Sodium hydride → 4-[6-(5-Chloro-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

20a (36 mg, 0.23 mmol) was dissolved in DMF (1.5 mL) with NaH (60% suspension, 9.6 mg, 0.24 mmol). 3a (75 mg, 0.24 mmol) was added slowly. The mixture was stirred at 90° C. for 8 h then cooled down to room temperature, diluted with ethyl acetate and washed with saturated NaHCO3. The organic layer was isolated, dried, filtered and evaporated. The residue was purified by preparative HPLC to afford 20-1, LCMS 432.1 (MH+). tR=5.21 (Method 5). EC50: 751 nM.

Provenance & Evidence