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CAS No. : | 1678-49-5 | MDL No. : | MFCD00085925 |
Formula : | C5H3BrN2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YZQMKADIENBVLH-UHFFFAOYSA-N |
M.W : | 218.99 | Pubchem ID : | 548521 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
37% | With tetrabutyl ammonium fluoride In tetrahydrofuran; dimethyl sulfoxide at 125℃; | Example 3 (0054) Non-radioactive fluorination of 3-bromo-4-nitropyridine N-oxide (8): 10 μL of 1 M TBAF solution in THF (10 μmol, 0.5 eq.) was added to a solution of a 3-bromo-4-nitropyridine N-oxide (98+percent, Alfa Aesar) (20 μmol, 1 eq.) in 500 μL of anhydrous DMSO in a 2 mL HPLC vial. The reaction was analyzed by HPLC (conditions B). Retention times: 3-bromo-4-nitropyridine N-oxide (8)=11.84 min, 3-fluoro-4-nitropyridine N-oxide (9)=7.93 min. Retention time for the product matched within 0.05 min the reference standard. Identity of the product was confirmed by HR-MS (m/z M+ exp.: 158.0141, calc.: 158.0128) and 1H, 13C and 19F NMR. Product amount was calculated from the area under the curve of the HPLC UV2 trace using a calibration curve. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.0% | With sulfuric acid; nitric acid; at 0 - 90℃; for 2h; | Step 2: 3-bromo-4-nitropyridin-/V-oxide; Concentrated nitric acid (128 ml) and concentrated sulfuric acid (77 ml) were slowly added to a solution of 3-bromopyridin-/V-oxide (31.9 g, 181.0 mmol) prepared in Step 1 in concentrated sulfuric acid (77 ml), while maintaining the temperature at 0C ~ 5C. The reaction mixture was stirred at 90 C for 2 hours and then cooled to room temperature. The reaction mixture was added to 1000 ml of ice water, which was then brought to pH 8 with 50 % sodium hydroxide solution. The resulting precipitate was filtered and dried to give the titled compound as a yellow solid (29.3 g, 72.0 %).TLC; n-hexane/ethyl acetate = 1/1 (v/v); Rf = 0.31 H-NMR (CDC1) 6 8.6(s, 1H) 8.4-7.9(m, 2H) |
72.0% | 128 ml of cone, nitric acid and 77 ml of cone, sulfuric acid were slowly added at 0 -5 0C to a solution of 3-bromopyridine-/V-oxide (31.9 g, 0.181 mol) prepared in Step 1 in 77 ml of cone, sulfuric acid. The reaction mixture was stirred at 90 0C for 2 hours, and then cooled to room temperature. The reaction mixture was added to 1 L of ice water, brought to pH 8 with a sodium hydroxide solution (50 %) and then filtered. The isolated precipitate was dried to give the titled compound (29.3 g, 72.0 %) as a yellow solid.[179] Rf (n-hexane/ethyl acetate = 1/1, v/v) = 0.3[180] 1H-NMR (400MHz, CDCl ) δ 8.6(s,lH), 8.4-7.9(m,2H) | |
16 g | With sulfuric acid; potassium nitrate; at 110℃; for 12h; | To a solution of 3-bromo pyridine (25 g, 0.158 mol) in glacial acetic acid (150 mL) was added hydrogen peroxide (50 wt.% in H2O, 150 mL) at 10-20C and the reaction mixture was stirred at rt for 30 mins and further heated to reflux for 16 h. The reaction mixture was concentrated to obtain 25 g of 3-bromopyridine 1 -oxide which was taken to the next step without further purification. To the solution of 3-bromopyridine 1-oxide (25 g, 0.144 mol) obtained above in cone H2SO4 (175 mL) was added KNO3 (175 g, 1.73 mol) portion wise and the reaction mixture was heated at 110 C for 12 h. The reaction mixture was slowly poured onto ice and the precipitate obtained was filtered and dried to afford 16 g of 3-bromo-4-nitropyridine 1- oxide. A solution of 3-bromo-4-nitropyridine 1-oxide (16 g, 73.06 mmol) in methanol (50 mL) was saturated with HCl gas and the reaction mixture was stirred at rt for 2 h. The