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CAS No. : | 348-37-8 | MDL No. : | MFCD03095203 |
Formula : | C11H10FNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KOLXHQLPMICACW-UHFFFAOYSA-N |
M.W : | 207.20 | Pubchem ID : | 15370496 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.18 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 54.34 |
TPSA : | 42.09 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) : | -5.65 cm/s |
Log Po/w (iLOGP) : | 2.3 |
Log Po/w (XLOGP3) : | 2.7 |
Log Po/w (WLOGP) : | 2.9 |
Log Po/w (MLOGP) : | 2.08 |
Log Po/w (SILICOS-IT) : | 3.12 |
Consensus Log Po/w : | 2.62 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.07 |
Solubility : | 0.176 mg/ml ; 0.000848 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.24 |
Solubility : | 0.12 mg/ml ; 0.00058 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.05 |
Solubility : | 0.0185 mg/ml ; 0.0000891 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.97 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H317 | 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 |
---|---|---|
89% | Stage #1: With sodium hydroxide In ethanol for 3 h; Reflux Stage #2: With acetic acid In ethanol; waterCooling with ice |
General procedure: A mixture of compound 3a (33.5 g, 0.15 mol), 4percent NaOH solution (335 mL) and ethanol (335 mL) was heated to reflux for 3 h. Upon cooling to room temperature, the mixture was poured into ice-water, adjusted to pH 5 with glacial acetic acid, and then the precipitate was collected by filtration. 4a was obtained as a white solid (26.4 g, 90percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With iron In ethanol; acetic acid for 3.5 h; Heating / reflux | (3-2) Ethyl 3-(4-fluoro-2-nitrophenyl)-2-oxopropanoate (5.51 g, 21.6 mmol) obtained in Reference Example (3-1) was dissolved in a mixed solvent of ethanol-acetic acid (1:1, 84 ml), and iron powder (10.9 g, 144 mmol) was added thereto, followed by heating under reflux for 3.5 hours. After the reaction mixture was diluted with tetrahydrofuran, the insolubles were filtered through Celite, and the residue obtained by concentrating the filtrate under reduced pressure was purified by silica gel column chromatography (elution solvent: methylene chloride/acetone=15/1) to obtain ethyl 6-fluoro-1H-indole-2-carboxylate (3.62 g, yield: 81percent). 1H-NMR (400MHz, CDCl3): δ 8.89 (1H, br. s), 7.61 (1H, dd, J = 8.8, 5.5 Hz), 7.20 (1H, m), 7.09 (1H, dd, J = 9.4, 2.0 Hz), 6.94 (1H, ddd, J = 9.4, 8.8, 2.0 Hz), 4.41 (2H, q, J = 7.0 Hz), 1.42 (3H, t, J = 7.0 Hz).; (9-6) Ethyl 3-(4-fluoro-2-nitrophenyl)-2-oxopropanoate (5.51 g, 21.6 mmol) obtained in Reference Example (9-5) was dissolved in a mixed solvent of ethanol-acetic acid (1:1, 84 ml), and iron powder (10.9 g, 144 mmol) was added thereto, followed by heating under reflux of the mixture for 3.5 hours. The temperature of the reaction mixture was returned to room temperature, and the mixture was diluted with tetrahydrofuran. The insolubles were removed by filtration using Celite, and the filtrate was concentrated under reduced pressure. The thus obtained residue was purified by silica gel column chromatography (elution solvent: methylene chloride/acetone=15/1) to obtain ethyl 6-fluoro-1H-indole-2-carboxylate as yellow crystals (3.62 g, yield: 81percent). 1H-NMR (400MHz, CDCl3) : δ 8.89 (1H, br. s), 7.61 (1H, dd, J = 8.8, 5.5 Hz), 7.20 (1H, m), 7.09 (1H, dd, J = 9.4, 2.0 Hz), 6.94 (1H, ddd, J = 9.4, 8.8, 2.0 Hz), 4.41 (2H, q, J = 7.0 Hz), 1.42 (3H, t, J = 7.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.1% | at 105℃; for 2 h; | 6-Fluoro-1H-indole-2-carboxylic acid 12a (2.00g, 11.16mmol) was dissolved in 60mL of absolute ethanol, 10mL of 98percent concentrated sulfuric acid was added, the reaction liquid was heated to 105°C and was reacted for 2 hours. The pH of the reaction solution was adjusted to 7 to 8 with 1M NaOH, the solution was extracted with ethyl acetate (150mL*3). The combined organic phases were washed with saturated sodium chloride solution (2000mL*3) then saturated ammonium chloride solution (200mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain ethyl 6-fluoro-1H-indole-2-carboxylate 12b (2.24g, dark yellow solid), yield: 94.1 percent. MS m / z (ESI): 207.9 [M + 1] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With polyphosphoric acid In toluene for 6 h; Reflux | To a 500 mL flask was added toluene (200 mL)Was added thereto, and the compound(E) -ethyl-2- (2- (3-fluorophenyl) hydrazano) propanoate (22.5 g, 100.34 mmol).Then, polyphosphoric acid (120 g) was added thereto,The reflux reaction was allowed to proceed for 6 hours.After the reaction was completed, the reaction solution was cooled to 50 DEG C, and only the toluene layer was separated.The separated toluene layer was concentrated under reduced pressure.Then toluene (50 mL) was added to the solid formed, and the mixture was refluxed for 1 hour and then cooled to room temperature.The re-crystallized solid was then filtered to give ethyl-6-fluoro-lH-indole-2-carboxylate (7.2 g, 34.7 mmol, 34percent). |
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