Sodium Carbonate → 5-Bromo-2-hydroxy-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dione

HRID 279016Notes

Reaction equation

C([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([Br:28])[C:22]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:29])C1C=CC=CC=1.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.[B+3].O.C(O)C.C([O-])([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O>[Br:28][C:21]1[C:22]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:16]2=[C:17]([CH:20]=1)[C:18](=[O:19])[N:9]([OH:8])[C:10]3=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-benzyloxy-5-bromo-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.23 g, 0.51 mmol, from Example W1) in TFA (5 mL) at 0° C. was added a 1.0 M solution of boron tris(trifluoroacetate) in TFA (3 mL). The reaction was stirred at 0° C. for 2 hours and poured into a water/ethanol solution (1:1). The solution was neutralized with saturated Na2CO3, the resulting precipitate removed by filtration, and chromatographed using chloroform/hexane (10:1) to give 0.10 g of the title compound, mp 170-172° C.

Workup

customat 0° C.
customthe resulting precipitate removed by filtration
customchromatographed

Sources & evidence

ORD record: ord-55fb88b93f8c470b88ce205eed0723ab
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362181B1

Reaction notes

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