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CAS No. : | 341-92-4 | MDL No. : | MFCD00156398 |
Formula : | C10H6FNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 191.16 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 52.73 |
TPSA : | 45.82 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.44 cm/s |
Log Po/w (iLOGP) : | 1.74 |
Log Po/w (XLOGP3) : | 2.85 |
Log Po/w (WLOGP) : | 3.31 |
Log Po/w (MLOGP) : | 3.17 |
Log Po/w (SILICOS-IT) : | 1.16 |
Consensus Log Po/w : | 2.44 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.28 |
Solubility : | 0.0996 mg/ml ; 0.000521 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.47 |
Solubility : | 0.0646 mg/ml ; 0.000338 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.74 |
Solubility : | 0.0351 mg/ml ; 0.000184 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.8 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
palladium on activated charcoal; In ethyl acetate; | 4-Fluoro-1-aminoaphthalene <strong>[341-92-4]4-Fluoro-1-nitro-naphthalene</strong> (1 g) was dissolved in EtOAc (20 mL) and placed into a hydrogenating flask containing Palladium on activated charcoal (10%, 0.3 g). The reaction mixture was hydrogenated at 50 psi for 5 hr. During the reaction, the pressure of the hydrogen dropped due to the consuming of the hydrogen, and it was brought back to 50 psi a few times. Finally, the reaction stopped when all the starting material was used. The resulting solution was filtered through a pad of celite and washed with EtOAc (20 mL). The clear filtrate was concentrated and dried under vacuum to yield 4-Fluoro-1-aminonaphthalene. TLC (SiO2, CH2 Cl2): Rf =0.33. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In xylenes; for 1h;Heating / reflux; | The nitronaphthalene diazonium tetrafluoroborate salt from above (3.448 g, 12.0 mmol" 1 equiv. ) was suspended in 100 mL xylenes and heated to reflux for 1 h, then allowed to cool back to room temperature. Water was then added and the product extracted twice with ether. The combined extracts were dried [(MGS04),] filtered, and the solvents were removed in vacuo. The product [4-FLUORO-L-NITRONAPHTHALENE] was purified by column chromatography on silica gel using 10% EtOAc in hexanes as eluent providing 1.95 g of 4-fluoro-1-nitro-naphthalene (10.20 mmol, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In N,N-dimethyl acetamide; at 90℃; for 0.5h; | INTERMEDIATE 1 (125 mg, 0.50 mmol) was combined with 4-fluoronitronaphthalene (95 mg, 0.5 mmol) and Cs2CO3 (1.0 g, 3 mmol) in 5 mL of N,N-dimethylacetamide. The reaction mixture was stirred at 90 0C for 30 min., then was dumped into water and acidified with 2N aq. HCl to pH <2. The resulting solid precipitate was extracted with ethyl acetate and washed with water followed by brine, dried over anhydrous Na2SO4, filtered, and concentrated. Purification by Combi-Flash (silica, 5-30% ethyl acetate/hexane gradient) gave the product. LC-MS calc. for C22H16N2O5S: 420; Found: 421 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The nitronaphthalene diazonium tetrafluoroborate salt from above (3.448 g, 12.0 mmol, 1 equiv.) was suspended in 100 mL xylenes, heated to reflux for 1 h, then allowed to cool back to room temperature. Water was then added and the product extracted twice with ether. The combined extracts were dried (MgSO4), filtered, and the solvents were removed in vacuo. The crude product was purified by column chromatography on SiO2 using 10% EtOAc in hexanes as eluent, providing 1.95 g of 4-fluoro-1-nitronaphthalene (10.20 mmol, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium formate; sodium t-butanolate;palladium; In dimethyl sulfoxide; ethyl acetate; | The diazonium salt from above (408 mg, 1.42 mmol, 1 equiv.) was mixed with silica gel (63-200 micron, 2500 mg) and rendered homogeneous by light mixing in a mortar. This mixture was placed in a round bottom flask equipped with a mechanical stirrer and a condenser, and heated to 150-170 C. for 0.5 h. The mixture turned dark. The solid mixture was allowed to cool back to room temperature, placed on top of a short plug of silica gel, the transfer being aided by some hexanes solvent. The pure <strong>[341-92-4]4-fluoro-1-nitronaphthalene</strong> product was eluted with 10% EtOAc in hexanes. After removal of the solvents in vacuo 190 mg of product (0.99 mmol, 70% yield) was collected as a yellow-orange solid. 