Benzylamine → HCID 90047497, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-5-fluoro-1,3,3-trimethylindolin-2-one (2.8 g, 10.3 mmol) in tetrahydrofuran (280 ml) under an argon atmosphere were added 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (320 mg, 514 μmol), tris(dibenzylideneacetone)dipalladium(0) (471 mg, 514 μmol), benzylamine (2.21 g, 2.25 ml, 20.6 mmol) and a 1 M solution of lithium bis(trimethylsilyl)amide (25.7 ml, 25.7 mmol). The reaction mixture was heated to 80° C. in the microwave for 45 minutes and then diluted with ethyl acetate, water and 2 N aqueous Na2CO3 solution. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate. The solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/heptane as eluent. The title compound was obtained as light yellow powder (1.57 g).

Provenance & Evidence