Acetic Acid → HCID 178482798, compound

Participants

Reaction Steps

An amount of 300 mg (0.51 mmol) of (4Z)-4-[({4-amino-3-[(triisopropylsilyl)oxy]benzyl}amino)methylene]-6-iodoisoquinoline-1,3(2H,4H)-dione and formylaldehyde (45.9 mg, 1.53 mmol) were dissolved in tetrahydrofuran (3 mL) and methanol (2 mL). After stirring for ten minutes, a mixture of sodium cyanoborohydride (64.1 mg, 1.02 mmol) and acetic acid (0.4 mL, 5.1 mmol) were added drop-wise. The mixture is allowed to stir for 2.5 hours. Tetrabutylammonium fluoride (2 mL) is added and stirred for additional 1 hour. The mixture is neutralized with 1 NHCl solution and extracted with dichloromethane (200 ml), dried over sodium sulfate and evaporated. The desired final product is purified by column chromatography to afford 60 mg (26% yield) of a light brown solid.; mp 198-199° C.

Provenance & Evidence