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 1898908Notes

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 260 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-d63a3e1031e440259afcd8df43250e2e
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571813

Reaction notes

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