Phenylboronic Acid → HCID 178515029, compound

HRID 1765367Notes

Reaction equation

HRID 1765367 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=2)[N:3]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[F-].[K+]>CO.[Pd]>[C:16]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:18][C:13]([N:4]2[N:3]=[C:2]([OH:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]2=[O:12])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 178515031HCID 178515031, compound

Product 1

HCID 178515029HCID 178515029, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Hydroxy-2-(4-iodophenyl)-2H-phthalazin-1-one (0.1 g, 0.3 mmol), phenyl boronic acid (0.04 g, 3 mmol), palladium black (0.02 g, 0.2 mmol) and KF (0.1 g, 18 mmol) were dissolved in MeOH (2 ml) and heated at reflux for 7 h. Removal of supernatant palladium by filtration, extraction with H2O and subsequent filtration of the precipitated solid yielded the desired title compound (0.07 g, 78% yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO) 11.88 (1H, s), 8.33 (1H, d), 7.89–8.03 (3H, m), 7.78–7.86 (6H, m), 7.50 (2H, t), 7.39 (1H, t),; MS (ESI+)=315.3 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 7 h
  3. customRemoval of supernatant palladium
  4. filtrationby filtration, extraction
  5. filtrationwith H2O and subsequent filtration of the precipitated solid

Sources & evidence

ORD record
ord-0b5d7938470e4221bbc2b27d629bd4f2
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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