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Tert-butyl 2-iodobenzoate → t-Butyl 2-[4-[(2-ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-yl)methyl]phenyl]benzoate

HRID 1655526
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HRID 1655526 반응식
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][N:6]2[C:13]=1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Sn](C)(C)C)=[CH:17][CH:16]=1)[CH3:2].I[C:26]1[CH:38]=[CH:37][CH:36]=[CH:35][C:27]=1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][N:6]2[C:13]=1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:26][C:27]=2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:17][CH:16]=1)[CH3:2]
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참가 물질

5

반응물 2

HCID 11438134Tert-butyl 2-iodobenzoateHCID 197841424-[(2-Ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-yl)methyl]phenyltrimethylstannane

생성물 1

HCID 19784151t-Butyl 2-[4-[(2-ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-yl)methyl]phenyl]benzoate수율 73%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매
HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

To a solution of 0.149 g (0.35 mmol) of the product of Step G and 0.132 g (0.43 mmol) of t-butyl 2-iodobenzoate in 1 mL of anhydrous DMF was added 5 mg of bis(triphenylphosphine)palladium(II) chloride. The mixture was degassed, flushed with nitrogen, then magnetically stirred under a nitrogen atmosphere for 12 hours at 100° C. The reaction mixture was cooled to room temperature, then partitioned between EtOAc and water. The organic layer was extracted, separated, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 50% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded 0.111 g (73%) of the title compound as an off-white amorphous solid.

후처리

  1. customThe mixture was degassed
  2. customflushed with nitrogen
  3. temperatureThe reaction mixture was cooled to room temperature
  4. custompartitioned between EtOAc and water
  5. extractionThe organic layer was extracted
  6. customseparated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified on a silica gel flash chromatography column
  11. washeluted with 50% EtOAc-hexane
  12. customEvaporation of the purified fractions
  13. customdrying in vacuo

출처 및 근거

ORD 기록
ord-904b5b14ddf64470a58787b61e8a0253
출처 데이터셋
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05250521

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