2-Fluoroethyl bromide → HCID 18705798, compound

Participants

Reaction Steps

Sodium hydride (0.05 g, 1.2 mmol) was washed with hexane under nitrogen and suspended in DMF (5 mL). 2-(Dipropylamino)-6-ethoxy-2,3-dihydro-1H-indene-5-carboxamide (81, 0.15 g, 0.5 mmol) in DMF (5 mL) was added dropwise at 0-5° C. over 30 min and the mixture stirred 30 min. 1-Bromo-2-fluoroethane (0.26 g, 2 mmol) in DMF (5 mL) was added and the resulting mixture was stirred 3 h. The reaction was quenched with saturated NaHCO3 and extracted with EtOAc. The organic layer is washed with water, brine, dried (MgSO4), filtered and concentrated to give crude product. Chromatographic purification yielded pure product 85 as an oil that was converted into the HCl salt and crystallized from EtOAc/hexane/MeOH to give a white solid (m.p. 158-159° C.).

Provenance & Evidence