Dimethyl Sulfoxide → 2-((2,3-dihydrobenzo[1,4]dioxin-6-yl)methyl)-5-iodoisoquinolin-1(2H)-one

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Reaction Steps

5-Amino-2-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-2H-isoquinolin-1-one (260 mg, 0.00084 mol) was added to a solution of sodium nitrite (200 mg, 0.003 mol) in dimethyl sulfoxide (4 mL, 0.06 mol) at 35° C. Aqueous hydrogen iodide (0.5 mL, 0.004 mol) in dimethyl sulfoxide (4 mL, 0.06 mol) was added, and the reaction mixture was stirred for 1 hour. The cooled reaction mixture was neutralized with sat. aq. NaHCO3 and extracted with methylene chloride (3×50 mL). The combined methylene chloride extracts were washed with brine, dried over magnesium sulfate. The solvent was removed in vacuo and the residue was purified via flash column chromatography (12 g of silica gel, 0-50% EtOAc/Hexane) gave a light yellow solid. MS m/z (M+H) 420.0.

Provenance & Evidence