Sodium hydride → HCID 89783551, compound

Participants

Reaction Steps

(S)-tert-Butyl 3-hydroxypiperidine-1-carboxylate (Astatech Inc., Bristol, Pa.; 406 mg, 2.02 mmol) was added to a suspension of NaH (81 mg, 2.02 mmol) in THF (2.5 mL) and the resulting suspension 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; 75 mg, 0.25 mmol) was then added and the resulting suspension was stirred at RT for 5 min, then heated at 70° C. for 1.25 h. The mixture was cooled to RT and partitioned between EtOAc (60 mL) and saturated aq. NH4Cl (20 mL). The organic layer was separated, sequentially washed with water (20 mL) then brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo to give (S)-tert-butyl 3-((8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinolin-2-yl)oxy)piperidine-1-carboxylate as a light yellow solid: m/z (ESI, +ve ion) 463.1 (M+H)+. The material was used in the subsequent step without further purification.

Provenance & Evidence