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CAS No. : | 288385-99-9 | MDL No. : | MFCD11977234 |
Formula : | C10H10FNO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VGDKNHRINLDMIS-UHFFFAOYSA-N |
M.W : | 227.19 | Pubchem ID : | 22030743 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With potassium carbonate; In methanol; for 3h;Heating / reflux; | A mixture of 1-(2,3-difluoro-6-nitrophenyl) -propan-2-one (183 g) and potassium carbonate (100 g) in methanol (1L) was heated at reflux for 3 h. The reaction mixture was then cooled and concentrated in vacuo to remove most of the methanol. The residue was diluted with ethyl acetate (1L), filtered and washed with water. The separated aqueous layer was neutralized with 2N HCl and extracted with ethyl acetate (2x500 mL). The combined organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo to give a brown solid. The solid was triturated with diethyl ether and filtered to provide 1-(2-fluoro-3-methoxy-6-nitrophenyl)-propan-2-one (121 g, 71 %) as a yellow solid. LC/MS; (M+H)+ = 228.2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With pyridine hydrochloride; at 20 - 180℃; for 1.25h;Heating / reflux; | A mixture of 1-(2-fluoro-3-methoxy-6-nitrophenyl)-propan-2-one from previous step (454 mg, 21 mmol) and pyridinium chloride (0.9 g, 7.8 mmol) was stirred at 180 C for 75 min. The reaction was cooled to room temperature, diluted with 1N HCl (3mL) and ethyl acetate (10 mL) and filtered. The filtrate was washed with brine (2x), dried and concentrated in vacuo to give 1-(2-fluoro-3-hydroxy-6-nitrophenyl)-propan-2-one (410 mg, 96 %) as a grey solid, which was used without further purification for the next step. LC/MS; (M+H)+ = 214. 1H NMR (CDCl3): delta 2.37 (s, 3H), 4.22 (s, 2H), 6.95 (dd, 1H), 7.95 (d, 1H, J= 9.35 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In water; acetone; | To a solution of <strong>[288385-99-9]3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene</strong> (11.36 g, 50 mmol) in acetone (200 ml) was added 4M aqueous ammonium acetate (700 ml) followed by a solution of titanium trichloride (15% in water, 340 ml) dropwise. The mixture was stirred for 10 minutes at ambient temperature and the mixture was extracted with ether. The organic layer was washed with 0.5N aqueous sodium hydroxide followed by water, brine, dried MgSO4) and the volatiles were removed under vacuum. The residue was purified by column chromatography eluding with methylene chloride to give 4-fluoro-5-methoxy-2-methylindole (8.15 g, 90%). 1H NMR Spectrum: (DMSO) 2.35 (s, 3H); 3.8 (s, 3H); 6.1 (s, 1H); 6.85 (dd, 1H); 7.02 (d, 1H) |
90% | In water; acetone; | To a solution of <strong>[288385-99-9]3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene</strong> (11.36 g, 50 mmol) in acetone (200 ml) was added 4M aqueous ammonium acetate (700 ml) followed by a solution of titanium trichloride (15% in water, 340 ml) dropwise. The mixture was stirred for 10 minutes at ambient temperature and the mixture was extracted with ether. The organic layer was washed with 0.5N aqueous sodium hydroxide followed by water, brine, dried (MgSO4) and the volatiles were removed under vacuum. The residue was purified by column chromatography eluding with methylene chloride to give 4-fluoro-5-methoxy-2-methylindole (8.15 g, 90%). 1H NMR Spectrum: (DMSO) 2.35 (s, 3H); 3.8 (s, 3H); 6.1 (s, 1H); 6.85 (dd, 1H); 7.02 (d, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrogenchloride; sodium methylate; sodium; In tetrahydrofuran; methanol; | A solution of sodium methoxide (freshly prepared from sodium (1.71 g) and methanol (35 ml)) was added to a solution of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (16.2 g, 62 mmol), (prepared as described above), in methanol (200 ml) cooled at 5 C. The mixture was left to warm to ambient temperature and was stirred for 3 days. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and 2N hydrochloric acid (1ml). The organic layer was concentrated to a total volume of 100 ml and THF (100 ml) and 6N hydrochloric acid (25 ml) were added. The mixture was stirred for 1 hour at ambient temperature. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluding with ethyl acetate/petroleum ether (3/7) to give 3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene (12.7 g, 90%). MS-ESI: 250 [MNa]+ 1H NMR Spectrum: (CDCl3) 2.38 (s, 3H); 4.0 (s, 3H); 4.25 (s, 2H); 7.0 (dd, 1H); 8.05 (d, 1H) |
