2-(3-chloro-2-(hydroxymethyl)phenyl)-6-cyclopropyl-8-fluoroisoquinolin-1(2H)-one synthesis
- Product Name:2-(3-chloro-2-(hydroxymethyl)phenyl)-6-cyclopropyl-8-fluoroisoquinolin-1(2H)-one
- CAS Number:1242156-55-3
- Molecular formula:C19H15ClFNO2
- Molecular Weight:343.78
1242156-54-2
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Yield: 96%
Reaction Conditions:
Stage #1:2-chloro-6-(6-cyclopropyl-8-fluoro-1-oxoisoquinolin-2 (1H)-yl)benzaldehyde with lithium triethylborohydride in tetrahydrofuran at 0; for 0.5 h;
Stage #2: with ammonium chloride in tetrahydrofuranProduct distribution / selectivity;
Steps:
252 2-(3-Chloro-2-hydroxymethyl-phenyl)-6-cyclopropyl-8-fluoro-2H-isoquinolin-1-one (IV)
To a suspension of compound III (0.26 g, 0.76 mmol) in 15 ml dry THF which was cooled at 0° C. in an ice bath, was added a solution of superhydride 1M (1.5 ml, 1.5 mmol) in THF. After stirring for 0.5 hour at 0° C. the reaction was quenched with saturated ammonium chloride and diluted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and concentrated to give 0.25 g (96% yield) of IV which was used in the next step without further purification.
References:
Berthel, Steven;Firooznia, Fariborz;Fishlock, Daniel;Hong, Jun-Bae;Lou, Yan;Lucas, Matthew;Owens, Timothy D.;Sarma, Keshab;Sweeney, Zachary Kevin;Taygerly, Joshua Paul Gergely US2010/222325, 2010, A1 Location in patent:Page/Page column 142
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1242157-23-8
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