HCID 59226514, compound → HCID 59226570, compound

HRID 2046880Notes

Reaction equation

HRID 2046880 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH3:10])=[CH:4][C:3]=1[C:11]1[N:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][CH:12]=1>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH3:10])=[CH:4][C:3]=1[C:11]1[N:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 59226514HCID 59226514, compound

Product 1

HCID 59226570HCID 59226570, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-methyl 6-(2-fluoro-5-(prop-1-enyl)phenyl)-picolinate (1.0 equiv.) in MeOH (0.04 M) was 10% Pd/C (0.5 equiv.) and the reaction was placed under an atmosphere of hydrogen and left stirring overnight. The mixture was filtered over a pad of Celite and washed with MeOH. The filtrate was concentrated in vacuo to provide methyl 6-(2-fluoro-5-propylphenyl)picolinate as a light grey oil in 97% yield. LC/MS=274.2 (M+H), Rt=0.61 min.

Workup

  1. waitleft
  2. filtrationThe mixture was filtered over a pad of Celite
  3. washwashed with MeOH
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-45030ab449654ca09f1fde4a58455911
Source dataset
uspto-grants-2013_11
Patent number
US08592455B2

Reaction notes

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