HCID 57963218, compound → HCID 57963202, compound

HRID 1396149Notes

Reaction equation

HRID 1396149 reaction equation
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[C:4]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:3]=1>C(OCC)(=O)C.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[C:4]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:3]=1

Participants

4

Reactant 1

HCID 57963218HCID 57963218, compound

Product 1

HCID 57963202HCID 57963202, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To [2-fluoro-6-(4-methoxy-benzylamino)-pyridin-3-yl]-methanol (44, 63 g, 240 mmol) in 1.25 L of ethyl acetate, manganese(IV) oxide (210 g, 2.416 mol) is added. The reaction is stirred overnight at room temperature, then filtered through celite and the celite rinsed with ethyl acetate. The combined filtrates are concentrated under vacuum and the resulting solid is triturated with heptane and collected by filtration to provide the desired compound as a white solid (45, 62 g, 238 mmol, 99% yield).

Workup

  1. filtrationfiltered through celite
  2. washthe celite rinsed with ethyl acetate
  3. concentrationThe combined filtrates are concentrated under vacuum
  4. customthe resulting solid is triturated with heptane
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-436995677c4249cca3168ec7bb1cff02
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

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