2-Isopropyl-6-methyl-4-pyrimidinol (264 mg, 1.74 mmol, 1.1 equiv.) was dissolved in 2.5 mL anhydrous DMSO. Sodium tert-butoxide (159 mg, 1.66 mmol, 1.05 equiv.) was added in one portion and the mixture was left stirring for 15 min at room temperature. Solid <strong>[341-92-4]4-fluoro-1-nitro-naphthalene</strong> was then added in one portion and the mixture was gently heated to 60 C. while stirring for 4 h. A color change from orange to green was noted. Saturated aqueous sodium bicarbonate solution was then added and the product extracted 3 times with EtOAc. The combined organic extracts were washed once with water and with brine, dried (Na2SO4) and filtered. The volatiles were removed in vacuo to afford a waxy orange solid. Crude yield was 459 mg (1.42 mmol or 90%). The material was used without purification for the next step. The crude nitronaphthyl-pyrimidinyl ether from above (459 mg, 1.42 mmol, 1 equiv.) was taken up in 35 mL EtOAc and 35 mL EtOH. Ammonium formate was added (537 mg, 8.52 mmol, 6 equiv.) as well as 400 mg of 10% palladium-on-carbon. The reaction mixture was heated to a gentle reflux for one h, cooled back to room temperature, filtered through diatomaceous earth and the volatiles were removed in vacuo. The crude product was purified by chromatography on SiO2, eluding with 20-40% EtOAc in hexanes. The desired aminonaphthyl-pyrimidinyl ether was isolated as a yellow foam (176 mg, 0.6 mmol, 42% for 2 steps). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium tert-butylate; In dimethyl sulfoxide; ethyl acetate; | Example 6 Synthesis of 7-(4-amino-naphthalen-1-yl)-7H-purine (6a) and 9-(4-amino-naphthalen-1-yl)-9H-purine (6b) Purine (137 mg, 1.14 mmol, 1 equiv.) in 2.0 mL anhydrous DMSO was treated with potassium tert-butoxide (128 mg, 1.14 mmol, 1 equiv.) at room temperature. When the solution was completely homogeneous, <strong>[341-92-4]4-fluoro-1-nitro-naphthalene</strong> (137 mg, 1.14 mmol, 1 equiv.) was added in one portion and the mixture was heated to 60 C. for 15 min. The reaction was allowed to cool, quenched with dilute aqueous NaHCO3 solution (50 mL) and the product was collected by filtration to afford approximately a 4:1 ratio of regioisomers favoring 7-(4-nitro-naphthalen-1-yl)-7H-purine over 9-(4-nitro-naphthalen-1-yl)-9H-purine. These regioisomers were separated at this stage by column chromatography on SiO2 using hexanes/EtOAc eluent mixtures, the major isomer eluding at lower Rf. Reductions to form 6a and 6b and couplings to form ureas were performed by procedures analogous to those described in Examples above. Other substituted purines (for example 3-chloro-purine) can be reacted in an analogous fashion and functionalized further to introduce for example 3-thioalkyl, 3-alkoxy, 3-alkyl or aryl, 3-alkyl- or aryl-amino groups on the purine moiety. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With potassium carbonate; In N,N-dimethyl-formamide; | Example 10 Synthesis of 4-(4-amino-naphthalen-1-yloxy)-pyridine-2-carboxylic acid methyl ester To a solution of <strong>[341-92-4]1-fluoro-4-nitro-naphthalene</strong> (1.0 g, 5.24 mmol) in dry DMF (22 mL) was added 4-hydroxy-pyridine-2-carboxylic acid methyl ester (0.993 g, 5.24 mmol) and K2CO3 (7.24 g, 52.4 mmol). The resulting yellow suspension was stirred at 100 C. under argon for five h. After cooling to room temperature, the solution was diluted with CH2Cl2 (62 mL) and 10% Pd/C (1 g) was added. The suspension was stirred under a H2 balloon for 72 h. The reaction was then filtered through a plug of diatomaceous earth and rinsed with EtOAc (150 mL) and extracted with H2O (3*100 mL), brine (1*100 mL) and dried over MgSO4. The solvent was removed via rotary evaporation and the resulting oil was applied to a flash silica column eluding with MeOH:CH2Cl2 (2:98) to provide the title compound (800 mg, 52%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In