9H-fluoren-9-ylmethyl N-[(2S)-1-chloro-3-methyl-1-oxobutan-2-yl]carbamate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-(9H-fluoren-9-yl)methyl 1-chloro-3-methyl-1-oxobutan-2-ylcarbamate (0.11 g, 307 μmol, Eq: 3.1) was added to a solution of N-(2,6-difluorophenyl)-3,3-dimethylindoline-2-carboxamide (30 mg, 99.2 μmol, Eq: 1.00) and pyridine (40 μL, 496 μmol, Eq: 5) in DCM (1 mL) and the resulting solution was stirred at rt for 3 h. The reaction mixture was diluted with EtOAc (20 mL) and washed with 1 M aqueous HCl (10 mL), 1 M aqueous NaOH (10 mL) and brine (10 mL), dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 4 g, 0% to 30% EtOAc in hexanes) to give (S)-(9H-fluoren-9-yl)methyl 1-(2-(2,6-difluorophenylcarbamoyl)-3,3-dimethylindolin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate as a viscous oil (71 mg). washed with 1 M aqueous HCl (10 mL), 1 M aqueous NaOH (10 mL) and brine (10 mL) dried over Na2SO4 concentrated in vacuo The crude material was purified by flash chromatography (silica gel, 4 g, 0% to 30% EtOAc in hexanes)