1-Piperidinecarboxaldehyde → (2,2'-Bipyridine)-6-carbaldehyde

HRID 594241노트

반응식

HRID 594241 반응식
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][CH:3]=1.[Li]CCCC.N1([CH:25]=[O:26])CCCCC1.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[N:7]1[C:2]([CH:25]=[O:26])=[CH:3][CH:4]=[CH:5][C:6]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

참가 물질

7

반응물 4

HCID 174291-PiperidinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 117911522-Bromo-6-(pyridin-2-yl)pyridineHCID 178418339Butyllithium

생성물 1

HCID 11095276(2,2'-Bipyridine)-6-carbaldehyde

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

A cooled (−78° C.) solution of commercially available 6-bromo-2,2′-bipyridine (600 mg; 2.55 mmol) in anh. THF (10 ml) was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.60 ml; 2.56 mmol), and the resulting mixture was further stirred at −78° C., under nitrogen, for 30 min. Piperidine-1-carbaldehyde (577 mg; 5.10 mmol) was added dropwise to the cooled (−78° C.) reaction mixture, and stirring was continued at −78° C. for 30 min. Aq. sat. NH4Cl (25 ml) and AcOEt (50 ml) were added, and the separated organic layer was further washed with brine (20 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (toluene/AcOEt=8/2) afforded [2,2′-bipyridine]-6-carbaldehyde as a dark-purple solid. LC-MS (conditions C): tR=0.75 min.; [M+H]+: 185.24 g/mol.

후처리

  1. temperaturecooled
  2. custom(−78° C.) reaction mixture
  3. stirringstirring
  4. waitwas continued at −78° C. for 30 min
  5. washthe separated organic layer was further washed with brine (20 ml)
  6. dry with materialdried over anh. MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure
  9. customPurification by FC (toluene/AcOEt=8/2)

출처 및 근거

ORD 기록
ord-e0ed0a106cb047a5beecfe728ba245f3
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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