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6-Fluoro-3, 4-dihydro-2H-naphthalen-1-one Heat a mixture of 4- (3-fluoro-phenyl)-butyric acid (1.92 g, 10.5 mmol) and polyphosphoric acid (2 g) at 110°C under nitrogen for two hours. After cooling to room temperature, quench with water, dilute with ether, wash with saturated aqueous sodium bicarbonate (2x), dry over anhydrous sodium sulfate, and concentrate to obtain the title compound (1.51 g, 87percent). NMR (400 MHz, CDCl3) : 8 2.16 (m, 2H), 2. 64 (t, 2H), 2.97 (t, 2H), 6.92 (dd, 1H), 6.99 (dt, 1H), 8. 04 (dd, 1H).
53.97%
at 85℃; for 2.25 h;
Step 36-Fluoro-3,4-dihydro-2H-naphthalen-l-one A solution of methanesulfonic acid (75 mL) and P2Os was stirred at 85 ° C for 15 minutes, at which point most of the P2Os had dissolved. An additional 15 mL of methanesulfonic acid was added dropwise, and the mixture was stirred at 85 ° C for 2 hours. The reaction mixture was poiured into 500 mL of water and extracted twice with 400 mL of EtOAc. The combined organic layers were washed with saturated NaHCO3, water, and saturated brine, and then dried over MgSO4. The solvent was removed under reduced pressure to give an oil that was eluted through silica gel using hexanes/EtOAc (9:1). Removal of solvent under reduced pressure yielded 6.06 g, 36.91 mmol, 53.97percent) of 6-fluoro-3,4-dihydro-2H-naphthalen~l-one as a yellow oil. MS: 165 (M+H)+.
53.97%
at 85℃; for 2 h;
Step 36-Fluoro-3,4-dihvdro-2H-naphthalen- 1 -oneA solution of methanesulfonic acid (75 mL) and P2O5 was stirred at 85 ° C for 15 minutes, at which point most of the P2O5 had dissolved. An additional 15 mL of methanesulfonic acid was added dropwise, and the mixture was stirred at 85 ° C for 2 hours. The reaction mixture was poiured into 500 mL of water and extracted twice with 400 mL of EtOAc. The combined organic layers were washed with saturated NaHCψ3, water, and saturated brine, and then dried over MgSO4. The solvent was removed under reduced pressure to give an oil that was eluted through silica gel using hexanes/EtOAc (9:1). Removal of <n="44"/>solvent under reduced pressure yielded 6.06 g, 36.91 mmol, 53.97percent) of 6-fluoro-3,4- dihydro-2H-naphthalen-l-one as a yellow oil. MS: 165 (M+H)+.
3,3,3-trifluoro-2-(6-fluoro-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-2-hydroxy-<i>N</i>-(4-methyl-1-oxo-1<i>H</i>-benzo[<i>d</i>][1,2]oxazin-6-yl)-propionamide[ No CAS ]
3,3,3-trifluoro-2-(6-fluoro-3,4-dihydro-naphthalen-1-ylmethyl)-2-hydroxy-<i>N</i>-(4-methyl-1-oxo-1<i>H</i>-benzo[<i>d</i>][1,2]oxazin-6-yl)-propionamide[ No CAS ]
7-{2-[4-(6-fluoro-naphthalen-1-yl)-2-methyl-piperazin-1-yl]-ethyl}-7-methyl-4,7-dihydro-5<i>H</i>-thieno[2,3-<i>c</i>]pyran-2-carboxylic acid amide[ No CAS ]
7-{2-[4-(6-fluoro-naphthalen-1-yl)-2,2-dimethyl-piperazin-1-yl]-ethyl}-4,7-dihydro-5<i>H</i>-thieno[2,3-<i>c</i>]pyran-2-carboxylic acid amide[ No CAS ]
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