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CAS No. : | 31191-08-9 | MDL No. : | MFCD10697538 |
Formula : | C6H5NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HSODMUBHOXGNNQ-UHFFFAOYSA-N |
M.W : | 123.11 | Pubchem ID : | 278389 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 31.65 |
TPSA : | 50.19 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.85 cm/s |
Log Po/w (iLOGP) : | 0.36 |
Log Po/w (XLOGP3) : | 0.29 |
Log Po/w (WLOGP) : | 0.6 |
Log Po/w (MLOGP) : | -0.84 |
Log Po/w (SILICOS-IT) : | 1.04 |
Consensus Log Po/w : | 0.29 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.21 |
Solubility : | 7.53 mg/ml ; 0.0612 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.91 |
Solubility : | 15.3 mg/ml ; 0.124 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.35 |
Solubility : | 5.46 mg/ml ; 0.0444 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.18 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
78% | With sodium hydroxide; | N-(5-Hydroxy-2-pyridinemethylene) hydroxylamine. To 200 mL of 2.5percent (w/w) sodium hydroxide solution was dissolved 5.5 g of 5-hydroxy-2-formylpyridine (45 mmol). Subsequently 12.5 g of hydroxylamine HCl (180 mmol) was added to the solution in one portion. The solution turned cloudy after being stirred for 10 minutes. After stirring at room temperature for 3 h, the precipitate was filtered under vacuum and dried in the air for several days to yield 4.8 g of N-(5-hydroxy-2-pyridinemethylene) hydroxylamine (78percent). The solid is of white and decomposes at 195° C. 1 H NMR (d6 -DMSO) delta: 11.27 (br. s, 1H); 10.83 (br. s, 1H); 8.18 (d, J=2 Hz, 1H); 8.05 (s, 1H, CH=N); 7.72 (d, J=9 Hz, 1H); 7.25 (d of d, J=2 Hz, 9 Hz, 1H). |
78% | With sodium hydroxide; | N-(5Hydroxy-2-pyridinemethylene) hydroxylamine. To 200 mL of 2.5percent (w/w) sodium hydroxide solution was dissolved 5.5 g of 5-hydroxy-2-formylpyridine (45 mmol). Subsequently 12.5 g of hydroxylamine HCl (180 mmol) was added to the solution in one portion. The solution turned cloudy after being stirred for 10 minutes. After stirring at room temperature for 3 h, the precipitate was filtered under vacuum and dried in the air for several days to yield 4.8 g of N-(5-hydroxy-2-pyridinemethylene) hydroxylamine (78percent). The solid is off white and decomposes at 195° C. 1 H NMR (d6 -DMSO) d: 11.27 (br. s, 1H); 10.83 (br. s, 1H); 8.18 (d, J=2 Hz, 1H); 8.05 (s, 1H, CH=N); 7.72 (d, J=9 Hz, 1H); 7.25 (d of d, J=2 Hz, 9 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With NaH; In water; N,N-dimethyl-formamide; | EXAMPLE 18 Preparation of 2-[(benzyloxycarbonyl)amino]-4-(5-hydroxy-2-pyridyl)-3-R,S-methylbutanoic acid. STR94 A. Methoxyethoxymethyl chloride (MEM) (19 g, 153 mmol) was added to a solution of <strong>[31191-08-9]5-hydroxy-2-pyridinecarboxaldehyde</strong> (18.4 g, 149 mmol)in 300 ml DMF. NaH (6.3 g of 60percent oil dispersion, 158 mmol) were added in portions while cooling the mixture to maintain 20°-30° C. The mixture was stirred an additional 1 hour at 25° C. 5 ml water were added, most of the solvent was evaporated, and water was added to the residue. The mixture was extracted with EtOAc. The extracts were dried over Na2 SO4, filtered, and evaporated to a residue. The residue was chromatographed on silica gel eluding with EtOAc-hexanes (35:65) to obtain 5-[(2-methoxyethoxy)methoxy]-2-pyridinecarboxaldehyde: C10 H13 NO4 (211.22); 1 H-NMR (CDCl3) delta 10.01 (s,1), 8.52 (d,1), 7.93 (d,1), 7.49 (m,1), 5.39 (s,2), 3.80 (m,2), 3.53 (m,2), 3.32 (s,3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.6 g (35%) | With ammonium chloride; In tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide; | EXAMPLE 6 2-[2-(1-Hydroxyhexyl)-5-pyridyloxy]quinoline To a suspension of sodium hydride (3.6 g, 0.15 mol) in dry DMF (150 ml) containing 2-chloroquinoline (24.5 g, 0.15 mol) was added dropwise a solution of <strong>[31191-08-9]5-hydroxypyridine-2-carboxaldehyde</strong> (18.5 g, 0.15 mol) in dry DMF (75 ml). The solution was stirred vigorously with a mechanical stirrer. After the addition was complete (90 min.), the reaction was heated to about 90° C. for 12 hours. Most of the DMF was removed, and the residue was carefully poured into cold water. The aqueous solution was extracted with ethyl acetate (4*30 ml), and the organic extract was washed with water, brine, and then dried over MgSO4. All volatiles were removed to leave the crude aldehyde intermediate (26 g) which was pure enough to be used in the next step. To a cold (-30° C.) solution of 5-(2-quinolinyloxy)-2-pyridine carboxaldehyde (8 g, 0.032 mol) in dry THF (125 ml) was added a solution of pentylmagnesium bromide (prepared from 4.83 g (0.032 mol) of 1-bromopentane and 0.78 g (0.032 mol) of Mg turnings in THF (60 ml). After the addition of the Grignard reagent was complete (-45° C.), the solution was stirred at this temperature for 90 minutes, and allowed to slowly warm up to room temperature in about 2 hours. The reaction was quenched by adding a saturated solution of ammonium chloride. The clear organic layer was decanted, and most of the volatiles were removed. The residue was taken up in ethyl acetate, and then washed with water, brine, and dried over MgSO4. After removal of the ethyl acetate the crude residue (7.7 g) was purified by HPLC (silica gel; 25percent ethyl acetate in hexane) to give 3.6 g (35percent) of pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With manganese(IV) oxide; In isopropyl alcohol; at 85℃; for 2h; | An activated MnO2 (2.5 times more in weight) was added to the <strong>[40222-77-3]6-(hydroxymethyl)pyridin-3-ol</strong> and the reactants were suspended in i-PrOH The reaction mixture was refluxed for 2 h (the boiling should not significantly exceed this time), after which it was cooled down and filtered. The resulting turbid dark solution was centrifuged and carefully decanted. The pure product could be obtained by recrystallization from boiling water as a brown crystalline solid. Yield 2.9 g (60 %). 1H NMR (400MHz, DMSO-d6 ): delta 11.10 (s, 1 H); 9.83 (s, 1 H); 8.32 (d, J = 2.2, 1 H); 7.85 (d, J = 9.5, 1 H); 7.33 (dd, J = 2.1, J = 8.6, 1 H); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 1h; | Anhydrous potassium carbonate (1 eq) and bromoethane (1 eq) were added to a solution of 5-hydroxy-pyridine-2-carbaldehyde (leq) in DMF (3.4ml / mmol). The reaction mixture was stirred at 1000C for Ih then diluted with water. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, dried on anhydrous Na2SO4 filtered and concentrated in vacuum to give the titled compound in 90percent yield. 1H-NMR (CDCl3): delta (ppm) 1.48 (t, 3H); 4.16 (q, 2H); 7.27 (dd, IH), 7.94 (d, IH); 8.41 (d, IH); 9.97 (s, IH); MS (ESI+): m/z = 152 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 1h; | Anhydrous potassium carbonate (1 eq) and 2-bromopropane (1 eq) were added to a solution of 5-hydroxy-pyridine-2-carbaldehyde (leq) in DMF (3.4ml/mmol). The reaction mixture was stirred at 100°C for Ih then diluted with water. