5-Ethenyl-6-fluoropyridin-3-amine → 5-Ethyl-6-fluoropyridin-3-amine

HRID 2185767Notes

Reaction equation

HRID 2185767 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH2:10])[C:5]([F:8])=[N:6][CH:7]=1>CO.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][CH3:10])[C:5]([F:8])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 184589355-Ethenyl-6-fluoropyridin-3-amine

Product 1

HCID 224515375-Ethyl-6-fluoropyridin-3-amineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of the 5-amino-2-fluoro-3-vinylpyridine from Step 126c above (2.30 g, 16.6 mmol) in MeOH (50 mL) was added to a suspension of 10% palladium on activated carbon (Aldrich, 0.10 g) in MeOH (75 mL). The mixture was placed under an atmosphere of H2 (balloon) for 48 h. The catalyst was removed by filtration and the solvent was evaporated to yield the title compound as a beige solid (2.31 g, 99%): 1H NMR (CDCl3, 300 MHz) δ1.22 (t, J=7.5 Hz, 3H), 2.58 (q, J=7.5 Hz, 2H), 6.96 (dd, J=3.0, 5.1 Hz, 1H), 7.45 (m, 1H); MS (CI/NH3) m/z 141 (M+H)+, 158 (M+NH4)+.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7620843a85a04db9bce817f01f03e15b
Source dataset
uspto-grants-2002_06
Patent number
US06403575B1

Reaction notes

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