ethyl acetate; N,N-dimethyl-formamide; | Method C-c tert-Butyl [1-(4-aminonaphthalen-1-yl)pyrrolidin-3-yl]methylcarbamate tert-Butyl methylpyrrolidin-3-ylcarbamate (1.86 g) was slowly added to a suspension of <strong>[341-92-4]4-fluoro-1-nitronaphthalene</strong> (1.91 g) and potassium carbonate (2.8 g) in DMF (10 ml). After 10 minutes, ethyl acetate (50 ml) was added, and the mixture was washed with water (3*50 ml) in a separating funnel, dried with sodium sulfate, filtered and concentrated. The substance was then treated as described for method B. This resulted in the product with the molecular weight of 341.46 (C20H27N3O2); MS (ESI): 342 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | 4-(4-Nitronaphthalen-1 -yloxy)pyridin-2 -amineTo a stirred suspension of 2-aminopyridin-4-ol (53.9 g, 489 mmol) in acetonitrile (500 ml.) was added DBU (102 ml_, 678 mmol) dropwise over 30 min. The resulting solution was stirred at RT for 30 min and was then treated dropwise with a solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (72.0 g, 377 mmol) in acetonitrile (400 ml.) over 50 min. After stirring overnight at RT the reaction was heated at 500C for 2 hr. The reaction was removed from the heat, but not cooled and with stirring, treated with water (6 x 100 ml_). The mixture was allowed to cool to RT over 2 hr and was then cooled further to O0C. The yellow precipitate was collected by filtration and washed sequentially with a mixture of water and acetonitrile (1 :1 , 2 x 100 ml.) and then with water (500 ml.) to give the title compound as a yellow solid (76.0 g, 70%): m/z 283 (M+H)+ (ES+). | |
70% | To a stirred suspension of 2-aminopyridin-4-ol (53.9 g, 489 mmol) in MeCN (500 mL) was added DBU (102 mL, 678 mmol) dropwise over 30 min. The resulting solution was maintained at RT for 30 min and was then treated dropwise with a solution of 1 -fluoro-4- nitronaphthalene (72.0 g, 377 mmol) in acetonitrile (400 mL) over 50 min. After stirring overnight at RT the reaction was heated at 50C for 2 hr. The reaction was removed from the heat, and with stirring, was diluted with water (600 mL) portionwise to minimise the risk of rapid crystallization. The mixture was allowed to cool to RT over 2 hr and was then cooled further to 0C. The yellow precipitate so produced was collected by filtration and washed sequentially with a mixture of water and acetonitrile (1 :1 , 2 x 100 mL) and then with water (500 mL) to give 4-(4-nitronaphthalen-1 -yloxy)pyridin-2-amine, as a yellow solid (76.0 g, 70%): m/z 283 (M+H)+ (ES+). | |
70% | To a stirred suspension of 2-aminopyridin-4-ol (53.9 g, 489 mmol) in MeCN (500 mL) was added DBU (102 mL, 678 mmol) dropwise over 30 min. The resulting solution was maintained at RT for 30 min and was then treated dropwise with a solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (72.0 g, 377 mmol) in acetonitrile (400 mL) over 50 min. After stirring overnight at RT the reaction was heated at 50 C. for 2 hr. The reaction was removed from the heat, and with stirring, was diluted with water (600 mL) portionwise to minimise the risk of rapid crystallization. The mixture was allowed to cool to RT over 2 hr and was then cooled further to 0 C. The yellow precipitate so produced was collected by filtration and washed sequentially with a mixture of water and acetonitrile (1:1, 2×100 mL) and then with water (500 mL) to give 4-(4-nitronaphthalen-1-yloxy)pyridin-2-amine, as a yellow solid (76.0 g, 70%): m/z 283 (M+H)+ (ES+). |
70% | To a stirred suspension of 2-aminopyridin-4-ol (53.9 g, 489 mmol) in MeCN (500 mL) was added DBU (102 mL. 678 mmol) dropwise over 30 min. The resulting solution was maintained at RT for 30 min and was then treated dropwise with a solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (72.0 g, 377 mmol) in acetonitrile (400 mL) over 50 min. The reaction mixture was stirred overnight at RT and was then heated to 50 C. for 2 hr. The heating was removed and the stirred mixture was diluted cautiously with water (600 mL) after which it was allowed to cool to RT over 2 hr and was then cooled further to 0 C. The yellow precipitate so produced was collected by filtration