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, dried on anhydrous Na2SO4 filtered and concentrated in vacuum to give the titled compound in 82percent yield. 1H-NMR (DMSO-t/6): delta (ppm) 1.40 (d, 6H); 4.70 (quint, IH); 7.25 (dd, IH); 7.94 (d, IH); 8.38 (d, IH); 9.97 (brs, IH); MS (ESI+): m/z = 166 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; at 120℃; for 4h; | General procedure: To a solution of 3-substituted 2-thioxo-1,3-thiazolidin-4-one 4 (1.0 equiv) and 3-bromo-4-hydroxybenzaldehyde (1.0 equiv) in acetic acid (4 mL/mmol) was added ammonium acetate (2.0 equiv) or beta-alanine (4.0 equiv). Then the mixture was stirred at 120 °C for 4 h. After cooling, the precipitate was collected by filtration and washed with water. The solid was triturated with ethanol to afford the title product (1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 65℃; for 24 - 48h;Reflux; | General procedure: Anhydrous iron (II) chloride(2 equiv.) was added to a stirred solution of either the desired chiral amine (3 equiv.) and 5-(2,2?-bipyridin-5-ylmethoxy)picolinaldehyde (3 equiv.) or the desired substituted aldehyde (3 equiv.) and (R)-2-(2,2?-bipyridin-5-ylmethoxy)-1-phenylethanamine (3 equiv.) in methanol (20 ml) at ambient temperature to give a purple solution that was then heated to reflux (65 C) for 24-48 h. The mixture was allowed to cool to ambient temperature, filtered through a celite plug, and the solvents were removed in vacuo to give a dark purple solid (>95% yield). Water of crystallization in these compounds was confirmed by NMR and infrared spectroscopy. The hydration number was then determined by thermogravimetric analysis and the relevant mass loss was correlated with microanalytical data. NMR, infrared and mass spectrometric data were consistent with the proposed formulations. CD spectra of enantiomers in water were equal and opposite. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 65℃; for 24 - 48h;Reflux; | General procedure: Anhydrous iron (II) chloride(2 equiv.) was added to a stirred solution of either the desired chiral amine (3 equiv.) and 5-(2,2?-bipyridin-5-ylmethoxy)picolinaldehyde (3 equiv.) or the desired substituted aldehyde (3 equiv.) and (R)-2-(2,2?-bipyridin-5-ylmethoxy)-1-phenylethanamine (3 equiv.) in methanol (20 ml) at ambient temperature to give a purple solution that was then heated to reflux (65 °C) for 24?48 h. The mixture was allowed to cool to ambient temperature, filtered through a celite plug, and the solvents were removed in vacuo to give a dark purple solid (>95percent yield). Water of crystallization in these compounds was confirmed by NMR and infrared spectroscopy. The hydration number was then determined by thermogravimetric analysis and the relevant mass loss was correlated with microanalytical data. NMR, infrared and mass spectrometric data were consistent with the proposed formulations. CD spectra of enantiomers in water were equal and opposite. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 65℃; for 24 - 48h;Reflux; | General procedure: Anhydrous iron (II) chloride(2 equiv.) was added to a stirred solution of either the desired chiral amine (3 equiv.) and 5-(2,2?-bipyridin-5-ylmethoxy)picolinaldehyde (3 equiv.) or the desired substituted aldehyde (3 equiv.) and (R)-2-(2,2?