Water → HCID 59299469, compound

Participants

Reaction Steps

Dissolve 3-(4-bromo-2-chlorobenzyl)-1-cyclohexylpyrrolidin-2-one (Example 55) (0.20 g, 0.54 mmol) in THF/NMP (10 mL/10 mL) under N2. Add Pd(dppf)Cl2 (0.04 g, 0.054 mmol) and cyclohexylzinc(II) bromide (1.08 mL, 0.5 M in THF) with stiring. Heat the reaction mixture to reflux for 4 hours until LC-MS shows the starting material has gone. Cool the reaction to room temperature and add water (20 mL). Extract the aqueous with EtOAc (3×50 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 10-50% of EtOAc-Hexane) to give 0.20 g (83%) of the title compound as a colorless oil: MS (APCI-pos mode) m/z (rel intensity) 374.3 (100), 376.3 (30).

Provenance & Evidence