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

HRID 715380Notes

Reaction equation

HRID 715380 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-edc721ad953a476b9ccb55c9527ebad3
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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