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

HRID 594241ノート

反応式

HRID 594241 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e0ed0a106cb047a5beecfe728ba245f3
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

反応ノート

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