-bipyridin-5-ylmethoxy)-1-phenylethanamine (3 equiv.) in methanol (20 ml) at ambient temperature to give a purple solution that was then heated to reflux (65 °C) for 24?48 h. The mixture was allowed to cool to ambient temperature, filtered through a celite plug, and the solvents were removed in vacuo to give a dark purple solid (>95percent yield). Water of crystallization in these compounds was confirmed by NMR and infrared spectroscopy. The hydration number was then determined by thermogravimetric analysis and the relevant mass loss was correlated with microanalytical data. NMR, infrared and mass spectrometric data were consistent with the proposed formulations. CD spectra of enantiomers in water were equal and opposite. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 65℃; | General procedure: Anhydrous iron(II) chloride (2 equiv.) was added to a stirred solution of either the desired chiral amine (3 equiv.)and 5-(2,2?-bipyridin-5-ylmethoxy)picolinaldehyde (3 equiv.) or the desired substituted aldehyde (3 equiv.) and (R)-2-(2,2?-bipyridin-5-ylmethoxy)-1-phenylethanamine (3 equiv.) in methanol (20 ml) at ambient temperature to give a purple solution that was then heated to reflux (65 °C) for 24?48 h. The mixture was allowed to cool to ambient temperature, filtered through a celite plug, and the solvents were removed in vacuo to give a dark purple solid (>95percent yield). Water of crystallization in these compounds was confirmed by NMR and infrared spectroscopy. The hydration number was then determined by thermogravimetric analysis and the relevant mass loss was correlated with microanalytical data. NMR, infrared and mass spectrometric data were consistent with the proposed formulations. CD spectra of enantiomers in water were equal and opposite. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 65℃; | General procedure: Anhydrous iron(II) chloride (2 equiv.) was added to a stirred solution of either the desired chiral amine (3 equiv.)and 5-(2,2?-bipyridin-5-ylmethoxy)picolinaldehyde (3 equiv.) or the desired substituted aldehyde (3 equiv.) and (R)-2-(2,2?-bipyridin-5-ylmethoxy)-1-phenylethanamine (3 equiv.) in methanol (20 ml) at ambient temperature to give a purple solution that was then heated to reflux (65 C) for 24-48 h. The mixture was allowed to cool to ambient temperature, filtered through a celite plug, and the solvents were removed in vacuo to give a dark purple solid (>95% yield). Water of crystallization in these compounds was confirmed by NMR and infrared spectroscopy. The hydration number was then determined by thermogravimetric analysis and the relevant mass loss was correlated with microanalytical data. NMR, infrared and mass spectrometric data were consistent with the proposed formulations. CD spectra of enantiomers in water were equal and opposite. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 4h;Schlenk technique; Inert atmosphere; | A mixture of 5-(hydroxy)picolinaldehyde (1; 51 mg, 0.4 mmol), 1-bromo-4-thiocyanatobutane (2; 119 mg, 0.6 mmol) and anhydrous potassium carbonate (72 mg, 0.5 mmol) was stirred vigorously in N,N-dimethyl formamide (6 mL) at 100°C for 4 h. After the mixture had cooled to room temperature, water (18 mL) was added, the suspension extracted with diethyl ether (310 mL), and the combined extracts dried over Na2SO4. The solvent was evaporated on a rotary evaporator and the residue purified by column chromatography on silica gel using hexane-ethylacetate (1:1) as eluent (Rf =0.42) to give thiocyanate 3 as a yellow oil (43 mg, 29percent). ? 