Water → 2-[6-(3-Fluoro-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-propionic Acid Ethyl Ester

HRID 2415436Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[NH:12][CH2:11][CH2:10]2.[H-].[Na+].[CH2:23]([O:25][C:26](=[O:30])[CH:27](Br)[CH3:28])[CH3:24].O>CN(C=O)C>[CH2:23]([O:25][C:26](=[O:30])[CH:27]([N:12]1[CH2:11][CH2:10][C:9]2[C:14](=[CH:15][CH:16]=[C:7]([O:6][CH2:5][C:4]3[CH:18]=[CH:19][CH:20]=[C:2]([F:1])[CH:3]=3)[CH:8]=2)[C:13]1=[O:17])[CH3:28])[CH3:24]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 6-(3-fluoro-benzyloxy)-3,4-dihydro-2H-isoquinolin-1-one (0.100 g, 0.369 mmol) and sodium hydride (55%, 22 mg, 0.51 mmol) in N,N′-dimethylformamide was heated at 70° C. for 1 h. Then ethyl-2-bromopropionate (0.072 mL, 0.55 mmol) was added and the resulting mixture was heated at 80° C. overnight. After cooling to room temperature, water was added and the reaction was extracted with dichloromethane. After drying of the organic layer with MgSO4, filtration and evaporation, the residue was purified by chromatography (SiO2, hexane/ethyl acetate 1:0 to 3:2 v:v gradient) to give the title compound as a white solid (0.095 g, 69%). MS: m/e=372.3 (M+H+).

Workup

temperaturethe resulting mixture was heated at 80° C. overnight
temperatureAfter cooling to room temperature
extractionthe reaction was extracted with dichloromethane
dry with materialAfter drying of the organic layer with MgSO4, filtration and evaporation
customthe residue was purified by chromatography (SiO2, hexane/ethyl acetate 1:0 to 3:2 v:v gradient)

Sources & evidence

ORD record: ord-cfc7eaa6de8e4401959b105d83a53e37
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818774B2

Reaction notes

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