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2-(4-fluorophenyl)4-hydroxymethyl-3-(pyridin-4-yl)-1H-pyrrole → 2-(4-Fluorophenyl)-4-formyl-3-(pyridin-4-yl)-1H-pyrrole

HRID 1244979
Notes
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Reaction equation

HRID 1244979 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[C:11]([CH2:19][OH:20])[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1>CS(C)=O.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][CH:10]=[C:11]([CH:19]=[O:20])[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 219227712-(4-fluorophenyl)4-hydroxymethyl-3-(pyridin-4-yl)-1H-pyrrole

Product 1

HCID 219226862-(4-Fluorophenyl)-4-formyl-3-(pyridin-4-yl)-1H-pyrroleYield 69%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

118.00 g (440 mmol) of manganese dioxide were added to a solution of 10.73 g (40 mmol) of 2-(4-fluorophenyl)-4-hydroxymethyl-3-(pyridin-4-yl)-1H-pyrrole [prepared as described in step (ii) above] in 120 ml of dimethyl sulfoxide, after which the resulting mixture was stirred at 50° C. overnight. At the end of this time, the reaction mixture was filtered, water was added to the filtrate, and this was then extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure to afford a solid which was washed with diethyl ether to give 7.35 g (yield 69%) of the title compound as a brown powder.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. additionwater was added to the filtrate
  3. extractionthis was then extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customto afford a solid which
  9. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-65081bb17e63440994c1340791f92709
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07122666B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes