Sodium Hydroxide → 2-(4-Fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole

HRID 1244987Notes

Reaction equation

C(OC([C:6]1[C:7]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[NH:9][CH:10]=1)=O)C.[OH-].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O.O>[F:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[NH:9][CH:10]=[CH:6][C:7]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

15.00 g (48.3 mmol) of 4-ethoxycarbonyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole [prepared as described in Example 1(i) above] were dissolved in a mixture of 90 ml of acetic acid, 30 ml of sulfuric acid and 60 ml of water and the resulting solution was stirred at 100° C. for 16 hours. At the end of this time, the reaction mixture was cooled to room temperature and then made alkaline with a 10% aqueous solution of sodium hydroxide. The resulting mixture was extracted with ethyl acetate and the organic extract was washed with water, dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure to give 11.40 g (yield 99%) of the title compound as a pale red powder.

Workup

temperatureAt the end of this time, the reaction mixture was cooled to room temperature
extractionThe resulting mixture was extracted with ethyl acetate
extractionthe organic extract
washwas washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record: ord-07ba54922e084a65bbc777d68828996e
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122666B2

Reaction notes

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