1H-Pyrrole-2-carbonitrile, 1-[4-(bromomethyl)phenyl]- → 2-Cyano-1-[4-((1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl)phenyl]pyrrole

HRID 1450389Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][CH:11]=[C:10]2[C:14]#[N:15])=[CH:5][CH:4]=1.[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CN(C=O)C>[C:14]([C:10]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:20]3[C:16](=[O:26])[C:17]4[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:19]3=[O:21])=[CH:4][CH:5]=2)[CH:13]=[CH:12][CH:11]=1)#[N:15]

Participants

Conditions

Temperature: 70 °C

Procedure

17.0 g (65.1 mmol) 1-(4-(bromomethyl)phenyl)-2-cyanopyrrole (prepared according to P. R. Bovy et al., J. Med Chem. 1993, 36, 101) and 22.0 g (119 mmol) potassium phthalimide were dissolved in 2 ml dry DMF and stirred at 70° C. for 10 h. It was cooled to room temperature, and 600 ml ice-cold water were added. After extraction with ethyl acetate, the organic layer was dried over sodium sulfate, and evaporated in vacuo. The remaining oil solidified upon standing, and it was stirred with t-butylmethylether to give pale yellow crystals of the title compound, which were filtered with suction and dried in vacuo, m.p. 167°-168° C.

Workup

temperatureIt was cooled to room temperature
extractionAfter extraction with ethyl acetate
dry with materialthe organic layer was dried over sodium sulfate
customevaporated in vacuo
stirringit was stirred with t-butylmethylether

Sources & evidence

ORD record: ord-f5e4cc6eba424ea4bd81d0743ae0716f
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05602137

Reaction notes

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