and was washed sequentially with a mixture of water and acetonitrile (1:1, 2×100 mL) and then with water (500 mL) to give the 4-(4-nitronaphthalen-1-yloxy)pyridin-2-amine (77), as a yellow solid (76.0 g, 70%): m/z 283 (M+H)+ (ES+). | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; acetonitrile; | Example 60 (R)-N-(4-(4-(3-(3-tert-Butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)pyridin-2-yl)-3-(dimethylamino)pyrrolidine-1-carboxamide To a stirred suspension of 2-aminopyridin-4-ol (53.9 g, 489 mmol) in MeCN (500 mL) was added DBU (102 mL, 678 mmol) dropwise over 30 min. The resulting solution was maintained at RT for 30 min and was then treated dropwise with a solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (72.0 g, 377 mmol) in acetonitrile (400 mL) over 50 min. The reaction mixture was stirred overnight at RT and was then heated to 50 C. for 2 hr. The heating was removed and the stirred mixture was diluted cautiously with water (600 mL) after which it was allowed to cool to RT over 2 hr and was then cooled further to 0 C. The yellow precipitate so produced was collected by filtration and was washed sequentially with a mixture of water and acetonitrile (1:1, 2*100 mL) and then with water (500 mL) to give the 4-(4-nitronaphthalen-1-yloxy)pyridin-2-amine (77), as a yellow solid (76.0 g, 70%): m/z 283 (M+H)+ (ES+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16.48% | To a solution of 6-aminopyrimidin-4(3/-/)-one (866 mg, 7.79 mmol) in DMSO (10.0 ml.) at RT was added DBU (1.29 ml_, 8.57 mmol) and after 30 min a sol ution of 1-fluoro-4- nitronaphthalene (1.57 g, 8.18 mmol) in DMSO (3.0 ml.) was added over 2 min. The resulting mixture was maintained at RT for 2 hr and was diluted with MeOH (20 ml.) and TFA (2.0 ml.) was added. The solution was subjected to SCX capture and release and the crude product so obtained was purified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 50- 100%, gradient elution) to afford the title compound as a yellow solid (370mg, 16.48 %); R' 3.82 min (Method 1 basic); m/z 283 (M+H)+ (ES+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | A suspension of sodium hydrogensulfide (1 .53 g, 18.6 mmol) in NMP (8.0 mL) was purged with N2, and was added dropwise to a similarly purged solution of 2-chloro-4-fluoropyridine (1.74 g, 13.3 mmol) in NMP (6.0 mL) over 1 hr. The reaction mixture was kept at RT for 1 hr and then treated dropwise with a solution of 1 -fluoro-4-nitronaphthalene (3.80 g, 19.9 mmol) and DIPEA (4.6 mL, 27 mmol) in NMP (10 mL) over 5 min. After a further 1 hr at RT MeOH (5.0 mL) was added and the reaction mixture kept at RT for 48 hr. The resulting mixture was diluted with EtOAc (250 mL) and was washed sequentially with 2M aq. NaOH (2 x 150 mL), saturated aq. NaHC03 (150 mL), water (150 mL) and brine (2 x 150 mL) The organic layer was dried and evaporated in vacuo and the residue was purified by flash column chromatography (S1O2, 120 g, EtOAc in isohexane, 10-30%, gradient elution) to afford 2- chloro-4-(4-nitronaphthalen-1 -ylthio)pyridine as a yellow oil (1.95g, 5.66 mmol, 43%); R1 5.02 min (Method 1 basic); m/z 317 (M+H)+ (ES+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Intermediate BTo a solution of ethyl 2-(2-(fe/f-butoxycarbonylamino)pyridin-4-yl)acetate (WO 2007089512) (10.0 g, 35.7 mmol) under N2 in THF (100 mL), at -78C, was added a solution of DIBAL in THF (1 .0M, 71 .0 mL, 71 .0 mmol) over 1 hr. The reaction mixture was stirred at -78 to -60C for 40 min and was then warmed to -15C over 1 hr. The solution was re-cooled to -78C and was treated with a further aliquot of DIBAL solution (36.0 mL, 36.0 mmol) and was allowed to warm to -40C and stirred for 1 hr. The reaction was quenched by the cautious addition of water (10 mL), followed MgS04. The solids were removed by filtration and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography (Si02, 330 g, EtOAc in hexanes, 65% v/v, isocratic elution) to give ferf-butyl 4-(2-hydroxyethyl)pyridin-2- ylcarbamate, (6.0 g, 64%) as a yellow solid: m/z 239 (M+H)+ (ES+).To a solution of ferf-butyl 4-(2-hydroxyethyl)pyridin-2-ylcarbamate (6.0 g, 25 mmol) in THF (70 mL) at 0C was added sodium hydride (2.52 g, 60% wt dispersion in mineral oil, 63.0 mmol) and the bright yellow suspension stirred for 20 min and then treated with 1 -fluoro-4- nitronaphthalene (4.81 g, 25.2 mmol) in a single portion. After stirring at RT for 2 hr the mixture was treated with water (100 mL) followed by EtOAc (100 mL) and the solid which formed at the interface was collected by filtration. The organic phase was separated and was washed with saturated aq. NaHC03 and brine and was then dried and evaporated in vacuo to furnish an orange solid. The two solids were combined and triturated with MeOH (50 mL) to provide ferf- butyl 4-(2-(4-nitronaphthalen-1 -yloxy)ethyl)pyridin-2-ylcarbamate, as a yellow solid (1 1 .0 g, 98%): m/z 410 (M+H)+ (ES+). To a suspension of ferf-butyl 4-(2-(4-nitronaphthalen-1 -yloxy)ethyl)pyridin-2-ylcarbamate (900 mg, 2.20 mmol) in DCM (10.0 mL) was added TFA (10.0 mL) and the reaction mixture was stirred at RT overnight. The resulting mixture was evaporated in vacuo and the residue subjected to SCX capture and release. The crude product so obtained was taken up into THF (8.0 mL) and DIPEA (660 muIota, 3.8 mmol) and then acetyl chloride (147 muIota, 2.06 mmol) were added. After stirring for 1 hr, the mixture was diluted with saturated aq. NaHC03 (10.0 mL) and was extracted with EtOAc (2 x 20 mL). The combined organic layers were washed with brine and then dried, and evaporated in vacuo. The residue was taken up in a mixture of acetonitrile and a solution of NH3 in MeOH (7M, 1 :1 v/v, 20 mL) and after 10 min was re-evaporated in vacuo. The residue was triturated with MeOH (10.0 mL) to afford W-(4-(2-(4-nitronaphthalen- 1 -yloxy)ethyl)pyridin-2-yl)acetamide, as a yellow solid (570 mg, 74%): m/z 352 (M+H)+ (ES+).A solution of /V-(4-(2-(4-nitronaphthalen-1 -yloxy)ethyl)pyridin-2-yl)acetamide (570 mg, 1.62 mmol) in a mixture of AcOH: MeOH (6:1 v/v, 54 mL) was subjected to hydrogenation by passage through a Thales H-cube (1 mLmin"1, 30 mm, 10% Pt/C Cat-Cart, full H2, 45C). The solvent was removed by evaporation in vacuo, and, the residue was subjected to SCX capture and release to furnish the title compound, Intermediate B, (550 mg, 100%): m/z 322 (M+H)+ (ES+). | |
98% | To a solution of tert-butyl 4-(2-hydroxyethyl)pyridin-2-ylcarbamate (20) (6.00 g, 25.2 mmol) in THF (70 mL) was added sodium hydride (2.52 g, 63.0 mmol, 60 wt %) at 0 C. The bright yellow suspension was stirred for 20 min at 0 C. and the <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (4.81 g, 25.2 mmol) added in a single portion. After stirring at RT for 2 hr, water (100 mL) was added followed by EtOAc (100 mL). The solid formed between the layers was collected by filtration and the organic phase was washed with saturated aq NaHCO3 solution (100 mL), brine (100 mL) and dried. The volatiles were removed to give an orange solid. The solids were combined and triturated from MeOH (50 mL) to give tert-butyl 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate (21) as a yellow solid (11.0 g, 98%): m/z 410 (M+H)+ (ES+). | |
With sodium hydride; In tetrahydrofuran; methanol; water; ethyl acetate; | To a solution of tert-butyl 4-(2-hydroxyethyl)pyridin-2-ylcarbamate (20) (6.00 g, 25.2 mmol) in THF (70 mL) was added sodium hydride (2.52 g, 63.0 mmol, 60 wt %) at 0 C. The bright yellow suspension was stirred for 20 min at 0 C. and the <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (4.81 g, 25.2 mmol) added in a single portion. After stirring at RT for 2 hr, water (100 mL) was added followed by EtOAc (100 mL). The solid formed between the layers was collected by filtration and the organic phase was washed with saturated aq NaHCO3 solution (100 mL), brine (100 mL) and dried. The volatiles were removed to give an orange solid. The solids were combined and triturated from MeOH (50 mL) to give tert-butyl 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate (21) as a yellow solid (11.0 g, 98%): m/z 410 (M+H)+ (ES+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride;SiO2; In 2-Methylpentane; water; ethyl acetate; N,N-dimethyl-formamide; | To a stirred solution of (40) (1.55 g, 10.0 