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

HRID 2183521ノート

反応式

HRID 2183521 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-125ce42d82604870b54f8b7f7dcf397d
出典データセット
uspto-grants-2005_05
特許番号
US06900209B2

反応ノート

読み込み中…