{4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2'-methylbiphenyl-2-YL}methanol → 4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2'-methylbiphenyl-2-carbaldehyde

HRID 336318Notes

Reaction equation

HRID 336318 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])=[C:15]([CH2:26][OH:27])[CH:14]=3)[O:10][N:9]=2)[CH:7]=1>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[CH:14]=[C:15]([CH:26]=[O:27])[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])=[CH:17][CH:18]=3)[O:10][N:9]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 25255481{4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2'-methylbiphenyl-2-YL}methanol

Product 1

HCID 866823724-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2'-methylbiphenyl-2-carbaldehydeYield 93%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese(IV) oxide (111 mg; 1.28 mmol; 10 eq.) was added to a solution of Example 77 (50 mg; 0.13 mmol; 1 eq.) in DCM (5 mL) and the reaction mixture was stirred at room temperature for 4 hours. The suspension was filtered through a pad of CELITE and the solution concentrated in vacuo to afford title compound (46 mg; 93%) as a white solid.

Workup

  1. filtrationThe suspension was filtered through a pad of CELITE
  2. concentrationthe solution concentrated in vacuo

Sources & evidence

ORD record
ord-2581a2293c97484d9411ac7109920911
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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