mmol) in DMF (30 mL), under nitrogen at 0 C., was added sodium hydride (60% wt, 0.61 g, 15.0 mmol) and the resulting mixture was stirred at 0 C. for 5 min. A solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (1.95 g, 10 mmol) in DMF (30 mL) was added dropwise and the resulting dark-red mixture was stirred at 0 C. for a further 5 min and then at RT for 2 hr. The reaction mixture was quenched by the addition of saturated aq NH4Cl solution (10 mL). Water (150 mL) and EtOAc (150 mL) were added, and the layers were separated. The aq layer was extracted with EtOAc (3*100 mL) and the combined organic extracts were washed with brine, dried (MgSO4) and evaporated in vacuo. The crude residue was purified by flash column chromatography (SiO2, 80 g, 0-60% EtOAc in isohexane, gradient elution) to afford 4-(2-(4-nitronaphthalen-1-yloxy)propan-2-yl)pyridin-2-amine (41) (282 mg, 8%) as a red oil: m/z 324 (M+H)+ (ES+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | To a stirred solution of (37) (73 mg, 0.528 mmol) in DMF (1.5 mL), under nitrogen at 0 C., was added sodium hydride (32 mg, 0.793 mmol, 60 wt %). The resulting mixture was stirred at 0 C. for 40 min, and a solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (101 mg, 0.528 mmol) in DMF (1.5 mL) was added dropwise. The resulting dark-red mixture was stirred at 0 C. for 5 min and at RT for 40 min and was quenched by the addition of 1.0 mL of NH4Cl solution. Water (20 mL) and EtOAc (20 mL) were added, and the layers were separated. The aqueous layer was extracted with EtOAc (3×15 mL). The combined organic extracts were washed with brine, dried and the solvents removed in vacuo. The crude material was purified by column chromatography (SiO2, 12 g, 0-80% EtOAc in isohexane, gradient elution) to give 4-(1-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-amine (38) (94.6 mg, 57%) as an orange gum: m/z 310 (M+H)+ (ES+). | |
With sodium hydride; ammonium chloride;SiO2; In 2-Methylpentane; water; ethyl acetate; N,N-dimethyl-formamide; | To a stirred solution of (37) (73 mg, 0.528 mmol) in DMF (1.5 mL), under nitrogen at 0 C., was added sodium hydride (32 mg, 0.793 mmol, 60 wt %). The resulting mixture was stirred at 0 C. for 40 min, and a solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (101 mg, 0.528 mmol) in DMF (1.5 mL) was added dropwise. The resulting dark-red mixture was stirred at 0 C. for 5 min and at RT for 40 min and was quenched by the addition of 1.0 mL of NH4Cl solution. Water (20 mL) and EtOAc (20 mL) were added, and the layers were separated. The aqueous layer was extracted with EtOAc (3*15 mL). The combined organic extracts were washed with brine, dried and the solvents removed in vacuo. The crude material was purified by column chromatography (SiO2, 12 g, 0-80% EtOAc in isohexane, gradient elution) to give 4-(1-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-amine (38) (94.6 mg, 57%) as an orange gum: m/z 310 (M+H)+ (ES+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Sodium hydride (119 mg, 2.97 mmol) was added to a stirred solution of (47) (250 mg, 0.991 mmol) in DMF (6.0 mL) at 0 C., under nitrogen and after 45 min a solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (189 mg, 0.991 mmol) in DMF (6.0 mL) was added dropwise, over 2 min. The resulting dark-brown reaction mixture was stirred at 0 C. for 5 min, and was then warmed to RT. After 70 min. a saturated aq solution of NH4Cl (3.0 mL) was added and the mixture was partitioned between water and EtOAc. The aq layer was extracted twice with EtOAc and the combined organic extracts were washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g; 0-70% EtOAc in isohexane, gradient elution) to afford tert-butyl 4-(2-(4-nitronaphthalen-1-yloxy)propyl)pyridin-2-ylcarbamate (48) (293 mg, 65%) as an orange foam: m/z 424.0 (M+H)+ (ES+). | |
