Iodine → HCID 86651927, compound

Participants

Reaction Steps

To a solution of 2-(2,4-dimethoxybenzyl)-5-(2,4-dimethoxybenzylamino)-6-nitroisoindoline-1,3-dione T-02 (6.1 g, 12 mmol) in anhydrous tetrahydrofuran (50 mL) cooled in an ice bath was added borane dimethyl sulfide complex (10 M, 36 mL, 360 mmol) in a dropwise manner. The reaction mixture was heated under reflux for 4 hours. The reaction mixture was cooled in an ice bath and methanol (75 mL) was added in a dropwise manner. To the reaction mixture were added triethylamine (6 mL), acetic acid (9 mL) and a solution of iodine (1 g) in anhydrous tetrahydrofuran (5 mL). The reaction mixture was stirred at room temperature overnight. Solvent was removed under reduced pressure. The crude product was diluted with ethyl acetate. The organic layer was washed with 1 N sodium hydroxide solution, water and saturated brine. The organic layer was dried over sodium sulfate. Solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography to afford the desired N,2-bis(2,4-dimethoxybenzyl)-6-nitroisoindolin-5-amine T-03 (2.7 g, 5.6 mmol).

Provenance & Evidence