reaction mixture was neutralized with NaHCC and concentrated. The concentrate was extracted with 5% MeOH in CH2CI2. The organic layer was separated, dried, filtered and concentrated to afford 12 g of the title product. XH NMR (300 MHz,CDCl3): δ 8.43 (s, 1H), 8.09-8.06 (d, J = 6.9 Hz, 1H), 7.36-7.28 (d, / = 7.2 Hz, 1H); MS (m/z): 210.12 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In tetrahydrofuran; at 20℃; | To a slurry of 5.00 g (22.8 mmol) of 3-bromo-4- nitropyridine-1-oxide in 50 mL of tetrahydrofuran (THF) was slowly added 68.5 mL (137 mmol) of methylamine (2.0 M solution in THF). The reaction mixture was stirred overnight at room temperature and concentrated in vacuo. The thus obtained residue was dissolved in 250 mL of dichloromethane and washed with 100 mL of saturated aqueous sodium bicarbonate and 100 mL of water. The combined aqueous layers were extracted with 100 mL of dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give 3.78 g (98%) of the title compound. 1H NMR (CDC13) 8 3. 03 (d, J = 5.3 Hz, 3H), 7. 48 (d, J = 7.2 Hz, 1H), 7.94 (s, 1H), 8.02 (d, J = 7.2 Hz, 1H) ; MS Calcd.: 169; Found: 170 (M+H). |
In ethanol; at 90℃; for 0.333333h; | To a solution of 3-bromo-4-nitropyridine N-oxide (0.5 g, 2.28 mmol) in 2 ml ethyl alcohol, methylamine (33% weight in ethyl alcohol) (0.57 ml, 4.56 mmol) was added and the mixture was heated by microwave under 900C for 20 minutes. The mixture was concentrated under reduced pressure to yield Methyl-(4-nitro-1-oxy-pyridin-3-yl)-amine (0.38 g); MS+ 170.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 90℃; for 3h; | [0545] 1.300 g (5.940 mmol) 3-bromo-4-nitro-pyridine-1-oxide and 0.980 g (7.430 mmol) 3-pyrrolidin-1-yl-propylamine was added to a suspension of 0.820 g (5.940 mmol) potassium carbonate in 20 mL DMF and the mixture was stirred for 3 hours at 90 C. The solvent was evaporated i. vac. and the residue purified by column chromatography (Alox (neutral, activity II-III), gradient dichloromethane/MeOH 100:0→95:5 v/v) (0.950 g, 60% of theory). [0546] 0.900 g (3.380 mmol) of the intermediate product was added to a suspension of 300 mg Pd/C in 10 mL EtOH and the mixture was hydrogenated for 4.5 hours at RT and 50 psi H2-pressure. The catalyst was removed by filtration and the filtrate evaporated i. vac. The product is present in admixture with the corresponding pyridine-N-oxide and was used in the next reaction step without any further purification. [0547] Yield: 35% of theory [0548] ESI-MS: (M+H)+=221 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; | a 3-Dimethylamino-methylene-1,5-diazainden-2-one 3-Bromo-4-nitropyridine-1-oxide was prepared according to the procedure of Daisley and Hanbali (Org. Prep. Proced. Int. 1983, 15, 280) and converted to 1,5-diazaindene via the method of Sakamoto et. al. (Heterocycles 1992, 34, 2379). 1,5-Diazaindene was subsequently converted to 1,5-diazainden-2-one hydrobromide via the procedure out lined by Robinson and Donahue (J. Org. Chem. 1991, 56, 4805) and reaction of this with N,N-dimethylformamide-di-t-butyl acetal in DMF gave 3-dimethylamino-methylene-1,5-diazainden-2-one (as described for the preparation of 3-dimethylamino-methylene-1,6-diazainden-2-one): 1H NMR (DMSO-d6): δ3.35 (s, 6H), 7.13 (d, J=6.1 Hz, 1H), 8.09 (s, 1H), 8.20 (d, J=6.1 Hz, 1H), 8.57 (s, 1H), 11.50 (s, 1H); C10H11N3O: APES+MS: m/z 190 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium tert-butylate; In tert-butyl alcohol; at 20℃; for 12h; | Preparation 2. 