Iodine → HCID 67274065, compound

HRID 1020916Notes

Reaction equation

HRID 1020916 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([O:21][CH3:22])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(CCN(C)C)C.[Li+].CC([N-]C(C)C)C.[I:39]I>C1COCC1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([O:21][CH3:22])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[I:39])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 2724682Lithium diisopropylamideHCID 67273214HCID 67273214, compound

Product 1

HCID 67274065HCID 67274065, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  1. stirringstirred an additional 45 minutes at −20° C
  2. customThe reaction was then quenched with H2O
  3. concentrationconcentrated
  4. custompartitioned with EtOAc and 2N Na2CO3 solution
  5. washThe EtOAc layer was washed with H2O, aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-df3cc2bfe8c0493b985130593307c741
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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