Sodium hydride → HCID 89793619, compound

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Reaction Steps

Similar to the method described in Example 103, tert-butyl 4-hydroxypiperidine-1-carboxylate (Aldrich; 357 mg, 1.77 mmol) was added to a suspension of NaH (70.9 mg, 1.77 mmol) in DMF (2.0 mL) and the resulting light yellow solution was stirred at RT for 10 min. 2-(2-Chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 66 mg, 0.22 mmol) was added and the resulting dark red solution was stirred at RT for 5 min, then heated at 70° C. for 2.5 h. The mixture was cooled to RT and partitioned between EtOAc (100 mL) and saturated aq. NH4Cl (50 mL). The organic layer was separated, sequentially washed with water (40 mL) and brine (40 mL), and then dried over MgSO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-10% MeOH in DCM) gave tert-butyl 4-((8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinolin-2-yl)oxy)piperidine-1-carboxylate as an orange oil. m/z (ESI, +ve ion) 463.3 (M+H)+.

Provenance & Evidence