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

HRID 1796020노트

반응식

HRID 1796020 반응식
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

참가 물질

5

반응물 2

HCID 122742,6-DibromopyridineHCID 178419768HCID 178419768, 화합물

생성물 1

HCID 221807702-Bromo-6-cyclopentylpyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a25407265d444a9bb3742ca2e2d2d71a
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030128B2

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