Potassium Carbonate → 7-(4-(trifluoromethoxy)phenyl)phthalazin-1(2H)-one

HRID 1477216Notes

Reaction equation

HRID 1477216 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[N:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[F:13][C:14]([F:26])([F:25])[O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[F:13][C:14]([F:25])([F:26])[O:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[N:7][NH:8][C:9]3=[O:12])=[CH:4][CH:3]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 222653177-bromo-2H-phthalazin-1-one

Product 1

HCID 709746217-(4-(trifluoromethoxy)phenyl)phthalazin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-bromophthalazinone (1.09 g, 4.84 mmol), 4-trifluoromethoxyphenyl boronic acid (1.20 g, 5.81 mmol), dppf(Pd)Cl2 (177 mg, 0.242 mmol), potassium carbonate (1.34 g, 9.68 mmol) in degassed toluene (4 mL), degassed water (2 mL) and degassed isopropanol (2 mL) was heated at 90° C. for 12 hours. The layers were separated, the organic layer was concentrated and the residue was purified by trituration with hexanes/ethyl acetate to provide 7-(4-(trifluoromethoxy)phenyl)phthalazin-1(2H)-one as a white powder. C15H9F3N2O2. 307.2 (M+1).

Workup

  1. customdegassed water (2 mL)
  2. customdegassed isopropanol (2 mL)
  3. customThe layers were separated
  4. concentrationthe organic layer was concentrated
  5. customthe residue was purified by trituration with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-22d7484f07f246b29c9664b66bab786c
Source dataset
uspto-grants-2016_08
Patent number
US09403782B2

Reaction notes

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