N-(1-(5-Fluoropyridin-2-yl)vinyl)acetamide → Acetamide, N-[(1S)-1-(5-fluoro-2-pyridinyl)ethyl]-

HRID 926710Notes

Reaction equation

HRID 926710 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][C:11](=[O:13])[CH3:12])=[CH2:9])=[N:6][CH:7]=1>CCO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 66736029N-(1-(5-Fluoropyridin-2-yl)vinyl)acetamide

Product 1

HCID 66735551Acetamide, N-[(1S)-1-(5-fluoro-2-pyridinyl)ethyl]-Yield 103,535.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
27.5 °C

Procedure

10% Pd/C (100 mg) was added to a solution of N-(1-(5-fluoropyridin-2-yl)vinyl)acetamide (440 g, 2.2 mmol) in EtOH (10 mL) and the mixture was stirred continuously under hydrogen atmosphere at 20-35° C. for 1.5 h. The reaction mixture was filtered over a celite bed- and the filtrate was concentrated under reduced pressure to afford 415 g of the title compound as a yellowish brown liquid. MS (ESI): m/z 183 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered over a celite bed-
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c10916ed3f3c486b97d2eed9a1cb6e10
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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