Methyl 6-(3-(benzyloxy)-2,6-difluorophenyl)-5-fluoropicolinate → HCID 59226549, compound

HRID 1523518Notes

Reaction equation

HRID 1523518 reaction equation
C([O:8][C:9]1[C:10]([F:27])=[C:11]([C:16]2[N:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][C:17]=2[F:26])[C:12]([F:15])=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[F:27][C:10]1[C:9]([OH:8])=[CH:14][CH:13]=[C:12]([F:15])[C:11]=1[C:16]1[N:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][C:17]=1[F:26]

Participants

5

Reactant 1

HCID 59226393Methyl 6-(3-(benzyloxy)-2,6-difluorophenyl)-5-fluoropicolinate

Product 1

HCID 59226549HCID 59226549, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 6-(3-(benzyloxy)-2,6-difluorophenyl)-5-fluoropicolinate (1.0 equiv.) in methanol (0.1 M) was added 10% Pd/C (0.1 equiv.) in ethyl acetate. The reaction was placed under an atmosphere of hydrogen and stirred for 2 hours. Upon completion, the solution was filtered over a pad of Celite, the pad was washed with methanol, the filtrate was concentrated in vacuo to give methyl 6-(2,6-difluoro-3-hydroxyphenyl)-5-fluoropicolinate as a grey oil in 86% yield. LC/MS=284.0 (M+H), Rt=0.90 min.

Workup

  1. filtrationUpon completion, the solution was filtered over a pad of Celite
  2. washthe pad was washed with methanol
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-88e02eeab29c4d3f88956d15f478dea5
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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