HCID 25059128, compound → HCID 25061453, compound

HRID 2089122Notes

Reaction equation

HRID 2089122 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:27][OH:28])[CH:5]=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:18][C:17]3[CH:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:21]=[CH:22][C:16]=3[N:15]=2)=[CH:10][CH:9]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[O:28])[CH:5]=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:18][C:17]3[CH:19]=[C:20]([C:23]([F:25])([F:26])[F:24])[CH:21]=[CH:22][C:16]=3[N:15]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 25059128HCID 25059128, compound

Product 1

HCID 25061453HCID 25061453, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

4.4 g of manganese dioxide (51 mmol) was added to 1.0 g of compound (28) (2.6 mmol) prepared in Example 16 dissolved in 6.5 mL of dichloromethane, and stirred at room temperature for 2 hours. The mixture was filtered with diatomaceous earth, and the filtrate was concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent: chloroform/methanol=30/1) to obtain 0.94 g of 5-chloro-6-[4-(6-trifluoromethyl-1H-benzoimidazol-2-yl)-phenyl]-pyridine-3-carbaldehyde (yield 90%).

Workup

  1. filtrationThe mixture was filtered with diatomaceous earth
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was separated by column chromatography (eluting solvent: chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-f63a8a449ea242f2872c92e044cab44c
Source dataset
uspto-grants-2013_05
Patent number
US08436022B2

Reaction notes

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