HCID 70655166, compound → HCID 70654961, compound

HRID 879130Notes

Reaction equation

HRID 879130 reaction equation
[O:1]=[S:2]1(=[O:26])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[C:12]([F:14])[C:11]([C:15]3[N:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[CH:17][C:16]=3[F:24])=[C:10]([F:25])[CH:9]=2)[CH2:4][CH2:3]1>CCO.[Pd]>[O:26]=[S:2]1(=[O:1])[CH2:3][CH2:4][CH:5]([C:8]2[CH:9]=[C:10]([F:25])[C:11]([C:15]3[N:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[CH:17][C:16]=3[F:24])=[C:12]([F:14])[CH:13]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 70655166HCID 70655166, compound

Product 1

HCID 70654961HCID 70654961, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To a degassed solution of 6-(4-(1,1-dioxido-3,6-dihydro-2H-thiopyran-4-yl)-2,6-difluorophenyl)-5-fluoropicolinic acid (1.0 equiv.) in EtOH (0.10 M) was added Pd/C (0.1 equiv.). The mixture was stirred at rt under H2 for 16 hrs. Add Pd/C (0.1 equiv.) and the reaction was stirred for additional 16 hrs. The reaction was filtered and concentrated to yield 6-(4-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-2,6-difluorophenyl)-5-fluoropicolinic acid in 100% yield. LC/MS=386.0 (M+H), Rt=0.64 min.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-829d1822514a4efe9d559c6afdda9899
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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