HCID 71143692, compound → HCID 71143792, compound

HRID 1396220Notes

Reaction equation

HRID 1396220 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:30])([CH2:24][N:25]1[CH:29]=[N:28][N:27]=[N:26]1)[C:10]([F:23])([F:22])[C:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[CH2:19][O:20][CH3:21])=[CH:13][N:12]=1>CCO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:30])([CH2:24][N:25]1[CH:29]=[N:28][N:27]=[N:26]1)[C:10]([F:22])([F:23])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:13][N:12]=1

Participants

4

Reactant 1

HCID 71143692HCID 71143692, compound

Product 1

HCID 71143792HCID 71143792, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of (E)-2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-(3-methoxyprop-1-en-1-yl)pyridin-2-yl)-3-(1H-tetrazol-1-yl)propan-2-ol (48; 80 mg, 0.18 mmol) in EtOH (10 mL) was added 10% Pd/C (8 mg), and the mixture was stirred under hydrogen atmosphere for 1 h. The reaction mixture was filtered through a pad of Celite®, the Celite® cake was washed thoroughly with EtOAc (3×30 mL) and then the filtrate was concentrated under reduced pressure to obtain the crude material. Purification by silica gel column chromatography (eluting with 45-50% EtOAc/hexanes) afforded 50 (65 mg, 0.14 mmol, 77%) as a semi-solid.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. washthe Celite® cake was washed thoroughly with EtOAc (3×30 mL)
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto obtain the crude material
  5. customPurification
  6. washby silica gel column chromatography (eluting with 45-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-82f46a80e13740afa0ba044c08a7f8ab
Source dataset
uspto-grants-2014_12
Patent number
US08901121B2

Reaction notes

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