2-(4-nitropyridin-3-yl)-1,2,3,4-tetrahydroisoquinoline; Step 1: 2-(4-nitro-l-oxypyridin-3-yl)-1,2,3,4-tetrahydroisoquinoline; 3-Bromo-4-nitropyridin-/V-oxide (1.0 g, 4.53 mmol) prepared in Step 2 of Preparation 1 was added to the mixture of te?t-butanol (30 ml), potassium te?t-butoxide (507 mg, 4.53 mmol), and 1,2,3,4-tetrahydroisoquinoline (0.79 ml, 6.34 mmol). The reaction mixture was stirred for 12 hours at room temperature. Water (10 ml) was added to the reaction mixture, which was then extracted with ethyl acetate (100 ml). The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate / n-hexane = 1/1 (v/v)) to give the titled compound as a yellow solid (600 mg).TLC; n-hexane/ethyl acetate = 1/1 (v/v); Rf = 0.21 H-NMR (CDC1) 6 8.13(s, 1H), 7.83(d, 1H), 7.7l(d, 1H), 7.24(m, 3H), 7.09(m, 1H), 4.32(s, 2H), 3.46(t, 2H), 3.06(t, 2H) | |
With potassium tert-butylate; In tert-butyl alcohol; at 20℃; for 12h; | 3-Bromo-4-nitropyridine-/V-oxide (1.0 g, 4.53 mmol) prepared in Step 2 was added to a mixture of tert-butanol (30 ml), potassium teτt-butoxide (507 mg, 4.53 mmol), and 1,2,3,4-tetrahydroisoquinoline (0.79 ml, 6.34 mmol). The reaction mixture was stirred for 12 hours at room temperature. Water (10 ml) was added to the reaction mixture, which was then extracted with ethyl acetate (100 ml). The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/ n-hexane = 1/1, v/v) to give the titled compound (600 mg) as a yellow solid.[ 184] Rf (n-hexane/ethyl acetate = 1/1 , v/v) = 0.2[185] 1H-NMR (400MHz, CDCl ) δ 8.13(s,lH), 7.83(d,lH), 7.71(d,lH), 7.24(m,3H),7.09(m,lH), 4.32(s,2H), 3.46(t,2H), 3.06(t,2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14.6% | With potassium hydroxide; Tris(3,6-dioxaheptyl)amine; potassium carbonate; In toluene; at 20℃; for 1h; | Step 3: 3-(4-fluorobenzyloxy)-4-nitropyridin-A^-oxide; 3-Bromo-4-nitropyridin-/V-oxide (2.0 g, 9.05 mmol) prepared in Step 2, 4-fluorobenzyl alcohol (1.48 ml, 13.57 mmol), potassium carbonate (1.25 g, 9.05 mmol), and potassium hydroxide (2.03 g, 36.2 mmol) were added to 500 ml of anhydrous toluene. Tris[2-(2-methoxyethoxy)ethyl]amine (0.29 ml, 0.90 mmol) was added to the reaction mixture, which was then stirred for 1 hour at room temperature. The reaction mixture was filtered and concentrated. The resulting residue was purified with silica gel column chromatography (ethyl acetate / n-hexane =1/1 (v/v)) to give the titled compound as a white solid (500 mg, 14.6 %).TLC; n-hexane/ethyl acetate = 1/1 (v/v); Rf = 0.21 H-NMR (CDC1) b 8.5(s, 1H), 8.33(d, 1H), 8.20(m, 2H), 8.17(d, 1H), 8.15 (m, 2H), 5.21(s, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methylamine; In trichlorophosphate; | EXAMPLE 40 3-Methyl-2-(2,4-dimethoxyphenyl)-1H-imidazo[4,5-c]pyridine and its hydrochloride A mixture of 2,4-dimethoxybenzoic acid and 3-methylamino-4-amino-pyridine (prepared from 3-bromo-4-nitropyridine-N-oxide and methylamine followed by reduction) in phosphorus oxychloride was refluxed for 4 hours. After cooling the solid was triturated with ether and then partitioned between chloroform and saturated sodium bicarbonate. After drying over magnesium sulphate the solvent was evaporated and the residue chromatographed on silica gel. Recrystallisation from benzene-petrol gave the title base, m.p. 162-163 C. An acetone solution of the base was treated with ethereal HCl to give the title hydrochloride, m.p. 235-237 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In ethanol; for 16h;Heating / reflux; | METHOD 4; Example 88; Synthesis of 4-nitro-3-(piperidin-l-yl)pyridine 1 -oxide[0206] 3-bromo-4-nitropyridine-N-oxide (1.0 equiv.) and piperidine (2.0 equiv.) in ethanol, at