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CAS No. : | 55758-32-2 | MDL No. : | MFCD01075040 |
Formula : | C5H4FNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HTRLNWYWOKWCLV-UHFFFAOYSA-N |
M.W : | 113.09 | Pubchem ID : | 2763108 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 26.22 |
TPSA : | 33.12 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) : | -6.33 cm/s |
Log Po/w (iLOGP) : | 0.98 |
Log Po/w (XLOGP3) : | 0.93 |
Log Po/w (WLOGP) : | 1.35 |
Log Po/w (MLOGP) : | 0.21 |
Log Po/w (SILICOS-IT) : | 1.39 |
Consensus Log Po/w : | 0.97 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.68 |
Solubility : | 2.35 mg/ml ; 0.0208 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.21 |
Solubility : | 6.94 mg/ml ; 0.0614 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.67 |
Solubility : | 2.42 mg/ml ; 0.0214 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.52 |
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 |
---|---|---|
79% | With hydrogenchloride In sodium hydroxide | 8e. 2-Fluoro-5-hydroxypyridine 5-acetoxy-2-fluoropyridine (2.26 g, 14.6 mmol, from step 8d above) was dissolved in 20percent aqueous NaOH (15 mL). After stirring at ambient temperature for 1 hour the solution was neutralized by addition of concentrated HCl. The aqueous mixture was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), and the solvent was evaporated. Purification by chromatography (silica gel; CHCl3 /MeOH, 98:2) afforded 1.31 g (79percent) of the title compound: MS m/z: 114 (M+H)+, 131 (M+NH4)+; 1 H NMR (CDCl3, 300 MHz) δ 6.84 (dd, J=1.85, 5.14 Hz, 1 H), 7.43 (m, 1 H), 7.81 (t, J=2.84 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A three neck 3-L flask equipped with an overhead stirred was charged with 6- fluoropyridin-3-ylboronic acid (105 g, 745 mmol) and 1L of THF. The mixture was cooled to 0 C and NaOH 6N (373 mL, 2235 mmol) was added. To the resulting mixture was added hydrogen peroxide 30% (126 mL, 4098 mmol), dropwise via an addition funnel over the course of 30 minutes. After stirring at 0 C for 2 hours the mixture was removed from the ice bath and maintained at RT for 30 minutes. The reaction was acidified to pH 7 with 6 N HC1 (ca. 300 mL) and diluted with 500 mL of ether. The aqueous layer was extracted with ether (2 x 1 L) and the combined organic layers were washed with water (1.5 L) then brine before being dried over sodium sulfate. Filtration and concentration provided a white solid that was dried on high vac overnight to provide 6-fluoropyridin-3-ol. | ||
Example 35. Polyphosphoric acid, 140 CSynthesis of 7-Bromo-3-methoxy-5H-chromeno[2,3-b]pyridin-5-one; Step 1 : A three neck 3-L RBF equipped with an overhead stirred was charged with 6- fluoropyridin-3-ylboronic acid (105 g, 745 mmol) and 1L of THF. The mixture was cooled to 0 C and NaOH 6N (373 mL, 2235 mmol) was added. To the resulting mixture was added hydrogen peroxide 30% (126 mL, 4098 mmol), dropwise via an addition funnel over the course of 30 minutes. After stirring at 0 C for 2 hours the mixture was removed from the ice bath and maintained at RT for 30 minutes. The reaction was acidified to pH 7 with 6 N HC1 (ca. 300 mL) and diluted with 500 mL of ether. The aqueous layer was extracted with ether (2 x 1 L) and the combined organic layers were washed with water (1.5 L) then brine before being dried over sodium sulfate. Filtration and concentration provided a white solid that was dried on high vac overnight to provide 6-fluoropyridin-3 -ol. | ||
