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

HRID 715380노트

반응식

HRID 715380 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 (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.

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. 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

출처 및 근거

ORD 기록
ord-edc721ad953a476b9ccb55c9527ebad3
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187475B2

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