90% | With hydrogenchloride; sodium methylate; sodium; In tetrahydrofuran; methanol; | A solution of sodium methoxide (freshly prepared from sodium (1.71 g) and methanol (35 ml)) was added to a solution of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (16.2 g, 62 mmol), (prepared as described above), in methanol (200 ml) cooled at 5 C. The mixture was left to warm to ambient temperature and was stirred for 3 days. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and 2N hydrochloric acid (1 ml). The organic layer was concentrated to a total volume of 100 ml and THF (100 ml) and 6N hydrochloric acid (25 ml) were added. The mixture was stirred for 1 hour at ambient temperature. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluding with ethyl acetate/petroleum ether (3/7) to give 3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene (12.7 g, 90%). MS-ESI: 250 [MNa]+ 1H NMR Spectrum: (CDCl3) 2.38 (s, 3H); 4.0 (s, 3H); 4.25 (s, 2H); 7.0 (dd, 1H); 8.05 (d, 1H) |
90% | With hydrogenchloride; sodium methylate; sodium; In tetrahydrofuran; methanol; | A solution of sodium methoxide (freshly prepared from sodium (1.71 g) and methanol (35 ml)) was added to a solution of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (16.2 g, 62 mmol), (prepared as described above), in methanol (200 ml) cooled at 5 C. The mixture was left to warm to ambient temperature and was stirred for 3 days. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and 2N hydrochloric acid (1 ml). The organic layer was concentrated to a total volume of 100 ml and THF (100 ml) and 6N hydrochloric acid (25 ml) were added. The mixture was stirred for 1 hour at ambient temperature. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluding with ethyl acetate/petroleum ether (3/7) to give 3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene (12.7 g, 90%). MS-ESI: 250 [MNa]+ 1H NMR Spectrum: (CDCl3) 2.38 (s, 3H); 4.0 (s, 3H); 4.25 (s, 2H); 7.0 (dd, 1H); 8.05 (d, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 3: preparation of 1-(2-fluoro-3-methoxy-6-nitrophenyl)propan-2-one In a 100mL round-bottomed flask 2g 1-(2,3-difluoro-6-nitrophenyl)propan-2-one prepared from Step 2 was added to a solution of sodium methoxide in methanol(40mL), wherein the solution of sodium methoxide in methanol was prepared by slowly adding 2.27g Na to methanol with sitrring in an ice bath and stirring for 1h at 50C after the addition. The mixture was reacted for 1h at room temperature before the reaction was complete, and quenched by adding 1mL water and extracted with dichloromethane. The organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound. 1H NMR(400MHz,DMSO-d6) delta ppm:8.04-8.07(m,1H),7.31-7.35(m,1H),4.20-4.21(d, 2H),3.98(s,3H),2.28(s,3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol; palladium on activated charcoal; at 20℃; for 36h; | Step 4: preparation of 2-methyl-4-fluoro-5-methoxy-1H-indole In a 100mL round-bottomed flask 1.9g <strong>[288385-99-9]1-(2-fluoro-3-methoxy-6-nitrophenyl)propan-2-one</strong> prepared from Step 3 was added to 15mL methanol and dissolved, and 190mg palladium on carbon was added. The mixture was reacted for 36h at room temperature, then the reaction was stopped. The mixture was filtered, and concentrated to give the title compound. 1H NMR(400MHz,DMSO-d6) delta ppm: 11.01(br,1H),6.99-7.01(d,1H),6.853(m,1H), 6.10-6.11 (t,1H),3.79(s,3H),2.35(s,3H). |
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