Example 35. Polyphosphoric acid, 140 CSynthesis of 7-Bromo-3-methoxy-5H-chromeno[2,3-b]pyridin-5-oneStep 1 : A three neck 3-L RBF equipped with an overhead stirred was charged with 6- fluoropyridin-3-ylboronic acid (105 g, 745 mmol) and 1L of THF. The mixture was cooled to 0 C and NaOH 6N (373 mL, 2235 mmol) was added. To the resulting mixture was added hydrogen peroxide 30% (126 mL, 4098 mmol), dropwise via an addition funnel over the course of 30 minutes. After stirring at 0 C for 2 hours the mixture was removed from the ice bath and maintained at RT for 30 minutes. The reaction was acidified to pH 7 with 6 N HC1 (ca. 300 mL) and diluted with 500 mL of ether. The aqueous layer was extracted with ether (2 x 1 L) and the combined organic layers were washed with water (1.5 L) then brine before being dried over sodium sulfate. Filtration and concentration provided a white solid that was dried on high vac overnight to provide 6-fluoropyridin-3 -ol. |
A three neck 3-L RBF equipped with an overhead stirred was charged with 6- fluoropyridin-3-ylboronic acid (105 g, 745 mmol) and 1L of THF. The mixture was cooled to 0 C and NaOH 6N (373 mL, 2235 mmol) was added. To the resulting mixture was added hydrogen peroxide 30% (126 mL, 4098 mmol), dropwise via an addition funnel over the course of 30 minutes. After stirring at 0 C for 2 hours the mixture was removed from the ice bath and maintained at RT for 30 minutes. The reaction was acidified to pH 7 with 6 N HC1 (ca. 300 mL) and diluted with 500 mL of ether. The aqueous layer was extracted with ether (2 x 1 L) and the combined organic layers were washed with water (1.5 L) then brine before being dried over sodium sulfate. Filtration and concentration provided a white solid that was dried on high vac overnight to provide6-fluoropyridin-3 -ol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With caesium carbonate; In acetone; at 55℃; for 16h; | EXAMPLE 10A.[00166] To a solution of <strong>[55758-32-2]6-fluoropyridin-3-ol</strong> (43.5 mg, 0.385 mmol) and 5- bromothiazol-2-amine hydrobromide (100 mg, 0.385 mmol) in acetone (5 mL) was added CS2CO3 (276 mg, 0.846 mmol). The reaction was stirred at 55C for 16 h, then was cooled to RT. The mixture was filtered and washed with acetone. The combined filtrates were concentrated in vacuo, then were partitioned between EtOAc and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by preparative HPLC (Phenomenex Luna AXIA 5u C18 30 x 100 mm column; detection at 220 nm; flow rate = 40 mL/min; continuous gradient from 10% B to 100% B over 10 min + 2 min hold time at 100% B, where A = 90: 10:0.1 H2O:MeOH:TFA and B = 90: 10:0.1 MeOH:H2O:TFA) to give the Part A compound (45mg, 55% yield) as a white solid. |
34% | With caesium carbonate; In acetone; for 12h;Heating / reflux; | To a solution of 5-bromothiazol-2-amine hydrobromide (100 mg, 0.39 mmol) in acetone (2 mL) was added <strong>[55758-32-2]2-fluoro-5-hydroxy pyridine</strong> (44 mg, 0.39 mmol) and cesium carbonate (251 mg, 0.77 mmol). The reaction mixture was stirred at reflux for 12 h, then was cooled to RT. The mixture was filtered and solids were washed with acetone. The filtrates was concentrated in vacuo. The residue was partitioned between EtOAc and H2O. The organic phase was washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by preparative HPLC (Phenomenex Luna 5u C18 21.2×100 mm column; detection at 220 nm; flow rate=20 mL/min; continuous gradient from 10% B to 100% B over 8 min+7 min hold time at 100% B, where A=90:10:0.1 H2O:MeOH:TFA and B=90:10:0.1 MeOH:H2O:TFA) to provide Part A compound (28 mg, 34%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With dmap; In 1,2-dichloro-benzene; at 140℃; for 3.5h; | Compound 205: 4-(6-Fluoro-pyridin-3-yloxy)-6,7-dimethoxy-quinoline; 6-Fluoro-3-hydroxypyridine (10 mg), 4-chloro-6,7-dimethoxyquinoline (59 mg), and 4-dimethylaminopyridine (32 mg) were suspended in o-dichlorobenzene (2 ml), and the suspension was stirred at 140C for 3.5 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (20 mg, yield 76%). 