Nitrogen → 5-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-2-ethenylpyridine

HRID 2183521노트

반응식

HRID 2183521 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[CH:4][N:3]=1.[CH:17]([Sn](CCCC)(CCCC)CCCC)=[CH2:18].N#N>O1CCOCC1.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>[Si:10]([O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH:17]=[CH2:18])=[N:3][CH:4]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

참가 물질

6

반응물 3

HCID 947NitrogenHCID 81998TributylvinyltinHCID 6425754Pyridine, 2-bromo-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

생성물 1

HCID 224732215-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-2-ethenylpyridine수율 84%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

A solution of 2-bromo-5-(tert-butyldimethylsilyloxymethyl)pyridine (1.0 g, 3.3 mmol) and vinyltributylstannane (2.09 g, 6.6 mmol) in 1,4-dioxane (30 ml) was degassed with a stream of N2 for 15 min and then Pd(PPh3)2Cl2 (116 mg, 5 mol %) was added and the reaction mixture heated at reflux under N2 for 20 h. After cooling to room temperature, the solvent were removed under reduced pressure and the mixture was azeotroped with xylene (2×10 ml). The residue was purified by column chromatography on silica using 20% EtOAc/iso-hexanes as eluent to yield the desired vinylpyridine (690 mg, 84%). 1H NMR (400 MHz, CDCl3) δ 8.40 (1H, s), 7.51 (1H, d, J=8.0 Hz), 7.21 (1H, d, J=8.0 Hz), 6.71 (1H, dd, J=17.5, 10.8 Hz), 6.06 (1H, d, J=17.5 Hz), 5.34 (1H, d, J=10.8 Hz), 4.64 (2H, s), 0.81 (9H, s), 0.00 (6H, s). m/z (ES+) 250 (M+H+).

후처리

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux under N2 for 20 h
  3. customthe solvent were removed under reduced pressure
  4. customthe mixture was azeotroped with xylene (2×10 ml)
  5. customThe residue was purified by column chromatography on silica using 20% EtOAc/iso-hexanes as eluent

출처 및 근거

ORD 기록
ord-125ce42d82604870b54f8b7f7dcf397d
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900209B2

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