Trifluoroacetate → 5-Bromo-2-hydroxy-7-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione

HRID 567035Notes

Reaction equation

HRID 567035 reaction equation
C([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([Br:23])[CH:22]=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[C:14]3[N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[C:10]1=[O:30])C1C=CC=CC=1.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.[B+3].FC(F)(F)C([O-])=O>C(O)(C(F)(F)F)=O>[Br:23][C:21]1[CH:22]=[C:15]2[C:14]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[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:30]

Participants

5

Reactant 3

HCID 84468TrifluoroacetateHCID 226238972-Benzyloxy-5-bromo-7-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dioneHCID 178525683HCID 178525683, compound

Product 1

HCID 226239255-Bromo-2-hydroxy-7-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dioneYield 28.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Following the procedure of Example 52, 2-benzyloxy-5-bromo-7-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.090 g, 0.19 mmol, from Example T1-B), and a 1.0 M solution of boron tris(trifluoroacetate) in TFA (2 mL) were reacted to give 0.020 g of the title compound as the trifluoroacetate salt, mp 134-136° C.

Sources & evidence

ORD record
ord-45118b03fd384c5f88035b3715fe33bb
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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