1H-NMR (CDCl3, 400 MHz): delta 3.98 (s, 6H), 6.35 (d, J = 5.2 Hz, 1H), 6.99 (dd, J = 8.8 Hz, 3.6 Hz, 1H), 7.36 (s, 1H), 7.44 (s, 1H), 7.56 (m, 1H), 8.09 (s, 1H), 8.46 (d, J = 5.2 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 301 (M+1)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In N,N-dimethyl-formamide; | Example 232B 5-(tert-Butyl-dimethyl-silanyloxy)-2-fluoro-pyridine A mixture of <strong>[55758-32-2]2-fluoro-5-hydroxypyridine</strong> (1.00 g, 8.84 mmol) and BDCS reagent (0.5M TBSCl, 1.0M imidazole in DMF) (35.4 mL, 17.7 mmol) was stirred at rt for 1 h. The reaction was poured into satd. aqueous NaHCO3 solution. The aqueous layer was extracted with ether. The combined extracts were washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by flash column chromatography on silica gel eluding with 10% ethyl acetate/hexanes to give the title compound (1.96 g, 98%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 1h; | Example 232B 5-(tert-Butyl-dimethyl-silanyloxy)-2-fluoro-pyridine A mixture of <strong>[55758-32-2]2-fluoro-5-hydroxypyridine</strong> (1.00 g, 8.84 mmol) and BDCS reagent (0.5M TBSCl, 1.0M imidazole in DMF) (35.4 mL, 17.7 mmol) was stirred at rt for 1 h. The reaction was poured into satd. aqueous NaHCO3 solution. The aqueous layer was extracted with ether. The combined extracts were washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by flash column chromatography on silica gel eluding with 10% ethyl acetate/hexanes to give the title compound (1.96 g, 98%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 40 2-Fluoro-5-(3-(S)-pyrrolidinylmethoxy)pyridine 4-methylbenzenesulfonate The title compound was prepared according to the procedures of Examples 39c and d, using <strong>[55758-32-2]2-fluoro-5-hydroxypyridine</strong> (NCK Chemicals, Denmark) in place of the 2-chloro-5-hydroxypyridine therein. mp 109-110 C.; MS (DCI-NH3) m/z 197 (M +H)+; 1H NMR (300 MHz, CDCl3) delta1.85-2.0 (m, 1 H), 2.15-2.30 (m, 1 H), 2.36 (s, 3H), 2.75-2.92 (m, 1 H), 3.30-3.45 (m, 2 H), 3.42-3.62 (m, 2H), 3.95 (d, J=6 Hz, 2H), 6.75 (dd, J=9 Hz,Hz, 1H), 7.16 (d, J=7.5 Hz, 2H), 7.25 (dd, J=9 Hz 6 Hz, 1 H), 7.65-7.75 (m, 3H), 9.25 (bs, 1H); Analysis calculated for C10H13FN2O.C7H8O3S.0.25 H2O: C, 54.75; H, 5.81; N, 7.51. Found: C, 54.85; H, 5.56; N, 7.59; [alpha]D23 -4.65 (c 0.2, MeOH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In sodium hydroxide; | 136e. 2-fluoro-5-hydroxypyridine 5-Acetoxy-2-fluoropyridine (70.5 g, 454 mmol) from step 136d above was suspended in 20% aqueous NaOH (200 mL) at 0 C. and stirred at ambient temperature overnight. The solution was neutralized (pH 6) by the addition of concentrated HCl. The aqueous mixture was extracted with EtOAc (5*200 mL), then the combined organic extracts were dried (MgSO4), and concentrated to afford 47.9 g (93%) of a solid. The crude product was recrystallized from EtOAc to afford the title compound as a white solid (30.5 g, 59%). The 2nd and 3rd crops were combined and recrystallized to afford an additional 9.3 g (18%) of the title compound: 1 H NMR (CDCl3, 300 MHz) delta 6.84 (dd, J=1.9, 5.1 Hz, 1H), 7.43 (m, 1H), 7.81 (t, J=2.8 Hz, 114); MS m/z: 114 (M+H)+, 131 (M+NH4)+. | |
1.31 g (79%) | With hydrogenchloride; In sodium hydroxide; | 8e. 2-Fluoro-5-hydroxypyridine 5-acetoxy-2-fluoropyridine (2.26 g, 14.6 mmol, from step 8d above) was dissolved in 20% aqueous NaOH (15 mL). After stirring at ambient temperature for 1 hour the solution was neutralized by addition of concentrated HCl. The aqueous mixture was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), and the solvent was evaporated. Purification by chromatography (silica gel; CHCl3 /MeOH, 98:2) afforded 1.31 g (79%) of the title compound: MS m/z: 114 (M+H)+, 131 (M+NH4)+; 1 H NMR (CDCl3, 300 MHz) delta 6.84 (dd, J=1.85, 5.14 Hz, 1 H), 7.43 (m, 1 H), 7.81 (t, J=2.84 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With iodine; In methanol; water; at 20℃; for 167h; | 2-Fluoro-5-hydroxypyridine (2.00 g) and iodine (44.9 g) were dissolved in a mixed solvent composed of methanol (40 ml) and water (20 ml), and the mixture was stirred at room temperature for 167 hr. Sodium sulfite was added to the reaction mixture until the solution became transparent. Methanol was then removed from the reaction mixture under the reduced pressure. Water was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-chloroform system to give 6-fluoro-2-iodo-pyridin-3-ol (761 mg, yield 18%). 