Chlorosuccinimide → HCID 53242051, compound

Participants

Reaction Conditions

Reaction Steps

2.63 g (8.26 mmol) of tert-butyl N-{5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}carbamate are dissolved in 100 ml of dry THF in a dried Schlenk flask under nitrogen and cooled to −78° C. 11 ml of a 15% solution of n-BuLi in n-hexane are then slowly added dropwise, and the mixture is stirred at −78° C. for 20 min. 1120 mg (8.38 mmol) of N-chlorosuccinimide dissolved in 1 ml of dry THF are subsequently added dropwise, and the mixture is stirred at −78° C. for 15 min, then quenched using 10 ml of n-butanol and warmed to RT. The solvent is removed in vacuo, and the residue is purified directly by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 99/1), giving 2.3 g (6.51 mmol, 78%) of tert-butyl N-{2-chloro-5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}-carbamate as beige solid from PE; ESI-MS: m/e: 353 ([M+H]+).

Provenance & Evidence