2-(1-Azidoethyl)-5-fluoropyridine → 1-(5-Fluoropyridin-2-YL)ethanamine

HRID 1641397Notes

Reaction equation

HRID 1641397 reaction equation
[N:1]([CH:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][N:7]=1)[CH3:5])=[N+]=[N-]>CO.[Pd]>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:4]([NH2:1])[CH3:5])=[N:7][CH:8]=1

Participants

4

Reactant 1

HCID 866248112-(1-Azidoethyl)-5-fluoropyridine

Product 1

HCID 574158241-(5-Fluoropyridin-2-YL)ethanamineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-(1-Azidoethyl)-5-fluoropyridine (Method 3; 7.7 g, 46.3 mmol) and Pd (10 wt. %, dry basis, on activated carbon, 2.47 g, 2.32 mmol) in methanol (20 ml) was placed under H2 for 4 hours. The reaction was then evacuated, flushed with N2, filtered, washed with MeOH (3×30 ml), and concentrated to give the title compound as pale yellow oil (6.40 g, 99%). 1H NMR (400 MHz) 8.45 (d, J=2.8 Hz, 1H), 7.67 (ddd, J=2.8, 2.8 and 2.8 Hz, 1H), 7.54 (m, 1H), 4.01 (q, J=6.8 Hz, 1H), 1.97 (b, 2H), 1.27 (d, J=6.8 Hz, 3H).

Workup

  1. customThe reaction was then evacuated
  2. customflushed with N2
  3. filtrationfiltered
  4. washwashed with MeOH (3×30 ml)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fb702058d6c542f9911267a5f8d61d76
Source dataset
uspto-grants-2012_02
Patent number
US08114989B2

Reaction notes

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