Sodium Iodide → HCID 58591563, compound

Participants

Reaction Steps

A mixture of NaI (24 mg, 0.16 mmol)) and TMSCl (20 uL, 0.16 mmol) in acetonitrile (0.5 mL) was stirred for 15 min at room temperature. A solution of 1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-1-thiazol-5-yl-ethanol (Compound 17-1) (3 mg, 0.01 mmol) in dichloromethane (1.3 mL) was added and the reaction was stirred in a sealed vial at 100° C. for 3 hrs. The mixture was quenched with 1M Na2S2O3 until colorless and diluted NH4OH was added until pH ˜8. The product was extracted with EtOAc and the combined organic layers were washed with diluted NH4OH, concentrated and subjected to mass triggered preparative HPLC purification to afford dimethyl-{2-[3-(1-thiazol-5-yl-ethyl)-benzo[b]thiophen-2-yl]-ethyl}-amine (Compound 17-2). MH+=317.0, tR=4.24 min, (Method 2).

Provenance & Evidence