Triphenylphosphine → 5-Bromo-2-[2-(quinolin-2-yl)ethyl]phthalazin-1(2H)-one
Reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Br:34][C:35]1[CH:44]=[CH:43][CH:42]=[C:41]2[C:36]=1[CH:37]=[N:38][NH:39][C:40]2=[O:45].[N:46]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:49]=[CH:48][C:47]=1[CH2:56][CH2:57]O>C1COCC1.O>[Br:34][C:35]1[CH:44]=[CH:43][CH:42]=[C:41]2[C:36]=1[CH:37]=[N:38][N:39]([CH2:57][CH2:56][C:47]1[CH:48]=[CH:49][C:50]3[C:55](=[CH:54][CH:53]=[CH:52][CH:51]=3)[N:46]=1)[C:40]2=[O:45]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of PPh3 (699 mg, 2.67 mmol) in THF (50 mL) and DIAD (198 mg, 0.98 mmol), 5-bromo-2H-phthalazin-1-one (300 mg, 1.33 mmol) and then 2-quinolin-2-yl-ethanol from example a1 (254 mg, 1.46 mmol) were added dropwise at 15° C. under nitrogen. The mixture was stirred at room temperature overnight. Water was added and the mixture was extracted with EtOAc. The organic phase was washed with HCl (1 N). The aqueous phase was basified and extracted with DCM. The organic phase was washed with a NaHCO3-solution, dried over Na2SO4, filtered and concentrated. The crude product was recrystallized from EA and dried to give the title compound as bright beige solid (300 mg, 59.2% yield).
Workup
- extractionthe mixture was extracted with EtOAc
- washThe organic phase was washed with HCl (1 N)
- extractionextracted with DCM
- washThe organic phase was washed with a NaHCO3-solution
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was recrystallized from EA
- customdried
Sources & evidence
- ORD record
- ord-1d3ca820680a4a4bab930a749a5760c2
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273068B2
Reaction notes
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