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1,4-Dioxane → 5-cyclopropyl-1H-pyrrolo[2,3-b]pyridine

HRID 509932
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HRID 509932 반응식
I[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[Br-].[CH:12]1([Zn+])[CH2:14][CH2:13]1.O1CCOCC1>Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1.CO>[CH:12]1([C:2]2[CH:3]=[C:4]3[CH:10]=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)[CH2:14][CH2:13]1
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참가 물질

6

반응물 3

HCID 312751,4-DioxaneHCID 242292145-Iodo-1H-pyrrolo[2,3-b]pyridineHCID 178419765HCID 178419765, 화합물

생성물 1

HCID 582589265-cyclopropyl-1H-pyrrolo[2,3-b]pyridine

시약·촉매·용매 2

HCID 178418745HCID 178418745, 화합물촉매HCID 887Methanol용매

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온도
100 °C

실험 절차

5-Iodo-1H-pyrrolo[2,3-b]pyridine (21, 0.343 g, 1.40 mmol), cyclopropylzinc bromide (22, 12.6 mL, 0.500 M in tetrahydrofuran, 6.32 mmol) and [1,3-bis(diphenylphosphino)propane]-nickel(II) chloride (76.2 mg, 0.14 mmol) and 5.37 mL of 1,4-dioxane were combined in a reaction vessel. The reaction was heated at 100° C. overnight, then methanol was added and the reaction was concentrated under vacuum. Ethyl acetate and water were added to the residue, then filtered through a bed of celite and the celite bed washed with ethyl acetate. The filtrate was separated and the aqueous layer extracted with ethyl acetate. The organic layers were combined and washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with ethyl acetate and hexane. Appropriate fraction were combined and concentrated under vacuum to provide the desired compound. MS (ESI) [M+H+]+=159.0.

후처리

  1. concentrationthe reaction was concentrated under vacuum
  2. additionEthyl acetate and water were added to the residue
  3. filtrationfiltered through a bed of celite
  4. washthe celite bed washed with ethyl acetate
  5. customThe filtrate was separated
  6. extractionthe aqueous layer extracted with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under vacuum
  11. customThe resulting material was purified by silica gel column chromatography
  12. washeluting with ethyl acetate and hexane
  13. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-763005697d17419b9823e16e3de7306a
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096593B2

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