HCID 22612145, compound → HCID 22612333, compound

HRID 844075Notes

Reaction equation

HRID 844075 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[C:12](/[CH:13]=[CH:14]/[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[C:12]([CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 22612145HCID 22612145, compound

Product 1

HCID 22612333HCID 22612333, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 60 mg (0.18 mmol) (E)-2-(4-Fluorophenoxy)-3-[3-(4-methoxyphenyl)-1-propenyl]-pyridine in 50 mL of ethanol was added 50 mg of 10%Pd/C, and the mixture was hydrogenated at 45 psi on a Parr Shaker Apparatus for 2 h. The catalyst was removed by filtration, and the filtrate was concentrated to afford 50 mg (83% yield) of the title compound as a colorless oil. 1H NMR (CDCl3) d 1.92-2.06 (2H, m), 2.67 (2H, t, J=8 Hz), 2.75 (2H, t, J=8 Hz), 3.80 (3H, s), 6.82-7.14 (9H, m), 7.52 (1H, dd, J=2, 7 Hz), 7.99 (1H, dd, J=2, 5 Hz); thermospray MS: m/e 338 (M++1).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c026c0a37c094f17bceb93117532a2d8
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

Loading…