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

HRID 623432노트

반응식

HRID 623432 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-07981e7ad62744beb74279f370a3a641
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302991B2

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