1H NMR (400 MHz, [D]chloroform, 25°C): d =9.97 (s, 1 H; CHO), 8.41 (dd,J =2.4, 0.5 Hz, 1 H; HAryl), 7.95 (dd, J =8.2, 0.6 Hz, 1H; HAryl), 7.28 (ddd, J =8.2, 2.4, 0.6 Hz, 1 H; HAryl), 4.15 (t, J =5.8 Hz, 2 H; O?CH2-), 3.05 (t, J =6.8 Hz, 2H; -CH2?SCN), 2.08 ? 2.01 (m, 4H; -CH2?CH2-) ppm. ?13C NMR (100.6 MHz, [D]chloroform, 25°C): d =191.9 (CHO), 158.0 (CAryl), 146.4 (CAryl), 138.6 (CAryl), 123.3 (CAryl), 120.4 (CAryl), 111.9 (SCN), 67.7 (O?CH2-), 33.5(-CH2?SCN), 27.2 (-CH2?CH2-), 26.6 (-CH2?CH2-) ppm.? IR (MeOH): n =2154 (s), 1708(s), 1573 (s) cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With caesium carbonate; In acetonitrile; | To a stirred solution of 2-(2-(bromomethyl)-4-fluorophenyl)-5-methylthiophene (0.200g, 1.625 mM) and 5-hydroxypicolinaldehyde (0.435g, 1.625) in dry acetonitrile, cesium carbonate (0.794g, 2.43 mM) was added and stirred overnight. The mixture was filtered and residue was washed with acetonitrile. The filtrate was concentrated to give 5-((2- bromo-5- fluorobenzyl)oxy)picolinaldehyde. Yield: 0.38 g, 76percent; JH NMR (300 MHz, DMSO-d6) delta: delta 9.90 (s, 1H), 8.62-8.61 (d, / = 8.7 Hz, 1H), 7.99-7.96 (d, / = 9.3Hz,lH),7.77- 7.70 (m, 2H), 7.57-7.53 (dd, / = 3, 9.3 Hz, 1H), 7.28-7.22 (m,lH),5.31 (s,2H); MS (E/Z): 311.9 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 0 - 20℃; for 17h; | A stirred solution of (R,E)-3-(4-chloro-2-((5-methyl-2H-tetrazol-2-yl)methyl)phenyl)- 1-(2-methylpiperazin-1-yl)prop-2-en-1-one (intermediate A) ( 3.0 g, 8.3 mmol) in DCE (60 mL) was treated with <strong>[31191-08-9]5-hydroxypyridine-2-carboxaldehyde</strong> (2.0 g, 16.6 mmol), sodium triacetoxyborohydride (3.5 g, 16.62 mmol) and acetic acid (0.95 mL) at 0C. The resulting mixture was stirred at RT for 17 h. The solvent was evaporated, water was added to the residue, and the aqueous phase was extracted with EtOAc. The organic layer was washed with sat. aq. NaHCO3, brine, dried over Na2504, filtered and concentrated under vacuum. The residue was purified by flash chromatography on silica gel.HLPC Rt: 5.7 mm (analytical HPLC) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium acetate; In water; at 80℃; for 2h; | Heat the aqueous solution (5 ml) of ethoxyamino hydrochloride (244 mg, 2.5 mmol), 5-hydroxy-pyridine-2-aldehyde (308 mg, 2.5 mmol), sodium acetate (410 mg, 5.0 mmol) to 80° C. to agitate 2 hours. After TLC indicates the raw materials disappear, extract the reaction mixture with ethyl acetate (10 ml×3). Mix the organic phases and dry with anhydrous Na2SO4 before filter and concentrate to obtain the title compound (white solid, 410 mg, yield of 99percent) that is directly used without necessity to purify further. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19.5 g | In tetrahydrofuran; at 50℃;Inert atmosphere; | B) Ethyl 3-(5-hydroxypyridin-2-yl)acrylate A mixture of 5-hydroxypicolinaldehyde (20.8 g), [(ethoxycarbonyl)methylene]triphenylphosphorane (76.5 g), and tetrahydrofuran (1000 mL) was stirred under a nitrogen atmosphere at 50° C. overnight. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to obtain the title compound (19.5 g). MS: [M+H]+ 193.