a concentration of 0.2 M, was heated at reflux for 16 hours. Upon cooling the ethanol was removed in vacuo. The residue was partitioned between EtOAc and Na2CO3 (sat), and washed further with H2O, NaCl(sat.), was dried over MgSO4, was filtered and the volatiles were removed in vacuo yielding 4-nitro-3-(piperidin-l- yl)pyridine 1 -oxide (92%). LCMS (m/z): 224.0 (MH+); LC R, = 2.48 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;Aliquat 336; In acetone; for 6h;Heating / reflux; | A mixture of 3 g (13.7 mmol) of 3-bromo-4-nitropyridine 1-oxide, 2.1 g (13.7 mmol) of methyl 5-hydroxynicotinate, and 5.7 g (41.1 mmol) of potassium carbonate in 60 ml of acetone containing 1 drop of Aliquat-336 is stirred at reflux for 6 hours. The mixture is diluted with acetone and filtered through magnesium silicate. The solvent is removed and the 2.6 g of 3-(5-(methoxycarbonyl)pyridin-3-yloxy)-4-nitropyridine 1-oxide is obtained after chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In tetrahydrofuran; at 0℃; | Ethyl cyanoacetate (0.486 mL, 4.57 mmol) was added dropwise at O0C to a suspension of 0.11 g (4.57 mmol) of 60% sodium hydride in 10 mL THF. Subsequent addition of 3- bromo-4-nitropyridine N-oxide (1 g, 4.57 mmol) in 5 mL THF resulted in a deep purple colour. The reaction mixture was concentrated and the residue (1.15 g) was used without any further purification. LCMS (1 ): Rt 0.98 min; m/z 250 [M-H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | In ethanol; at 60℃; for 18h; | 3-[(4-Chlorophenyl)amino]-4-nitropyridin-1-ium-1-olate <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (1.00 g, 4.57 mmol) and 4-chloroaniline (1.75 g, 13.7 mmol) were dissolved in EtOH and heated at 60 C. for 18 h. The reaction mixture was cooled to 0 C. and the precipitate was collected by filtration and washed with cold EtOH to give the title compound as an orange solid (317 mg, 26.1%). LCMS (ES+): 266.1 [MH]+. HPLC: Rt 5.44 min, 99.5% purity. |
31.2% | In ethanol; at 60℃; for 18h; | INTERMEDIATE 1 3-[(4-Chlorophenyl)amino]-4-nitropyridin-1-ium-1-olate<strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (15.0g, 68.5mmol) and 4-chloroaniline (26.2g, 205mmol) were dissolved in EtOH (100ml_) and heated to 60C for 18h. The reaction mixture was cooled in an ice/water bath and the precipitate was collected by filtration and slurried in EtOH (80ml_) at 60C for 2h to give the title compound as an orange solid (5.68g, 31.2%). LCMS (ES+): 266.0 [M+H]+. HPLC: Rt 5.45 min, 98.3% purity. |
26.1% | In ethanol; at 60℃; for 18h; | 3-[(4-Chlorophenyl)amino]-4-nitropyridin-1-ium-1-olate 3-Bromo-4-nitropyridine A/-oxide (1.00g, 4.57mmol) and 4-chloroaniline (1.75g, 13.7mmol) were dissolved in EtOH and heated at 60C for 18h. The reaction mixture was cooled to 0C and the precipitate was collected by filtration and washed with cold EtOH to give the title compound as an orange solid (317mg, 26.1 %). LCMS (ES+): 266.1 [MH]+. HPLC: Rt 5.44min, 99.5% purity. |
26.1% | In ethanol; at 60℃; for 18h; | <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (l.OOg, 4.57 mmol) and 4-chloroaniline (1.75 g, 13.7 mmol) were dissolved in EtOH and heated at 60 C for 18h. The reaction mixture was cooled to 0 C and the precipitate was collected by filtration and washed with cold EtOH to give the title compound as an orange solid (317 mg, 26.1%). LCMS (ES+): 266.1 [MH]+. HPLC: Rt 5.44 min, 99.5% purity. |