With sodium hydride; ammonium chloride;SiO2; In 2-Methylpentane; ethyl acetate; N,N-dimethyl-formamide; | Sodium hydride (119 mg, 2.97 mmol) was added to a stirred solution of (47) (250 mg, 0.991 mmol) in DMF (6.0 mL) at 0 C., under nitrogen and after 45 min a solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (189 mg, 0.991 mmol) in DMF (6.0 mL) was added dropwise, over 2 min. The resulting dark-brown reaction mixture was stirred at 0 C. for 5 min, and was then warmed to RT. After 70 min, a saturated aq solution of NH4Cl (3.0 mL) was added and the mixture was partitioned between water and EtOAc. The aq layer was extracted twice with EtOAc and the combined organic extracts were washed with brine, dried (MgSO4) and evaporated in vacuo The residue was purified by flash column chromatography (SiO2, 40 g; 0-70% EtOAc in isohexane, gradient elution) to afford tert-butyl 4-(2-(4-nitronaphthalen-1-yloxy)propyl)pyridin-2-ylcarbamate (48) (293 mg, 65%) as an orange foam: m/z 424.0 (M+H)+ (ES+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | To a solution of the alcohol (53) (0.62 g, 2.46 mmol) in DMF (4.0 mL) was added sodium hydride (60% dispersion in mineral oil, 0.246 g, 6.14 mmol) in a single portion and the mixture sonicated under a flow of nitrogen and then stirred at RT for 30 min. The resulting yellow suspension was cooled to 0 C. and a solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (470 mg, 2.46 mmol) in DMF (2.0 mL) was added over 10 min. The reaction mixture was warmed to RT and glacial acetic (1.0 mL) was added. The mixture was poured onto saturated aq NaHCO3 solution and extracted with EtOAc. The organic layer was washed with saturated aq Na2CO3, solution, three times with water and twice with brine then dried (MgSO4) and evaporated in vacuo to give a yellow solid. The solid was suspended in MeOH (20 mL) and sonicated and the insoluble residue was collected by filtration and was washed with MeOH (10 mL) and then ether to afford tert-butyl 4-(1-(4-nitronaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate (54) as an off white solid (0.73 g, 67%): m/z 424 (M+H)+ (ES+). | |
With sodium hydride; nitrogen; In methanol; N,N-dimethyl-formamide; mineral oil; | To a solution of the alcohol (53) (0.62 g, 2.46 mmol) in DMF (4.0 mL) was added sodium hydride (60% dispersion in mineral oil, 0.246 g, 6.14 mmol) in a single portion and the mixture sonicated under a flow of nitrogen and then stirred at RT for 30 min. The resulting yellow suspension was cooled to 0 C. and a solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (470 mg, 2.46 mmol) in DMF (2.0 mL) was added over 10 min. The reaction mixture was warmed to RT and glacial acetic (1.0 mL) was added. The mixture was poured onto saturated aq NaHCO3 solution and extracted with EtOAc. The organic layer was washed with saturated aq Na2CO3, solution, three times with water and twice with brine then dried (MgSO4) and evaporated in vacuo to give a yellow solid. The solid was suspended in MeOH (20 mL) and sonicated and the insoluble residue was collected by filtration and was washed with MeOH (10 mL) and then ether to afford tert-butyl 4-(1-(4-nitronaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate (54) as an off white solid (0.73 g, 67%): m/z 424 (M+H)+ (ES+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | To a stirred solution of the alcohol (59) (1.11 g, 4.17 mmol) in DMF (10.0 mL) at 0 C. under nitrogen was added sodium hydride (350 mg, 8.75 mmol) in a single portion. The mixture was warmed to RT for 30 min and was then sonicated, flushed with nitrogen and re-cooled to 0 C. A solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (797 mg, 4.17 mmol) in DMF (4.0 mL) was added over 5 min and the reaction mixture allowed to warm to RT and after 30 min glacial acetic acid (1.0 mL) was added. The reaction mixture was poured onto saturated aq NaHCO3 solution and extracted twice with EtOAc. The combined organic extracts were washed three times with water and with brine and then dried (MgSO4), and evaporated in vacuo. The residue was triturated from EtOAc and washed with ether (20 mL) to afford tert-butyl 4-(2-methyl-1-(4-nitronaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate (60) as a yellow solid (1.23 g, 64%): m/z 438 (M+H)+ (ES+). | |
