Methyl 4-amino-5-fluoro-3-methoxy-6-vinylpicolinate → HCID 71150525, compound

HRID 407230Notes

Reaction equation

HRID 407230 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([CH:9]=[CH2:10])[N:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:3]=1[O:15][CH3:16]>CCOC(C)=O.[Pd]>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][CH3:10])[N:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:3]=1[O:15][CH3:16]

Participants

4

Reactant 1

HCID 86675408Methyl 4-amino-5-fluoro-3-methoxy-6-vinylpicolinate

Product 1

HCID 71150525HCID 71150525, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To methyl 4-amino-5-fluoro-3-methoxy-6-vinylpicolinate (0.32 g, 1.42 mmol) in EtOAc (5 mL) was added 10% palladium on carbon (Pd/C, 0.16 g, 0.15 mmol). The mixture was stirred under an atmosphere of hydrogen overnight, filtered through Celite and concentrated to provide methyl 4-amino-6-ethyl-5-fluoro-3-methoxypicolinate (0.21 g, 0.92 mmol) as a white solid: mp 110.5-113.0° C.; 1H NMR (400 MHz, CDCl3) δ 4.41 (s, 2H), 3.96 (s, 3H), 3.90 (s, 3H), 2.81 (qd, J=7.6, 2.7 Hz, 2H), 1.26 (t, J=7.6 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 165.2, 148.6, 146.2, 144.2, 136.8, 136.1, 61.5, 52.7, 25.3, 12.9; 19F NMR (376 MHz, CDCl3) δ −142.6; EIMS m/z 228.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b947fab1c7a9431c8b6b420fe7df8fd8
Source dataset
uspto-grants-2014_06
Patent number
US08754229B2

Reaction notes

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