Phthalic Anhydride → (E)-2-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}isoindole-1,3-dione

HRID 1821353Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[N:2]1.[C:19]1(=O)[O:24][C:22](=[O:23])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[C:22](=[O:23])[C:21]3[C:20](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:19]2=[O:24])=[N:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

Compound 2 (0.06 g, 0.25 mmol) was dissolved in xylene (2.0 mL) and the solution was added with phthalic anhydride (83 mg, 0.56 mmol) and triethylamine (89 μL, 0.64 mmol), followed by stirring at 60° C. for 2 hours. Then, the reaction mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was triturated in ethanol to obtain Compound 159 (4.0 mg, 4%).

Workup

extractionThen, the reaction mixture was extracted with ethyl acetate
washThe organic layer was sequentially washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was triturated in ethanol

Sources & evidence

ORD record: ord-1878ffb68d2d46f69a3d01ba442c1386
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605272B2

Reaction notes

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