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

HRID 1244979Notes

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

Participants

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

filtrationAt the end of this time, the reaction mixture was filtered
additionwater was added to the filtrate
extractionthis was then extracted with ethyl acetate
extractionThe organic extract
washwas washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated by evaporation under reduced pressure
customto afford a solid which
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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