Pyridine → HCID 17989375, compound

HRID 1353058Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.N1C=CC=CC=1.[CH:19]([N:22]([CH:35]([CH3:37])[CH3:36])[CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][C:27]=1[O:33][CH3:34])([CH3:21])[CH3:20]>CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:11][CH:12]=1)[C:6](=[O:8])[N:32]([C:29]1[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH2:23][N:22]([CH:19]([CH3:21])[CH3:20])[CH:35]([CH3:37])[CH3:36])=[C:27]([O:33][CH3:34])[CH:28]=1)[C:9]2=[O:10]

Participants

Conditions

Temperature: 85 °C

Procedure

4-Bromophthalic anhydride [Apin] (2.27 g, 10 mmol) was dissolved in 1,2-dichloromethane (8 ml), and pyridine (10 mmol, 0.81 ml) was added, followed by 4-(2-diisopropylamino-ethoxy)-3-methoxy-phenylamine [Patent WO-9901127] (2.44 g, 10 mmol) and a catalytic amount of 4-dimethylaminopyridine [Aldrich]. The mixture was heated for 16 h at 85° C. The mixture was evaporated in vacuo and applied to a Biotage Flash40M cartridge, (eluting with dichloromethane-methanol-aqueous ammonia) to give the 5-bromo-2-[4-(2-diisopropylamino-ethoxy)-3-methoxy-phenyl]-isoindole-1,3-dione 3.05 g, 68%, as the trifluoroacetate salt;

Workup

customThe mixture was evaporated in vacuo
washapplied to a Biotage Flash40M cartridge, (eluting with dichloromethane-methanol-aqueous ammonia)

Sources & evidence

ORD record: ord-71eeee85e3f8455e8d459780516673f6
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220777B2

Reaction notes

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