2-(Tributylstannyl)pyridine → 4-(3-Bromo-furan-2-yl)-pyridine

HRID 1593422ノート

反応式

HRID 1593422 の反応式
C([Sn]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)(CCCC)CCCC)CCC.Br[C:21]1[O:22][CH:23]=[CH:24][C:25]=1[Br:26]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Br:26][C:25]1[CH:24]=[CH:23][O:22][C:21]=1[C:18]1[CH:19]=[CH:14][N:15]=[CH:16][CH:17]=1

参加物

6

反応物 2

HCID 6077842-(Tributylstannyl)pyridineHCID 70215012,3-Dibromofuran

生成物 1

HCID 157218314-(3-Bromo-furan-2-yl)-pyridine収率 25%

試薬・触媒・溶媒 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A solution of tributylstannylpyridine (8.0 g, 21.7 mmol) and 2,3-dibromofuran (5.9 g, 26.1 mmol) in dry toluene (200 ml) was treated with bis(triphenylphosphine)palladium (II) chloride (1.5 g, 2.2 mmol) and heated at 100° C. overnight. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate to afford the title compound (1.2 g, 25%); 1H NMR (CDCl3) 8.66 (2H, d, J 11 Hz), 7.84 (2H, d, J 11 Hz), 7.50 (1H, d, J 3 Hz), 6.60 (1H, d, J 3 Hz).

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with ethyl acetate

出典と根拠

ORDレコード
ord-de1c0fa68a7a4d31b1479e821a53b612
出典データセット
uspto-grants-2007_11
特許番号
US07297694B2

反応ノート

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