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CAS No. : | 518058-84-9 | MDL No. : | MFCD25977063 |
Formula : | C16H13FN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | TUIHIKXCMCXXJG-UHFFFAOYSA-N |
M.W : | 284.29 | Pubchem ID : | 21014417 |
Synonyms : |
|
Chemical Name : | 5-Fluoro-N-(3-hydroxybenzyl)-1H-indole-2-carboxamide |
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 15 |
Fraction Csp3 : | 0.06 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 77.76 |
TPSA : | 65.12 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.98 cm/s |
Log Po/w (iLOGP) : | 1.79 |
Log Po/w (XLOGP3) : | 2.9 |
Log Po/w (WLOGP) : | 3.21 |
Log Po/w (MLOGP) : | 2.16 |
Log Po/w (SILICOS-IT) : | 3.46 |
Consensus Log Po/w : | 2.7 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.69 |
Solubility : | 0.0575 mg/ml ; 0.000202 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.93 |
Solubility : | 0.0336 mg/ml ; 0.000118 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.91 |
Solubility : | 0.000353 mg/ml ; 0.00000124 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.92 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: C17H15FN2O2 With boron tribromide In dichloromethane at 0 - 20℃; for 3h; Stage #2: With hydrogenchloride; water In dichloromethane at 0℃; | 1.B.e.b (b) Demethylation; A mixture of the methoxy intermediate (5 g, 16.7 mmol) and CH2Cl2 (80 mL) was placed in a multi neck flask equipped with a dropping funnel and a thermometer. The flask was cooled to 0° C. in an ice/salt bath. A solution of BBr3 in CH2Cl2 (80 mL) was added dropwise while keeping the temperature less than 5° C. The mixture was stirred at room temperature for 3 hours. After addition of ice and 3M HCl (200 mL), the mixture was left to stir overnight. The precipitated solid product was collected by filtration, washed with water, and dried. Crystallization from CH2Cl2 and MeOH furnished 4.2 g (88%) of compound 1a: MP 213° C.; 1H NMR (DMSO-d6, 400 MHz) δ 11.68 (br, 1H), 9.31 (br, 1H), 9.01 (t, 1H, J=6.0 Hz), 7.39 (complex, 2H), 7.14 (s, 1H), 7.09 (dd, 1H, J=8.0 and 7.7 Hz), 7.02 (ddd, 1H, J=9.2, 8.9 and 2.5 Hz), 6.72 (d, 2H, J=7.3 Hz), 6.61 (d, 1H, J=8.4 Hz), 4.41 (d, 2H, J=5.9 Hz), HRMS (EI): Required M+ for C16H13FN2O2, 284.0956; Found, 284.0960; Anal. (C16H13FN2O2) C, 67.60; H, 4.61; F, N, 9.85; Found C, 67.50; H, 4.65; F, N, 9.76. |