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Iodine → 5-(3,4-Dimethoxy-phenyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine

HRID 1820904
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HRID 1820904 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[C:13]3[CH:19]=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[I:20]I.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[C:13]3[C:19]([I:20])=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 807IodineHCID 61475Sodium Thiosulfate PentahydrateHCID 101492305-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 598121695-(3,4-Dimethoxy-phenyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran
용매
2회

반응 조건

온도
-40 °C

실험 절차

5-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine, 82, (0.270 g, 0.00106 mol) was dissolved in Tetrahydrofuran (8.5 mL, 0.10 mol) under an atmosphere of Nitrogen. The solution was stirred at −40° C. and Iodine (0.269 g, 0.00106 mol) dissolved in 2.5 mL of Tetrahydrofuran was added. The chilled reaction mixture was stirred for 2 h and was then quenched with the addition of Sodium thiosulfate, pentahydrate (0.13 g, 0.00053 mol) in water (1M). The reaction mixture was partitioned between water (20 mL and ethyl acetate (30 mL). The two layers were seperated, and the aquous layer was extracted with ethyl acetate. The organic layers were washed with water and brine, dried with sodium sulfate, then concentrated under reduced pressure. The dark colored crude residue was carried onto the next reaction without further purification.

후처리

  1. additionwas added
  2. customThe chilled reaction mixture
  3. stirringwas stirred for 2 h
  4. customThe reaction mixture was partitioned between water (20 mL and ethyl acetate (30 mL)
  5. customThe two layers were seperated
  6. extractionthe aquous layer was extracted with ethyl acetate
  7. washThe organic layers were washed with water and brine
  8. dry with materialdried with sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe dark colored crude residue was carried onto the next reaction without further purification

출처 및 근거

ORD 기록
ord-7b79f6b007bb4427876698b4723b5ba2
출처 데이터셋
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07605168B2

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