With sodium hydride; In acetic acid; ethyl acetate; N,N-dimethyl-formamide; | To a stirred solution of the alcohol (59) (1.11 g, 4.17 mmol) in DMF (10.0 mL) at 0 C. under nitrogen was added sodium hydride (350 mg, 8.75 mmol) in a single portion. The mixture was warmed to RT for 30 min and was then sonicated, flushed with nitrogen and re-cooled to 0 C. A solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (797 mg, 4.17 mmol) in DMF (4.0 mL) was added over 5 min and the reaction mixture allowed to warm to RT and after 30 min glacial acetic acid (1.0 mL) was added. The reaction mixture was poured onto saturated aq NaHCO3 solution and extracted twice with EtOAc. The combined organic extracts were washed three times with water and with brine and then dried (MgSO4), and evaporated in vacuo. The residue was triturated from EtOAc and washed with ether (20 mL) to afford tert-butyl 4-(2-methyl-1-(4-nitronaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate (60) as a yellow solid (1.23 g, 64%): m/z 438 (M+H)+ (ES+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | To a stirred solution of (40) (1.55 g, 10.0 mmol) in DMF (30 mL), under nitrogen at 0 C., was added sodium hydride (60% wt, 0.61 g, 15.0 mmol) and the resulting mixture was stirred at 0 C. for 5 min., A solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (14) (1.95 g, 10 mmol) in DMF (30 mL) was added dropwise and the resulting dark-red mixture was stirred at 0 C. for a further 5 min and then at RT for 2 hr. The reaction mixture was quenched by the addition of saturated aq NH4Cl solution (10 mL). Water (150 mL) and EtOAc (150 mL) were added, and the layers were separated. The aq layer was extracted with EtOAc (3×100 mL) and the combined organic extracts were washed with brine, dried (MgSO4) and evaporated in vacuo. The crude residue was purified by flash column chromatography (SiO2, 80 g, 0-60% EtOAc in isohexane, gradient elution) to afford 4-(2-(4-nitronaphthalen-1-yloxy)propan-2-yl)pyridin-2-amine (41) (282 mg, 8%) as a red oil: m/z 324 (M+H)+ (ES+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine hydrate; In isopropyl alcohol; at 60℃; for 2h; | A. (4-nitronaphthalen-1-yl)hydrazine, 132a A solution of <strong>[341-92-4]1-fluoro-4-nitronaphthalene</strong> (670 mg, 3.51 mmol) in iPrOH (20 mL) was added N2H4.H2O (460 mg, 9.19 mmol) and heated to 60 C. for 2 hrs. After cooled to RT, the solid was collected, washed with H2O (5 mL) and EtOH (5 mL), and then dried under vacuo to give product as a yellowish solid (500 mg, 70.2%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With dipotassium peroxodisulfate; bismuth (III) nitrate pentahydrate; In acetonitrile; at 130℃; for 24h;Sealed tube; | General procedure: An oven dried resealable screw cap standard reaction tube containinga magnetic stir bar was charged with potassium persulfate(1.75 mmol, 472.5 mg), bismuth nitrate (1.0 mmol, 486 mg). Thenaryl carboxylic (0.5 mmol) was introduced in this mixture followedby acetonitrile (3 mL) was added in it. The tube was placed in apreheated oil bath at 130 C and the reaction mixture was stirredvigorously for 24 h in air atmosphere. The reaction mixture wascooled to room temperature, diluted with 2 mL ethyl acetate andfiltered through celite, eluting with additional 10 mL of ethyl acetate.The filtrate was concentrated and the resulting residue waspurified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 25 - 70℃; for 20h; | To the solution of 56 (1.02 g, 5.34 mmol, 1.0 eq.) in DMF (17 mL) was added DBU (0.8 mL, 5.34 mmol, 1.0 eq.) and 57 (1 g, 5.34 mmol, l.Oeq.) at 25C. The reaction mixture was heated at 70 C for 20 h, then cooled to room temperature and quenched and with ice water. The aqueous layer was extracted with ethyl acetate (3 x 30 mL) and the combined organic layers were washed with a brine solution (2 x 30 mL), dried over anhydrous Na2S04, filtered and the solvent was removed in vacuo. The residue was purified by basic silica gel column chromatography (60-120 basic silica gel) using hexane/ethyl acetate as eluent (93:7) to afford 58 (l.27g, 33%) as a white solid. MS (ESI pos. ion) m/z: 359.2. |
Tags: 341-92-4 synthesis path| 341-92-4 SDS| 341-92-4 COA| 341-92-4 purity| 341-92-4 application| 341-92-4 NMR| 341-92-4 COA| 341-92-4 structure
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