6-Fluoro-2-iodo-pyridin-3-ol (135 mg), 4-chloro-6,7-dimethoxyquinoline (378 mg), and 4-dimethylaminopyridine (207 mg) were suspended in 1,2-dichlorobenzene (8 ml), and the suspension was stirred at 130C for 3.5 hr. The reaction mixture was cooled to room temperature, and water was added thereto. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-hexane system to give 4-(6-fluoro-2-iodo-pyridin-3-yloxy)-6,7-dimethoxy-quinoline (89 mg, yield 37%). |
136f. 6-fluoro-2-iodo-3-pyridinol The title compound was prepared from <strong>[55758-32-2]2-fluoro-5-hydroxypyridine</strong> (from step 136e above) according to the procedures of step 28d above: 1 H NMR (DMSO-d6, 300 MHz) delta 7.03 (dd, J=3.9, 8.7 Hz, 1H), 7.30 (dd, J=7.0, 8.6 Hz, 1H), 10.81 (br s, 1H); MS m/z: 240 (M+H)+, 257 (M+NH4)+. | ||
19.8 g | To a stirring solution of <strong>[55758-32-2]6-fluoro-3-hydroxypyridine</strong> (10 g, 88.496 mmol) in THF (300 mL) was added slowly Na2CO3 (19.697 g, 185.841 mmol) in water (300 mL) at 0 C and stirred for 20 mins. Iodine (22.46 1 g, 88.496 mmol) was added portion wise at 0 C and the reaction mass was allowed to stir at room temperature for overnight. Solvent was evaporated; aqueous part was neutralized with iN HC1, extracted with ethyl acetate. Organic layer was separated, dried over anhydrous Na2SO4 and evaporated under reduce pressure to give crude mass which was triturated with DCM/pentane to get 6-fluoro-3-hydroxy-2-iodopyridine (19.8 g) as a brown solid. ?H-NMR (400 MHz, DMSO): oe 10.79 (s, 1H), 7.3 1-7.27 (m, 1H), 7.03-7.00 (m, 1H); LCMS: 239.8 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 51; 4-[{2-[(6-Fluoro-3-pyridinyl)oxy]ethyl}(2,2,2-trifluoroethyl)amino]-2- (trifluoromethyl)benzonitrile; A. 6-Fluoro-3-pyridinol; To a solution of 5-bromo-2-fluoropyridine (0.26 mL, 2.5 mmol) in dry Et2O (10 mL) at -78C was added n-BuLi (1.06 mL of a 2.5 M solution in hexanes, 2.7 mmol), dropwise over 3 min. The mixture was stirred 15 min and B(O/-Pr)3 (0.64 mL, 2.8 mmol) was added dropwise. The mixture was gradually warmed to rt over 30 min, 1 M NaOH (2 mL) was added, followed by H2O2 (0.5 mL of a 30 wt% solution) and the mixture was stirred 30 min. Excess H2O2 was quenched by dropwise addition of a 10% solution of Na2S2O3, the mixture was poured into water and the layers were separated. The aqueous layer was adjusted to pH 3.5 by addition of 1M KHSO4 and extracted with EtOAc (x3). Combined organics portions were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.242 g of the title compound as a colorless solid: MS (APCI) m/z 114 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.4% | Preparation 17; 2-Fluoro-5-methoxymethoxy -pyridine; Add 6-fluoro-pyridin-3-ol (3.5 g, 30.95 mmol) to a suspension of sodium hydride (1.49 g, 37.14 mmol) in dimethylformamide (20 mL). Stir the mixture for 1 hour. Add chloromethyl methyl ether (2 g, 25.0 mmol). Stir the mixture at room temperature overnight. Dilute the mixture with ethyl acetate and water. Wash the organic layer with water and saturated aqueous sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to brown oil. Purify by column chromatography (10 % ethyl acetate in hexane) to afford the title compound (4.30 g, 88.4 %) as yellow oil. 1H NMR (400 MHz, CDCl3) delta 3.48 (s, 3H), 5.15 (s, 2H), 6.85 (dd, J= 3.6 Hz, J= 8.8 Hz, IH), 7.47 (m, 1 H), 7.96 (m, IH). | |
