Pyrrole → HCID 21940679, compound

HRID 1883327Notes

Reaction equation

HRID 1883327 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.I[C:7]1[CH:8]=[C:9]([CH3:14])[CH:10]=[C:11]([CH3:13])[CH:12]=1.[CH3:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(O[CH2:25][CH3:26])(=O)C>>[CH3:13][C:11]1[CH:12]=[C:7]([C:26]2[C:25]3[NH:1][C:2]4[C:19](=[CH:20][CH:5]=[CH:4][CH:3]=4)[C:18]=3[CH:17]=[CH:16][CH:15]=2)[CH:8]=[C:9]([CH3:14])[CH:10]=1

Participants

4

Reactant 3

HCID 8027PyrroleHCID 1409241-Iodo-3,5-dimethylbenzeneHCID 21226206Ethyl acetate hexane

Product 1

HCID 21940679HCID 21940679, compoundYield 99%

Procedure

Using general procedure B, pyrrole (83 μL, 1.2 mmol) was coupled with 5-iodo-m-xylene to give the crude product. Column chromatography (2×15 cm, hexane:ethyl acetate 50:1) provided 0.268 g (99% yield) of the product as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.15 (d, J=7.8 Hz, 2H), 7.41 (m, 4H), 7.28 (m, 2H), 7.18 (s, 2H), 7.11 (s, 1H), 2.43 (s, 6H).

Workup

  1. customto give the crude product

Sources & evidence

ORD record
ord-390de1d9499b453aa2af362a49623008
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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