Iodine → HCID 67274065, compound

Participants

Reaction Steps

To 541 mg (1.71 mmol) of the protected indole from step 1 in 20 mL dry THF at −20° C. was added 269 μL (1.8 mmol, 1.05 eq) TMEDA, then LDA (1.1 mL, 2.22 mmol, 1.3 eq) dropwise. The reaction was stirred for 45 minutes and iodine (879 mg, 3.42 mmol, 2 eq) in 4 mL THF was added slowly, and stirred an additional 45 minutes at −20° C. The reaction was then quenched with H2O, concentrated and partitioned with EtOAc and 2N Na2CO3 solution. The EtOAc layer was washed with H2O, aqueous NaCl, dried (MgSO4), and concentrated under vacuum to yield 750 mg of 1-benzenesulfonyl-2-iodo-4,5-dimethoxy-1H-indole.

Provenance & Evidence