(E)-Methyl 2-(4-fluorostyryl)isonicotinate → Methyl 2-(4-fluorophenethyl)isonicotinate

HRID 1963258Notes

Reaction equation

HRID 1963258 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5](/[CH:6]=[CH:7]/[C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66732050(E)-Methyl 2-(4-fluorostyryl)isonicotinate

Product 1

HCID 66731796Methyl 2-(4-fluorophenethyl)isonicotinateYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(E)-methyl 2-(4-fluorostyryl)isonicotinate (3.6 g, 13.99 mmol) was dissolved in methanol (200 mL). Palladium on charcoal (0.149 g, 1.40 mmol) was added and the mixture was hydrogenated at atmospheric pressure and room temperature for 18 h. The catalyst was filtered off and the filtrate was evaporated. Methyl 2-(4-fluorophenethyl)isonicotinate (3.63 g, 99%) was isolated. MS m/z 260 (M+H)+

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-c5aca35cd6ee4c5bb7f054ea2429835a
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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