2,6-Lutidine → 5,7-Difluoroquinoline-6-carbaldehyde

HRID 69137ノート

反応式

HRID 69137 の反応式
[F:1][C:2]1[C:11]([CH:12]=C)=[C:10]([F:14])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:24].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[C:11]([CH:12]=[O:24])=[C:10]([F:14])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

参加物

7

反応物 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 579173805,7-Difluoro-6-vinyl-quinoline

生成物 1

HCID 579172825,7-Difluoroquinoline-6-carbaldehyde

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

5,7-Difluoro-6-vinyl-quinoline (iv) (614 mg, 3.21 mmol) was dissolved in dioxane (1.7 mL) and water (0.6 mL). 2,6-lutidine (0.761 mL, 6.42 mmol), sodium periodate (2.75 g, 12.85 mmol) and osmium tetroxide (653 mg, 0.064 mmol) were added to the previous solution. The RM was stirred at rt for 15 min. A precipitate was formed. Water was added to the RM and it was extracted twice with EtOAc. The organics were joined and washed with brine, dried over Na2SO4 and the solvent was removed. The residue was purified by MPLC with Hexane and EtOAc to give the title compound as a white solid (tR 1.2 min (conditions 2), MH+=244, 1H-NMR in DMSO-d6: 10.36 (s, 1H); 9.15 (s, 1H); 8.65 (d, 1H); 7.79 (d, 1H); 7.69 (dd, 1H)).

後処理

  1. customA precipitate was formed
  2. extractionwas extracted twice with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed
  6. customThe residue was purified by MPLC with Hexane and EtOAc

出典と根拠

ORDレコード
ord-f4c19fafe01e46b9b818cb859af5ec65
出典データセット
uspto-grants-2014_09
特許番号
US08822468B2

反応ノート

読み込み中…