Methyl iodide → HCID 67179855, compound

Participants

Reaction Conditions

Reaction Steps

To (R,R)—N-[4-bromo-3-phenylisothiazol-5-yl]-2-methylcyclopropane-carboxamide (0.50 g, 1.48 mmol) in THF (3 mL), cooled to −78° C., is added 1.1 equivalent n-butyllithium (n-BuLi) (1.6M in hexane, 0.204 mL, 3.26 mmol). Internal temperature is maintained below −68° C. Following addition, the reaction mixture is allowed to stir for 1 h. 1.1 additional equivalents of n-BuLi (1.6M in hexane, 0.204 mL, 3.26 mmol) is then added while keeping the internal temperature below −66° C. After stirring for 2 h, the reaction mixture is warmed to −40° C. for 15 min; and then cooled back down to −78° C. Methyl iodide (0.10 mL, 1.63 mmol) is then added. The reaction mixture is allowed to warm to room temperature and stir over a weekend before the reaction is quenched with satd NH4Cl and diluted with EtOAc. The organic phase is washed with brine, dried (K2CO3) and evaporated. Chromatography over silica gel, eluting with 5-35% EtOAc in hexane, affords (R,R)-2-methyl-N-(4-methyl-3-phenylisothiazol-5-yl)-cyclopropanecarboxamide. Yield: 16.4%. ES-MS: 273.2 (m+1).

Provenance & Evidence