Hydrochloric Acid → (2E)-3-{1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}acrylic acid

HRID 2264628Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[CH:20]=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(O)(=O)[CH2:23][C:24]([OH:26])=[O:25].N1CCCCC1.Cl>N1C=CC=CC=1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2/[CH:20]=[CH:23]/[C:24]([OH:26])=[O:25])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 0.41 g of 1-[(4-bromophenyl)sulfonyl]-1H-indole-2-carbaldehyde in 3 mL of pyridine, 0.35 g of malonic acid and 0.02 mL of piperidine were added, and the resulting mixture was stirred at 80° C. for 3 hours. After the solution was allowed to cool, 50 mL of water and concentrated hydrochloric acid were added to adjust the pH to pH3, and the precipitated solid was collected by filtration and washed with ethanol to obtain 0.29 g of (2E)-3-{1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl} acrylic acid as a pale yellow solid.

Workup

temperatureto cool
filtrationthe precipitated solid was collected by filtration
washwashed with ethanol

Sources & evidence

ORD record: ord-b437304f375e4183ab5e7701356d6880
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855225B2

Reaction notes

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