23.3% | In ethanol; at 60℃; for 18h; | <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (1 O.Og, 45.7mmol) and 4-chloroaniline (1 7.5g, l37mmol) were dissolved in EtOH (lOOmL) and heated to 60C for 18h. The reaction mixture was cooled to RT and the precipitate was collected by filtration to give the title compound as an orange solid (2.83g, 23.3%). LCMS (ESj:266.0 [MH]. HPLC: Rt 5.52mm, 100% purity. |
In ethanol; | 3-[(4-Chlorophenyl)amino]-4-nitropyridin-1-ium-1-olate <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (1.00 g, 4.57 mmol) and 4-chloroaniline (1.75 g, 13.7 mmol) were dissolved in EtOH and heated at 60 C. for 18 h. The reaction mixture was cooled to 0 C. and the precipitate was collected by filtration and washed with cold EtOH to give the title compound as an orange solid (317 mg, 26.1%). LCMS (ES+): 266.1 [MH]+. HPLC: Rt 5.44 min, 99.5% purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetonitrile; at 0 - 20℃;Inert atmosphere; | 3-Bromo-4-nitropyridine 1-oxide (4.57 mmol, 1.0 g) was added to an oven dried 200 mL round-bottomed flask equipped for stirring under nitrogen. Acetonitrile (30 mL) and K2CO3 (11.42 mmol, 1.60 g) were added and the resultant solution was cooled to 0 C. with an ice bath.3-Methoxypropan-1-amine (5.02 mmol, 0.514 mL) was then added drop-wise via syringe and the resultant solution was stirred at 0 C. for 0.5 hr. The ice bath was removed and the reaction was allowed to warm to room temperature and stir for 16 hr. The reaction solution was filtered over Celite. The filtrate was collected, concentrated, and dried in-vacuo affording 3-(3-methoxypropylamino)-4-nitropyridine 1-oxide (36A) as dark brown oil which was used without further purification. ESI-MS: mh 228.3 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In ethanol; at 20℃; | 3-bromo-4-nitropyridine 1-oxide (CAS 1678-49-5, 10 g, 46 mmol) was dissolved in ethanol (400 mL). To the resulting mixture 3-methylbutan-l-amine (21.8 g, 250 mmol) was slowly added. The reaction mixture was stirred overnight at room temperature and concentrated under reduced pressure. The residue was dissolved in CH2CI2 (500 mL) and washed with a saturated aqueous solution of NaHC03 (500 mL). The combined aqueous layers were extracted with CH2CI2 (3 X 150 mL). The combined organic layers were dried over Na2S04 and concentrated to give the intermediate 34-1 (9.8 g, 94%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12 g | With hydrogenchloride; In methanol; at 22 - 26℃; for 2h; | To a solution of 3-bromo pyridine (25 g, 0.158 mol) in glacial acetic acid (150 mL) was added hydrogen peroxide (50 wt.% in H2O, 150 mL) at 10-20C and the reaction mixture was stirred at rt for 30 mins and further heated to reflux for 16 h. The reaction mixture was concentrated to obtain 25 g of 3-bromopyridine 1 -oxide which was taken to the next step without further purification. To the solution of 3-bromopyridine 1-oxide (25 g, 0.144 mol) obtained above in cone H2SO4 (175 mL) was added KNO3 (175 g, 1.73 mol) portion wise and the reaction mixture was heated at 110 C for 12 h. The reaction mixture was slowly poured onto ice and the precipitate obtained was filtered and dried to afford 16 g of 3-bromo-4-nitropyridine 1- oxide. A solution of 3-bromo-4-nitropyridine 1-oxide (16 g, 73.06 mmol) in methanol (50 mL) was saturated with HCl gas and the reaction mixture was stirred at rt for 2 h. The reaction mixture was neutralized with NaHCC and concentrated. The concentrate was extracted with 5% MeOH in CH2CI2. The organic layer was separated, dried, filtered and concentrated to afford 12 g of the title product. XH NMR (300 MHz,CDCl3): δ 8.43 (s, 1H), 8.09-8.06 (d, J = 6.9 Hz, 1H), 7.36-7.28 (d, / = 7.2 Hz, 1H); MS (m/z): 210.12 