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

HRID 715380ノート

反応式

HRID 715380 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 (0.44 g, 1.90 mmol, Step-5) and palladium 10% on carbon (0.070 g) in methanol (12 mL) is vigorously stirred at rt 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™ 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. washthe 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-edc721ad953a476b9ccb55c9527ebad3
出典データセット
uspto-grants-2015_11
特許番号
US09187475B2

反応ノート

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