2,6-Dibromopyridine → 2-Bromo-6-cyclopentylpyridine

HRID 1796020ノート

反応式

HRID 1796020 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[Br-].[CH:10]1([Zn+])[CH2:14][CH2:13][CH2:12][CH2:11]1>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:3]=1

参加物

5

反応物 2

HCID 122742,6-DibromopyridineHCID 178419768HCID 178419768、化合物

生成物 1

HCID 221807702-Bromo-6-cyclopentylpyridine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

実験手順

To 2,6-dibromopyridine (5.9 g, 25 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmol) was added cyclopentylzinc bromide (50 ml, 0.5 M solution in tetrahydrofuran) and the mixture heated at reflux for 18 h. The reaction was diluted with ethyl acetate and washed with water. The organic phase was separated, dried over magnesium sulfate, filtered and evaporated in vacuo to give an oil. The crude product was chromatographed on silica, eluting on a gradient from 1 to 5% methanol in dichloromethane, to give 2-bromo-6-cyclopentylpyridine (3.25 g) as a white solid: δH (400 MHz, CDCl3) 1.60-1.90 (6H, m), 2.09 (2H, m), 3.17 (1H, m), 7.12 (1H, d, J 7.4), 7.28 (1H, d, J 7.4), 7.44 (1H, t, J 7.2); m/z (ES+) 226:228 (1:1) (M++H).

後処理

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 h
  3. washwashed with water
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give an oil
  9. customThe crude product was chromatographed on silica
  10. washeluting on a gradient from 1 to 5% methanol in dichloromethane

出典と根拠

ORDレコード
ord-a25407265d444a9bb3742ca2e2d2d71a
出典データセット
uspto-grants-2006_04
特許番号
US07030128B2

反応ノート

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