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 110℃; for 2h; | To a solution of <strong>[31191-08-9]5-hydroxypyridine-2-carbaldehyde</strong> (77 mg, 0.625 mmol) in DMF (4.0 mL) was added K2CO3 (86.4 mg, 0.625 mmol) at 0° C., followed by 4-(5-bromopentylsulfanyl)-7-(trifluoromethyl)quinoline (197 mg, 0.521 mmol) and the reaction mixture was stirred at 110° C. for 2 h. The mixture was poured into H2O (6.0 mL) and the aqueous layer was extracted with DCM (3*25 mL). The combined organic layers were washed with brine (2*25 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. The material was purified by column chromatography on silica gel (12 g) using a gradient of 0-10percent MeOH in DCM as eluent to afford title compound (175 mg, 80percent) as a solid. 1H NMR (500 MHz, CDCl3) delta 9.99 (d, J=0.8 Hz, 1H), 8.80 (d, J=4.8 Hz, 1H), 8.43 (d, J=2.3 Hz, 1H), 8.37 (s, 1H), 8.25 (d, J=8.8 Hz, 1H), 7.96 (dd, J=8.6, 0.5 Hz, 1H), 7.72 (dd, J=8.7, 1.9 Hz, 1H), 7.28 (dd, J=8.9, 3.7 Hz, 2H), 4.14 (t, J=6.2 Hz, 2H), 3.18 (t, J=7.2 Hz, 2H), 1.97-1.89 (m, 4H), 1.77 (dd, J=15.4, 8.1 Hz, 2H). MS (ESI) [M+H]+ 421.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | General procedure: A mixture of amine (1 mmol) and aldehyde (1 mmol) in 3 mL ofabsolute ethanol was refluxed for 2 h followed by addition of cyclicketone (2.5 mmol) to the reaction mixture. A catalytic amount ofconc. hydrochloric acid was added, and the reaction was continuedto reflux for 6?12 h. Reaction mixture dissolved in ethyl acetate(50 mL), washed with sodium bicarbonate solution and water(10 mL 2). The organic layer was dried (Na2SO4), concentratedunder reduced pressure, and purified by silica gel chromatography [dichloromethane:methanol (99:01 to 80:20) or hexane:ethylacetate(20:80 to 05:95)] to give the desired cyclized compound.(Note: Sometime product may get precipitated out, which was filtered,washed with absolute ethanol and further purified by columnchromatography). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Tetrahydrofuran (100 mL) was cooled to 0 ° C under nitrogen, and sodium hydride (1.95 g, 48.8 mmol, 60 mass percent) was added portionwise.Subsequently, triethyl phosphonoacetate (10.9 g, 48.6 mmol) was added.After the obtained reaction mixture was stirred at this temperature for 20 minutes, a solution of <strong>[31191-08-9]5-hydroxypyridine-2-carbaldehyde</strong> 30a (2.00 g, 16.2 mmol) in tetrahydrofuran (10 mL) was added dropwise.After adding water (100 mL), the mixture was quenched with hydrochloric acid (1 mol/L), and the organic solvent was evaporated under reduced pressure. The residue was extracted with ethyl acetate (100 mL×4).The combined organic layers were dried over anhydrous sodium[ethyl acetate / petroleum ether (v / v) = 1 / 1] purified to give the title compound30b (2.66 g, 85percent yield) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 90% | In ethanol; at 80℃; for 12h; | Synthesized according the general procedure for L1. Obtained as a white solid in >90% yield. 1H-NMR (400MHz, DMSO-d6): delta 10.30 (s, 2 H); 8.45-8.48 (m, 2 H); 8.21 (d, J = 2.7, 2 H); 7.95 (d, J = 8.5, 2 H); 7.90 (s, 2 H); 7.70 (s, 1 H); 7.54 (t, J = 3.4, 3 H); 7.35 (dd, J= 2.7, J = 8.5, 2 H); 3.77 (s, 6 H); 13C-NMR (400MHz, DMSO-d6): 162.62; 164.42; 153.88; 145.78; 137.65; 137.61; 137.24; 130.49; 128.36; 127.75; 122.98; 119.96; 85.41; 29.36; ESI-MS: 455.1941, calc. 455.1938 (M+H+) M.p.: 341-343 C (decomposition) UV-Vis (DMSO (1.61x10-5 M): lambdamax nm (epsilon, M-1cm-1) 249 nm (24544 M-1 cm-1); 302 (54773 M-1 cm-1); 344.5 (28540 M-1 