88% | 2-Fluoro-5-methoxymethoxy -pyridineAdd 6-fluoro-pyridin-3-ol (3.5 g, 30.95 mmol) to a suspension of sodium hydride (1.49 g, 37.1 mmol) in DMF (20 mL). Stir the mixture for 1 h. Add chloromethyl methyl ether (2 g, 25.0 mmol). Stir the mixture at RT overnight. Dilute the mixture with ethyl acetate and water. Wash the organic layer with water and aqueous saturated sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (10 % ethyl acetate in hexane) to afford the title compound (4.30 g, 88 %) as yellow oil. 1H NMR (400 MHz, CDCl3) delta 3.48 (s, 3H), 5.15 (s, 2H), 6.85 (dd, J= 3.6 Hz, J= 8.8 Hz, IH), 7.47 (m, 1 H), 7.96 (m, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of [2-FLUORO-5-HYDROXYPYRIDINE] (1.77 mmol) in DMF (4 ml) was added NaH [(60%] dispersion in mineral oil, 4.42 mmol) in small portions at room temperature and under an atmosphere of nitrogen. After stirring for 1 hour, tetra-n-butylammonium chloride (17.68 Mol) was added, followed by 2-chloro-5-nitrobenzyl bromide (5.31 mmol) (see above). After stirring for a further 17 hours, [MEOH] (2 ml) and then water (2 ml) were added. The DMF was removed in vacuo and the residue was partitioned between ethyl acetate (50 ml) and water (25 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2 x 40 ml). The combined organic extracts were then dried [(MGSO4),] filtered and concentrated. Purification by flash chromatography eluting with EtOAc/40-60 petroleum ether (1: 19) gave the desired compound as a pale yellow oil. bH [(400] MHz; [CDC13)] 5.23 (2H, s), 6.94 [(1H,] dd, [J 8.] 8 and 3.5), 7. [46-7.] 51 [(1H,] m), 7.61 [(1H,] d, [J 8.] 8), 7.95-7. 98 [(1H,] m), 8.19 (1H, dd, J 8. 6 and 2.6), 8. 49 (1H, d, [J 2.] 6). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.5% | To a 0 0C suspension Of Cs2COs (18.73 g, 57.48 mmol) in 150 mL DMF was added 6-fluoropyridin-3- ol (5.0 g, 44.21 mmol). The cloudy brown mixture was stirred for 15 minutes, then 1-bromo- 2-methoxyethane (6.232 mL, 66.32 mmol) was added. The reaction mixture was heated in a 110 0C sand bath and stirred for 17 hours, after which it was cooled to ambient temperature and the DMF was removed in vacuo. The resulting residue was combined with saturated NH4Cl and the mixture was extracted with DCM. The combined extracts were dried (Na2SO4), filtered, and concentrated. The crude material was purified on silica gel (5-50% ethyl acetate in hexanes gradient) to give the desired product (7.00 g, 92.50 % yield) as a clear, colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With caesium carbonate; In N,N-dimethyl acetamide; at 100℃; for 12h;Inert atmosphere; | Preparation of 5-[2-(1,3-dioxolan-2-yl)ethoxy]-2-fluoropyridine 2-(2-Bromoethyl)-1,3-dioxolane (2.49 ml, 19.9 mmol) and cesium carbonate (15.1 g, 46.4 mmol) were added to an N,N-dimethylacetamide solution (25 ml) of <strong>[55758-32-2]6-fluoropyridin-3-ol</strong> (1.5 g, 13.3 mmol), and stirred under a nitrogen atmosphere at 100C for 12 hours. The reaction solution was cooled with ice, water and ethyl acetate were added, and the organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate = 5:1 1 to 1:1) to obtain 5-[2-(1,3-dioxolan-2-yl)ethoxy]-2-fluoropyridine (2.43 g, yield: 86 %) as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With caesium carbonate; In N,N-dimethyl acetamide; at 100℃; for 15h;Inert atmosphere; | Preparation of 5-(2,2-diethoxyethoxy)-2-fluoroyridine Bromoacetaldehyde diethyl acetal (6.75 ml, 44.9 mmol) and cesium carbonate (30.9 g, 95.0 mmol) were added to an N,N-dimethylacetamide solution (60 ml) of <strong>[55758-32-2]6-fluoropyridin-3-ol</strong> (3.0 g, 24.9 mmol, purity: at most 94 %), and stirred under a nitrogen atmosphere at 100C for 15 hours. The reaction solution was cooled with ice, water was added, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate = 17:1 to 6:1) to obtain 5-(2,2-diethoxyethoxy)-2-fluoropyridine (5.67 g, yield: 99 %) as a pale yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In N,N-dimethyl acetamide; at 100℃; for 6h;Inert atmosphere; | Preparation of 2-fluoro-5-[3-(tetrahydro-2H-pyran-2-yloxy)bropoxy]byridine Bromoacetaldehyde diethyl acetal (2.29 ml, 13.3 mmol) and cesium carbonate (10.08 g, 30.9 mmol) were added to an N,N-dimethylacetamide