[5-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazol-3-yl]-methanol → 5-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazole-3-carbaldehyde

HRID 509965Notes

Reaction equation

HRID 509965 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[C:10]([CH2:22][OH:23])[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=2)=[CH:4][CH:3]=1>[O-2].[Mn+4].[O-2].ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[C:10]([CH:22]=[O:23])[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 58259462[5-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazol-3-yl]-methanol

Product 1

HCID 582591365-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazole-3-carbaldehydeYield 98.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask, [5-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazol-3-yl]-methanol (112, 1.6 g, 4.2 mmol) was combined with 300 mL of dichloromethane and manganese(IV) oxide (0.61 g, 7.0 mmol) and stirred overnight under nitrogen. The reaction was filtered through celite and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with 10-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (113, 1.4 g). 1H NMR was consistent with the compound structure.

Workup

  1. filtrationThe reaction was filtered through celite
  2. concentrationthe filtrate concentrated under vacuum
  3. customThe resulting material was purified by silica gel column chromatography
  4. washeluting with 10-100% ethyl acetate in hexane
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-82c4454fbf81408cbbd7e7bf7471b828
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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