HCID 57963218, compound → HCID 57963202, compound

HRID 509957Notes

Reaction equation

HRID 509957 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 (81, 63 g, 240 mmol) in 1.25 L of ethyl acetate, manganese(IV) oxide (210 g, 2.416 mol) was added. The reaction was stirred overnight at room temperature, then filtered through celite and the celite rinsed with ethyl acetate. The combined filtrates were concentrated under vacuum and the resulting solid was triturated with heptane and collected by filtration to provide the desired compound as a white solid (82, 62 g, 238 mmol, 99% yield).

Workup

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

Sources & evidence

ORD record
ord-b251410ba56e4ce2b203f6efc77ddb7b
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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