Iodine → HCID 67274065, 화합물

HRID 1020916노트

반응식

HRID 1020916 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 67274065HCID 67274065, 화합물수율 98.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-df3cc2bfe8c0493b985130593307c741
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716493B2

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