2,2,6,6-Tetramethylpiperidine → HCID 18379028, compound

Participants

Reaction Conditions

Reaction Steps

2,2,6,6-tetramethylpiperdine (4.5 mL, 26.5 mMol) was dissolved in a solution of anhydrous THF (100 mL) and anhydrous 1,2-dimethoxyethane (50 mL) under an atmosphere of dry N2 and the solution was then cooled to −78° C. To this solution was added 2.5 M n-butyllithium in hexanes (9.6 mL, 24.1 mMol) and the mixture was stirred for 20 minutes. To this solution was added 1-methyl-2-phenylthio-1-H-imidazole (4.58 g, 24.1 mMol) and the solution was stirred at −78° C. for 45 minutes. 6-(4-Chloro-benzoyl)-1-methyl-4-(3-vinyl-phenyl)-1H-quinolin-2-one (9.64 g, 24.1 mMol) was then added and the solution was slowly warmed to ambient temperature and stirred overnight. The reaction was quenched with saturated aqueous NH4Cl and the solution was partitioned between water and EtOAc. The aqueous layer was washed 2 more times with EtOAc. The EtOAc extracts were combined and dried over Na2SO4, filtered and concentrated under vacuum to give a yellow oil. The oil was chromatographed on flash silica gel eluting with a gradient from EtOAc/hexanes (1:1) to EtOAc/hexanes (4:1) to give 8.66 g of the titled compound as a foam.

Provenance & Evidence