Triethylamine → 4-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid 1-tert-butoxycarbonyl-pyrrolidin-3-yl ester

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Reaction Steps

3-Hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.37 g, 2 mmol) was dissolved in 4 mL of DCM with triethylamine (0.28 mL, 2 mmol). 4-Nitro-benzoyl chloride (0.4 g, 2 mmol) was added and the mixture was stirred at room temperature for 12 h. It was then diluted with DCM and washed with saturated NaHCO3 (3×20 mL). The organic layer was dried, filtered and evaporated. The residue was dissolved in DCM (4 mL) with triethylamine (0.36 mL, 2.6 mmol) and 4b (0.49 g, 1.3 mmol) was added. The mixture was stirred at room temperature for 8 h, diluted with DCM and washed with saturated NaHCO3. The organic layer was evaporated to afford 21a, LCMS 588.2 (MH+).

Provenance & Evidence