solution (20 ml) of <strong>[55758-32-2]6-fluoropyridin-3-ol</strong> (1 g, 8.84 mmol), and stirred under a nitrogen atmosphere at 100C for 6 hours. The reaction solution was cooled to room temperature, water was added, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate = 7:1 1 to 3:1) to obtain a colorless oil (2.47 g) containing 2-fluoro-5-[3-(tetrahydro-2H-pyran-2-yloxy)propoxy]pyridine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 3h; | To a solution of 6-fluoropyridin-3-ol (75 g, 663 mmol) in DMF (265 mL, 663 mmol) were added potassium carbonate (59.7 g, 995 mmol) and iodomethane (108 g, 763 mmol). The resulting slurry was heated at 100 C for 3 hours. The reaction was diluted with water (1000 mL) and poured into a separatory funnel containing diethyl ether (1000 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (4 x 500 mL). The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide a yellow oil. This oil was diluted with 500 mL of DCM and concentrated to provide a yellow oil with a large amount of an off white precipitate. The mixture was filtered and the derived solid was washed well with DCM. The filtrate was concentrate to provide a mixture consisting of a yellow oil and an off white solid. The solid eas filtered, washing with DCM. Repeat this procedure again and then concentrated the filtrate to provide a yellow oil. The oil was taken up in 100 mL of ether and flashed through a plug of silica gel with 10:1 hexanes:ether to provide 2-fluoro-5-methoxypyridine as a yellow oil. | |
With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 3h; | Step 2: To a solution of 6-fluoropyridin-3-ol (75 g, 663 mmol) in DMF (265 mL, 663 mmol) were added potassium carbonate (59.7 g, 995 mmol) and iodomethane (108 g, 763 mmol). The resulting slurry was heated at 100 C for 3 hours. The reaction was diluted with water (1000 mL) and poured into a separatory funnel containing diethyl ether (1000 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (4 x 500 mL). The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide a yellow oil. This oil was diluted with 500 mL of DCM and concentrated to provide a yellow oil with a large amount of an off white precipitate. The mixture was filtered and the derived solid was washed well with DCM. The filtrate was concentrate to provide a mixture consisting of a yellow oil and an off white solid. The solid was filtered, washing with DCM. Repeat this procedure again and then concentrated the filtrate to provide a yellow oil. The oil was taken up in 100 mL of ether and flashed through a plug of silica gel with 10:1 hexanes:ether to provide 2-fluoro-5-methoxypyridine as a yellow oil. | |
With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 3h; | Step 2: To a solution of 6-fluoropyridin-3-ol (75 g, 663 mmol) in DMF (265 mL, 663 mmol) were added potassium carbonate (59.7 g, 995 mmol) and iodomethane (108 g, 763 mmol). The resulting slurry was heated at 100 C for 3 hours. The reaction was diluted with water (1000 mL) and poured into a separatory funnel containing diethyl ether (1000 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (4 x 500 mL). The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide a yellow oil. This oil was diluted with 500 mL of DCM and concentrated to provide a yellow oil with a large amount of an off white precipitate. The mixture was filtered and the derived solid was washed well with DCM. The filtrate was concentrate to provide a mixture consisting of a yellow oil and an off white solid. The solid was filtered, washing with DCM. Repeat this procedure again and then concentrated the filtrate to provide a yellow oil. The oil was taken up in 100 mL of ether and flashed through a plug of silica gel with 10:1 hexanes:ether to provide 2-fluoro-5-methoxypyridine as a yellow oil. |
