Sodium Iodide → HCID 88296093, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 61 mg (0.160 mmol) of rac-4'-(hydroxymethyl)-3',6'-dihydroxyspiro[isobenzofuran-1(3H), 9'-[9H]xanthen]-3-one (2), 125 mg (0.33 mmole) of (S)-2,2,2-trifluoro-N-[1-methyl-2-[4-(1-piperazinylsulfonyl)phenyl]ethyl]acetamide (17), 150 mg (1.0 mmol) of sodium iodide and 600 μL (5.15 mmol) of 2,6 lutidine in 4.5 mL of anhydrous dimethylformamide was heated at 120° C. for 2 hours. The reaction mixture was concentrated and 20 mL of a 1:1 mixture of methanol:THF was added. Inorganic salt was filtered off and the filtrate was concentrated. The residue was purified by thin layer chromatography using 50% chloroform in ethyl acetate to yield 41 mg of (S)-N-[2-[4-[[4-[(3',6'-dihydroxy-3-oxospiro[isobenzo-furan-1(3H),9'-[9H]xanthen]-4'-yl)methyl]-1-piperazinyl]-sulfonyl]phenyl]-1-methylethyl]-2,2,2-trifluoroacetamide (1:1 epimers) (18) (0.056 mmol, 35%) as an orange red powder. NMR, IR and MS data confirmed the compound identity.

Provenance & Evidence