2-Mercaptoethanol → HCID 9967203, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (Z)-5-fluoro-4-[1-iodo-3-oxo-3-(1H-pyrrol-2-yl)-propenyl]-1,3-dihydro-indol-2-one (from Example 8 above) (300 mg, 0.60 mmol) and neat 2-mercaptoethanol (Sigma, 4 mL) was treated with NaH (Aldrich, 98%, 210 mg that was emulsified with 0.4 mL of mineral oil) in small portions at room temperature. After the evolution of gas stopped, the mixture was heated gradually to 120° C. and stirred at this temperature for 6 hours. The reaction mixture was then poured in a mixture of ethyl acetate and water. The aqueous layer was extracted few more times with ethyl acetate and the combined organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by HPLC (silica gel, with 25% ethyl acetate in hexanes) and then precipitated out of THF with excess pentane to give 6-fluoro-5-(2-hydroxy-ethylsulfanyl)-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one as a yellow solid. (Yield 98 mg, 49%).

Provenance & Evidence