With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 3h; | To a solution of 6-fluoropyridin-3-ol (75 g, 663 mmol) in DMF (265 mL, 663 mmol) were added potassium carbonate (59.7 g, 995 mmol) and iodomethane (108 g, 763 mmol). The resulting slurry was heated at 100 C for 3 hours. The reaction was diluted with water (1000 mL) and poured into a separatory funnel containing diethyl ether (1000 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (4 x 500 mL). The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide a yellow oil. This oil was diluted with 500 mL of DCM and concentrated to provide a yellow oil with a large amount of an off white precipitate. The mixture was filtered and the derived solid was washed well with DCM. The filtrate was concentrate to provide a mixture consisting of a yellow oil and an off white solid. The solid was filtered, washing with DCM. Repeat this procedure again and then concentrated the filtrate to provide a yellow oil. The oil was taken up in 100 mL of ether and flashed through a plug of silica gel with 10:1 hexanes:ether to provide 2-fluoro-5-methoxypyridine as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; | Preparation 5 2-Fluoro-5-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridine Add cesium carbonate (3 Eq, 53.05 mmoles; 17.2 g) to a solution of <strong>[55758-32-2]2-fluoro-5-hydroxypyridine</strong> (2.0 g, 1.00 Eq, 17.68 mmoles) in dimethylformamide (0.3 M; 762.37 mmoles; 59.0 mL), followed by 2-(2-bromoethoxy)tetrahydro-2H-pyran (17.7 mmoles, 3.7 g) and stir at room temperature overnight. Transfer to a separatory funnel and add EtOAc (500 mL). Wash organic layer, wash with water (300 mL) followed by brine (200 mL). Dry over Na2SO4, filter and concentrate. Purify the crude mixture by HPLC eluting with hexanes/EtOAc 7/3 to give 2-fluoro-5-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridine as a pale yellow oil (3.9 g, 16.2 mmoles; 91% yield). LCMS (Low) rt=1.8 min., M+1=242. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In N,N-dimethyl-formamide; at 50℃; for 2h; | 4-(6-Fluoro-pyridin-3-yloxy)-2-methyl-butan-2-ol A mixture of 6-fluoro-pyridin-3-ol (280 mg), toluene-4-sulfonic acid 3-hydroxy-3-methyl-butyl ester (721 mg), and cesium carbonate (807 mg) in N,N-dimethylformamide (10 mL) is heated to 50 C. for 2 h. The reaction mixture diluted with water and extracted with ethyl acetate. The combined extracts are dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30) to give the title compound. LC (method 5): tR=0.81 min; Mass spectrum (ESI+): m/z=200 [M+H]+. | |
With caesium carbonate; In N,N-dimethyl-formamide; at 50℃; for 2h; | A mixture of 6-fluoro-pyridin-3-ol (280 mg), toluene-4-sulfonic acid 3-hydroxy-3- methyl-butyl ester (721 mg), and cesium carbonate (807 mg) in N,N10 dimethylformamide (10 mL) is heated to 50 C for 2 h. The reaction mixture dilutedwith water and extracted with ethyl acetate. The combined extracts are dried overMgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel(cyclohexane/ethyl acetate 70:30) to give the title compound. LC (method 5): tR =0.81 mm; Mass spectrum (ESl): mlz = 200 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49%; 24% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 6h; | N-[2-(Bromomethyl)-3-fluoro-allyl]carbamic acid tert-butyl ester 1a (0.70 g, 2.6 mmol) was dissolved in N,N-dimethylformamide (7 mL).Potassium carbonate (0.44 g, 3.2 mmol) and <strong>[55758-32-2]6-fluoropyridin-3-ol</strong> 5a (0.32 g, 2.8 mmol) were added, and the mixture was reacted at room temperature for 6 hr, then quenched with water (5 mL).Extracted with ethyl acetate (20 mL) and EtOAc (EtOAc)The residue was dried over anhydrous sodium sulfate (MgSO4).The title compound 5b (0.38 g, yield 49%) and 5c (0.19 g, yield 24%) were obtained as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.1 mg | With ((2-dicyclohexylphosphino-2',4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II) methanesulfonate); caesium carbonate; In 1,4-dioxane; at 90℃;Inert atmosphere; | A 1 dram vial was charged