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With pyridine; at 70℃; | General procedure: <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (10, 2g, 9.13mmol) was dissolved in pyridine (8mL) and the appropriate aniline (27.4mmol) was added to the solution (compound was directly dissolved in the aniline when it was a liquid). The resulting solution was heated at 70C under stirring for 16-72h. The solution was cooled on ice bath under stirring and ethanol (50mL) was added to the solution till precipitation of the desired compound, which was collected by filtration and washed with ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With pyridine; at 70℃; | General procedure: <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (10, 2g, 9.13mmol) was dissolved in pyridine (8mL) and the appropriate aniline (27.4mmol) was added to the solution (compound was directly dissolved in the aniline when it was a liquid). The resulting solution was heated at 70C under stirring for 16-72h. The solution was cooled on ice bath under stirring and ethanol (50mL) was added to the solution till precipitation of the desired compound, which was collected by filtration and washed with ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With pyridine; at 70℃; | General procedure: <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (10, 2g, 9.13mmol) was dissolved in pyridine (8mL) and the appropriate aniline (27.4mmol) was added to the solution (compound was directly dissolved in the aniline when it was a liquid). The resulting solution was heated at 70C under stirring for 16-72h. The solution was cooled on ice bath under stirring and ethanol (50mL) was added to the solution till precipitation of the desired compound, which was collected by filtration and washed with ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With pyridine; at 70℃; | General procedure: <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (10, 2g, 9.13mmol) was dissolved in pyridine (8mL) and the appropriate aniline (27.4mmol) was added to the solution (compound was directly dissolved in the aniline when it was a liquid). The resulting solution was heated at 70C under stirring for 16-72h. The solution was cooled on ice bath under stirring and ethanol (50mL) was added to the solution till precipitation of the desired compound, which was collected by filtration and washed with ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With pyridine; at 70℃; | General procedure: <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (10, 2g, 9.13mmol) was dissolved in pyridine (8mL) and the appropriate aniline (27.4mmol) was added to the solution (compound was directly dissolved in the aniline when it was a liquid). The resulting solution was heated at 70C under stirring for 16-72h. The solution was cooled on ice bath under stirring and ethanol (50mL) was added to the solution till precipitation of the desired compound, which was collected by filtration and washed with ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With pyridine; at 70℃; | General procedure: <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (10, 2g, 9.13mmol) was dissolved in pyridine (8mL) and the appropriate aniline (27.4mmol) was added to the solution (compound was directly dissolved in the aniline when it was a liquid). The resulting solution was heated at 70C under stirring for 16-72h. The solution was cooled on ice bath under stirring and ethanol (50mL) was added to the solution till precipitation of the desired compound, which was collected by filtration and washed with ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With pyridine; at 70℃; | General procedure: <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (10, 2g, 9.13mmol) was dissolved in pyridine (8mL) and the appropriate aniline (27.4mmol) was added to the solution (compound was directly dissolved in the aniline when it was a liquid). The resulting solution was heated at 70C under stirring for 16-72h. The solution was cooled on ice bath under stirring and ethanol (50mL) was added to the solution till precipitation of the desired compound, which was collected by filtration and washed with ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With pyridine; at 70℃; | General procedure: <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (10, 2g, 9.13mmol) was dissolved in pyridine (8mL) and the appropriate aniline (27.4mmol) was added to the solution (compound was directly dissolved in the aniline when it was a liquid). The resulting solution was heated at 70C under stirring for 16-72h. The solution was cooled on ice bath under stirring and ethanol (50mL) was added to the solution till precipitation of the desired compound, which was collected by filtration and washed with ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; at 70℃; | General procedure: <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (10, 2g, 9.13mmol) was dissolved in pyridine (8mL) and the appropriate aniline (27.4mmol) was added to the solution (compound was directly dissolved in the aniline when it was a liquid). The resulting solution was heated at 70C under stirring for 16-72h. The solution was cooled on ice bath under stirring and ethanol (50mL) was added to the solution till precipitation of the desired compound, which was collected by filtration and washed with ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With pyridine; at 70℃; | General procedure: <strong>[1678-49-5]3-Bromo-4-nitropyridine N-oxide</strong> (10, 2g, 9.13mmol) was dissolved in pyridine (8mL) and the appropriate aniline (27.4mmol) was added to the solution (compound was directly dissolved in the aniline when it was a liquid). The resulting solution was heated at 70C under stirring for 16-72h. The solution was cooled on ice bath under stirring and ethanol (50mL) was added to the solution till precipitation of the desired compound, which was collected by filtration and washed with ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In ethanol; for 17h;Reflux; | Preparation 8.1: 3-(4-(oxetan-3-yl)piperazin-l-yl)pyridin-4-amine 71 Step 1: l-(4-nitro-l-oxido-pyridin-l-ium-3-yl)-4-(oxetan-3-yl)piperazine [00278] A mixture of 3-bromo-4-nitro-l-oxido-pyridin-l-ium (500 mg, 2.283 mmol) and 1- (oxetan-3-yl)piperazine (649.3 mg, 4.566 mmol) in EtOH (10 mL) were heated at reflux for 17 hours. The reaction was cooled to ambient temperature and the solvent removed in vacuo. The residue was passed through a 25 g SCX-2 cartridge (pre-wetted with MeOH), eluting with 2M H3 in MeOH/DCM. The solvents were removed in vacuo and the residue purified by column chromatography (ISCO Companion, 40 g column, eluting with 0 to 10% MeOH/DCM, loaded in DCM) to give l-(4-nitro-l-oxido-pyridin-l-ium-3-yl)-4-(oxetan-3- yl)piperazine as an orange solid (553 mg, 86% Yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Intermediate 2 3-(benzylthio)-4-nitropyridine 1-oxide [0121] NaH (60% on mineral oil, 276 mg, 6.9 mmol) in dioxane (25 ml) was added phenylmethanethiol (0.73 ml, 6.3 mmol), after stirred at room temperature for 2 hours, 3-bromo-4-nitropyridine 1-oxide (1.1 g, 5.0 mmol) was added. The mixture