cm-1); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 24h; | A <strong>[31191-08-9]5-hydroxy-2-pyridinecarboxaldehyde</strong> (1 eq. 6.2 mmol), methyl bromoacetate (1 eq. per -CH2OH, 6.2 mmol) and K2CO3 (4 eq. per -CH2OH, 24.8 mmol) were dissolved in dry DMF (20 ml). The resulting mixture was heated at 70 C for 24 h. During this time the reaction mixture changed colour from orange to dark brown. The solvent was then evaporated and crude product was extracted into CH2Cl2. The pure oily product was obtained via flash chromatography on silica (gradient Heptane : EtOAc) in 57 % yield. 1H-NMR (400MHz, CDCl3): 10.01 (s, 1 H); 8.47 (d, J = 2.9, 1 H); 7.97 (d, J = 8.8, 1 H); 7.29 (dd, J = 2.8, J = 8.8, 2 H); 4.78 (s, 2 H); 3.84 (s, 3 H); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 24h; | <strong>[31191-08-9]5-hydroxy-2-pyridinecarboxaldehyde</strong> (1 eq.), N-(2-Bromoethyl)phthalimide (1 eq, 6.2 mmol) and K2CO3 (4 eq.) were dissolved in dry DMF (20 ml) and resulting mixture was heated at 70 C for 24 h. After evaporation of DMF, the residue was dissolved in CH2Cl2 and washed with water. The organic phase was collected and water phase was re-extracted two times with CH2Cl2. The organic phases was evaporated and the crude product purified by flash chromatography on silica (gradient of EtOAc : Petrol ether 1:4 to 2:1). The product was obtained as white solid in 63% yield. 1H-NMR (400MHz, CDCl3): 9.97 (s, 1 H); 8.40 (d, J = 2.7, 1 H); 7.93 (d, J = 8.8, 1 H); 7.89 (q, J = 2.8, 2 H); 7.75 (q, J = 2.8, 2 H); 7.30 (dd, J = 8.6, J = 2.6 , 1 H); 4.38 (t, J = 5.6, 2 H); 4.17 (t, J = 5.6, 2 H); 13C NMR (100MHz, CDCl3): 191.92, 168.04, 157.69, 146.70, 138.73, 134.28, 131.89, 123.54, 123.25, 120.80, 65.44, 36.88, ESI-MS: 297.0825, calc 297.0870 (M+H+) M.p.: 139-140C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With acetic acid; In toluene; at 80℃; for 2h;Inert atmosphere; | Intermediate 6c: 6-((1S,3R)-2-(2,2-Difluoroethyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)pyridin-3-ol (R)-N-(2,2-Difluoroethyl)-1-(1H-indol-3-yl)propan-2-amine (4 g, 16.79 mmol) and 5-hydroxypicolinaldehyde (2.118 g, 17.21 mmol) were heated to 80 C. in toluene (80 mL) and AcOH (8.88 mL) for 2 hours under nitrogen. The mixture was evaporated, then the residue was dissolved in EtOAc (100 mL) and washed with sat. aq. NaHCO3 solution (50 mL), dried (MgSO4) and evaporated to afford crude product as a dark orange oil. The crude product was absorbed onto silica and purified by flash column chromatography, elution gradient 0 to 50% EtOAc in heptane to afford the title compound (4.30 g, 75%) as a cream solid; 1H NMR (400 MHz, DMSO-d6) 1.12 (3H, d), 2.57 (1H, q), 2.62-2.76 (2H, m), 3.13 (1H, m), 3.28 (1H, d), 4.94 (1H, s), 5.99 (1H, m), 6.95 (1H, m), 7-7.09 (1H, m), 7.15 (1H, dd), 7.24 (2H, dd), 7.41 (1H, d), 8.06 (1H, dd), 9.81 (1H, s), 10.53 (1H, s); m/z: ES+ [M+H]+ 344.2. |
Tags: 31191-08-9 synthesis path| 31191-08-9 SDS| 31191-08-9 COA| 31191-08-9 purity| 31191-08-9 application| 31191-08-9 NMR| 31191-08-9 COA| 31191-08-9 structure
[ 67310-56-9 ]
1-(5-Hydroxypyridin-2-yl)ethanone
Similarity: 0.88
[ 30766-12-2 ]
Methyl 5-hydroxypyridine-2-carboxylate
Similarity: 0.78
[ 127978-70-5 ]
(5-Methoxypyridine-2-yl)methanol
Similarity: 0.73
[ 67310-56-9 ]
1-(5-Hydroxypyridin-2-yl)ethanone
Similarity: 0.88
[ 29082-92-6 ]
5-Methoxy-2-pyridinecarboxylic acid
Similarity: 0.78
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