2-(Azidomethyl)-6-(2,2,2-trifluoroethoxy)pyridine → [6-(2,2,2-Trifluoroethoxy)pyridin-2-yl]methanamine

HRID 623432ノート

反応式

HRID 623432 の反応式
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[N:6]=1)=[N+]=[N-]>CO.[Pd]>[F:16][C:13]([F:14])([F:15])[CH2:12][O:11][C:7]1[N:6]=[C:5]([CH2:4][NH2:1])[CH:10]=[CH:9][CH:8]=1

参加物

4

反応物 1

HCID 1317340902-(Azidomethyl)-6-(2,2,2-trifluoroethoxy)pyridine

生成物 1

HCID 62290450[6-(2,2,2-Trifluoroethoxy)pyridin-2-yl]methanamine収率 68.9%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A mixture of 2-(azidomethyl)-6-(2,2,2-trifluoroethoxy)pyridine (Step-5, 0.44 g, 1.90 mmol) and palladium 10% on carbon (0.070 g) in methanol (12 mL) is vigorously stirred at room temperature under hydrogen atmosphere (0.3 MPa) for 3 hours. After filtration through a pad of celite, the filtrate is concentrated in vacuo. The residue is diluted with methanol (4 mL) and applied onto a strong cation exchange cartridge (BondElute(registered trademark) SCX, 1 g/6 mL, Varian Inc.), and the solid phase matrix is rinsed with methanol (5 mL). The crude mixture is eluted with 1M ammonia in methanol (5 mL) and concentrated under reduced pressure to give 0.27 g (68% yield) of the title compound as dark brown oil.

後処理

  1. filtrationAfter filtration through a pad of celite
  2. concentrationthe filtrate is concentrated in vacuo
  3. additionThe residue is diluted with methanol (4 mL)
  4. wash), and the solid phase matrix is rinsed with methanol (5 mL)
  5. washThe crude mixture is eluted with 1M ammonia in methanol (5 mL)
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-07981e7ad62744beb74279f370a3a641
出典データセット
uspto-grants-2016_04
特許番号
US09302991B2

反応ノート

読み込み中…