was stirred for 3 days, acidified with 1M HCl, extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (10-100% EtOAc in hexane) to yield Intermediate 2 (688 mg, 53%). [0123] 1H NMR (METHANOL-d4) δ 8.41 (d, J=1.8 Hz, 1H), 8.24 (d, J=7.3 Hz, 1H), 8.10-8.13 (m, 1H), 7.47 (d, J=7.3 Hz, 2H), 7.37 (t, J=7.6 Hz, 2H), 7.29-7.33 (m, 1H), 4.37 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [18F]-tetrabutylammonium fluoride; In dimethyl sulfoxide; at 25℃; for 0.25h; | Example 6 (0057) Radiochemical synthesis of [18F]-3-fluoro-4-nitropyridine N-oxide ([18F]-9) from 3-bromo-4-nitropyridine N-oxide (8): 100 μL of 3-bromo-4-nitropyridine N-oxide (8) dissolved in DMSO (20 mg/mL) were added to 100 μL of [18F]-TBAF solution (10 mCi, 370 MBq) in 3 mL microreactor vial and allowed to react for 15 min. 100 μL of this solution with or without reference standard (20 μg) were injected into a semiprep C-18 HPLC column equipped with a variable wavelength UV-Vis detector and a radiation detector (conditions C). The radioactive peaks were collected and the radioactivity of each fraction measured using a Capintec dose calibrator. The radiochemical yield was calculated as radioactivity in the peak corrected for decay over radioactivity injected. Example 7 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With tetrabutyl ammonium fluoride; In tetrahydrofuran; dimethyl sulfoxide; at 125℃; | Example 3 (0054) Non-radioactive fluorination of 3-bromo-4-nitropyridine N-oxide (8): 10 muL of 1 M TBAF solution in THF (10 mumol, 0.5 eq.) was added to a solution of a 3-bromo-4-nitropyridine N-oxide (98+%, Alfa Aesar) (20 mumol, 1 eq.) in 500 muL of anhydrous DMSO in a 2 mL HPLC vial. The reaction was analyzed by HPLC (conditions B). Retention times: 3-bromo-4-nitropyridine N-oxide (8)=11.84 min, 3-fluoro-4-nitropyridine N-oxide (9)=7.93 min. Retention time for the product matched within 0.05 min the reference standard. Identity of the product was confirmed by HR-MS (m/z M+ exp.: 158.0141, calc.: 158.0128) and 1H, 13C and 19F NMR. Product amount was calculated from the area under the curve of the HPLC UV2 trace using a calibration curve. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | In propan-1-ol; at 90℃; for 5h; | In a round bottom flask fitted with magnetic stirrer and reflux condenser, 3- bromo-4-nitro-pyridine 1 -oxide (5.3 g, 24.25 mmol) and <strong>[93919-56-3]4-(trifluoromethoxy)benzylamine</strong> (9.28 g, 48.55 mmol) were dissolved in propanol (50 ml) and heated to 90 C for 5 hours. Reaction mixture was allowed to cool overnight whilst stirring, with a solid crashing out of the reaction crude. This solid was filtered off, washed with I PA (2 x 10 ml) and dried in vacuo to afford the title compound (4.64 g, 58%). [00294] LCMS Method: 2, RT: 6.50 min, Ml: 330 [M+1] [00295] NMR, Method 1 : (DMSO) 8.82 (t 1 H), 8.05 (d 1 H), 7.94 (d 1 H), 7.52 (d 2H), 7.49 (dd 1 H), 7.36 (d 2H), 4.68 (d 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With triethylamine; In tetrahydrofuran; at 60℃; for 8h; | Add L-2-(2,6-diisopropylbenzamide)pyrrolidine to a 100 mL flask(5.48g, 20mmol), triethylamine(27.7 mL, 200 mmol, 10 eq),3-bromo 4-nitropyridine oxynitride (5.45 g, 25 mmol, 1.25 eq)Tetrahydrofuran(35mL), stir at 60 C overnight,The crude product is obtained by column chromatography to obtain a bright yellow solid.7.83g,Yield is 95%,>99% ee. |
Tags: 1678-49-5 synthesis path| 1678-49-5 SDS| 1678-49-5 COA| 1678-49-5 purity| 1678-49-5 application| 1678-49-5 NMR| 1678-49-5 COA| 1678-49-5 structure
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