foam (13 mg, yield: 11%).

1. distillationFrom the reaction solution, the solvent was then distilled off

ORD record

ord-76b310a2b25a4567a798440c242d29ff

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232287B2