with tert-butyl ((lR,4R,7R)-2-(2-(6-bromo-l- (0705) (cy clopropylmethyl)-lH-indol-2-yl)-7-methoxy-l -methyl- l H-benzo[d]imidazole-5- carbonyl)-2-azabicyclo[2.2. l]heptan-7-yi)carbamate (0.037 g, 0.040 mmol), 2-fiuoro-5- hydroxypyridine (5.42 mg, 0.048 mmol), cesium carbonate (0.020 g, 0.060 mmol) and Rockphos Pd G3 (3.35 mg, 3.99 pmol) in dioxane (1 mL). The vial was capped and the reaction mixture was made anaerobic by a pump / backfill with nitrogen cycle (5X). The reaction was set to stir at 90 C overnight. After cooling, the mixture was diluted with EtOAc, dried (MgS04), filtered, and concentrated. The resulting residue was dissolved in dichloromethane (1 mL) and treated with TFA (0.5 ml, 6.49 mmol). Mixture was stirred at rt for 90 min before it was concentrated. The residue was dissolved in DMF, filtered and purified via preparative LC/MS with the following conditions: Column: XBridge C l 8, 19 x 200 mm, 5-mth particles; Mobile Phase A: 5;95 acetonitrile: water with 10-mM ammonium acetate: Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 26-66% B over 20 minutes, then a 4-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The purified material was then diluted with DMF, treated with Si-Pyridine and shaken for a minimum of 2 h. The resulting mixture was filtered and concentrated via centrifugal evaporation to give ((IR,4R,7RV7-amino~2~ (0706) azabicycJo[2.2.1]heptan-2-yl)(2-(l-(cyclopropyJmethyl)-6-((6-fluoropyridin-3-yl)oxy)- lH-indol-2-yl)-7-m ethoxy- l-methyl-lH-benzo[d]imidazol-5-yl)methanone (4.1 mg): fit NMR (500 MHz, DM 80-dr,) d 8.03 (br s, 1H), 7.72 (br d, J=8.5 Hz, 1H), 7.68 (br t, .7=6.0 Hz, i l l ). 7 44 (br s, 1 1 1 ), 7.34 (s, 1 1 1), 7.21 (br dd, .7=8.7, 2.9 Hz, i l l ). 7 06 (s, i l l ). 6 95 - 6.90 (m, 2H), 4.37 (br d, .7=6.4 Hz, 21 1). 4.10 (s, 31 1). 3.98 (s, 31 1 ). 3.75 (br s, 1H), 3.66 - 3.48 (m, 1H), 3.17 (s, 1H), 3.08 - 2.99 (m, 1H), 2.21 (br s, 1H), 2.04 - 1.91 (m, 2H), 1.74 (br t, ./ 9.5 Hz, 1H), 1.48 - 1 40 (m, 1 H), 1.23 (s, 2H), 1.04 - 0.94 (m, 1H), 0.26 (br d, ,7=7.9 Hz, 2H), -0.02 (br s, 2H); LC/MS (M+H) = 581.3; Retention Time = 1.75 min (Method 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 60℃; for 2h; | To a solution of <strong>[55758-32-2]6-fluoropyridin-3-ol</strong> (185 mg, 1.64 mmol) and ieri-butyl (2S,4S)-4-hydroxy-2- methylpyrrolidine- 1 -carboxylate (300 mg, 1.49 mmol) in THF (15.0 mL) were added DIAD (603 mg, 2.98 mmol) and triphenylphosphine (782 mg, 2.98 mmol). The mixture was stirred at 60C for 2 hrs. The solvent was removed and the residue was purified by column chromatograph on silica gel eluted (Petroleum ether/EtOAc = 3/1) to provide the title compound (92.0 mg, 21% yield). 1HNMR: (400 MHz, CDCl3) d 7.78-7.79 (m, 1H), 7.27-7.31 (m, 1H), 6.87 (dd, 7=8.8, 3.2 Hz, 1H), 4.82-4.84 (m, 1H), 4.03-4.09 (m, 1H), 3.75-3.76 (m, 1H), 3.62-3.64 (m, 1H), 2.33-2.36 (m, 1H), 1.93-1.96 (m, 1H), 1.47 (s, 9H), 1.32 (d, 7=6.4 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 60℃; | To a solution of 6-fluoropyri din-3 -ol (15.0 g, 132.7 mmol) in dry THF (600 ml) at 0C, were successively added 2-indanol (23.0 g, 171.6 mmol), triphenylphosphine (45.0 g, 172.6 mmol) and DIAD (34 ml, 171.6 mmol). The mixture was stirred 3 days at RT and 3h at 60C. After cooling and evaporation of the solvent, the crude was purified by FC (320 g, Si02, cyclohexane/AcOEt 100:0 70:30) leading to the expected product as a yellow powder (15.7 g, 52%). NMR (300 MHz, DMSO-r) d 7.88 (t, J= 2.1 Hz, 1H), 7.63-7.57 (m, 1H), 7.26-7.23 (m, 2H), 7.17-7.08 (m, 3H), 5.29-5.24 (m, 1H), 3.35 (dd, J = 17.1, 6.0 Hz, 2H), 3.00 (dd, J= 17.1, 2.1 Hz, 2H). ESIMS m/z [M+H]+ 230.2. |
Tags: 55758-32-2 synthesis path| 55758-32-2 SDS| 55758-32-2 COA| 55758-32-2 purity| 55758-32-2 application| 55758-32-2 NMR| 55758-32-2 COA| 55758-32-2 structure
[ 1805602-80-5 ]
6-Fluoro-3-methoxypyridin-2-amine
Similarity: 0.71
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